Abstract
This review profiles ten marketed pharmaceuticals approved by the US Food and Drug Agency within the last five years that feature aliphatic fluorination – a key structural feature pivotal to their biological activity. These include ivosidenib, developed for the treatment of acute myeloid leukemia and cholangiocarcinoma (bile duct cancer); ubrogepant, approved for the acute treatment of migraines; asciminib, prescribed for the treatment of chronic myeloid leukemia in the chronic phase; omaveloxolone, used in the treatment of Friedreich’s ataxia, a rare genetic disorder causing progressive damage to the spinal cord, peripheral nerves, and brain; flurpiridaz (18F), a radioactive diagnostic agent for myocardial perfusion imaging by positron emission tomography; upadacitinib, designed to address several inflammatory and autoimmune conditions, including rheumatoid arthritis, psoriatic arthritis, atopic dermatitis, ulcerative colitis, Crohn’s disease, ankylosing spondylitis, and non-radiographic axial spondyloarthritis; tezacaftor, approved for the treatment of cystic fibrosis as an effective remedy; alpelisib, prescribed for the treatment of breast cancer, effectively inhibiting tumor growth and abnormal cell proliferation; pretomanid, used in combination therapies for the treatment of extensively drug-resistant and multi-drug-resistant tuberculosis; and atogepant, approved for the preventive treatment of migraines in adults, targeting both episodic and chronic migraines. Molecules featuring aliphatic fluorination present challenges due to higher production costs and the complexity of predicting their biological profiles. However, the undeniable medicinal benefits of aliphatic fluorination invigorate this area of research, paving the way for the development of more innovative drugs to enter the pharmaceutical market. Beyond the incorporation of aliphatic fluorine atoms, six of the pharmaceuticals discussed in this review feature residues of amino acids or their derivatives as pivotal structural design elements. Another characteristic shared by all these drugs is their chirality, with each molecule possessing between one and six stereogenic carbons. Special attention should be directed toward the phenomenon of self-disproportionation of enantiomers (SDE), a behavior observed in enantiomerically enriched compounds. The SDE properties of chiral drugs, particularly those containing fluorine and/or amino acid residues, represent a vital public safety concern, necessitating rigorous evaluation of enantiomeric purity. Additionally, caution should be exercised in light of growing public concerns over the potential harmful effects of fluorine on human health. Since fluoride is recognized as the final metabolite of organic fluorinated compounds, patients prescribed fluorine-containing drugs should consult their physicians about non-fluorinated alternatives where available or take steps to limit fluoride exposure from other sources, such as fluoridated water and industrially produced foods treated with fluorinated agrochemicals. Despite these concerns, it remains an undeniable fact that fluorine-containing drugs are indispensable in modern medicine. They provide life-saving treatments, improve quality of life, and drive medical innovation addressing urgent health challenges and laying the foundation for future advancements in healthcare.
References
Mohammed M.A., Moles R.J., Chen T.F. Impact of Pharmaceutical Care Interventions on Health-Related Quality-of-Life Outcomes: A Systematic Review and Meta-analysis. Ann. Pharmacother. 2016. 50(10): 862–881.
doi:10.1177/1060028016656016.
Lichtenberg F.R., Virabhak S. Pharmaceutical‐embodied technical progress, longevity, and quality of life: drugs as ‘Equipment for Your Health’. Manag. Decis. Econ. 2007. 28(4–5): 371–392.
doi.org/10.1002/mde.1347.
Cook M.A., Wright G.D. The past, present, and future of antibiotics. Sci. Transl. Med. 2022. 14(657): 7793.
doi: 10.1126/scitranslmed.abo77.
Barot S., Patel H., Yadav A., Ban I. Recent advancement in targeted therapy and role of emerging technologies to treat cancer. Med. Oncol. 2023. 40(11): 324.
doi.org/10.1007/s12032-023-02184-6.
Zuvekas S.H. Prescription drugs and the changing patterns of treatment for mental disorders, 1996–2001. Health Affairs. 2005. 24(1): 195–205.
doi.org/10.1377/hlthaff.24.1.195.
Lee E.K., Maheshwary S., Mason J., Glisson W. Decision support system for mass dispensing of medications for infectious disease outbreaks and bioterrorist attacks. Ann. Operat. Res. 2006. 148: 25–53.
doi.org/10.1007/s10479-006-0087-7.
Wang J., Sánchez-Roselló M., Aceña J.L. et al. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001–2011). Chem. Rev. 2014. 114(4): 2432–2506.
doi.org/10.1021/cr4002879.
Shah P., Westwell A.D. The role of fluorine in medicinal chemistry. J. Enz. Inhib. Med. Chem. 2007. 22(5): 527–540.
doi.org/10.1080/14756360701425014.
Swallow S. Fluorine in medicinal chemistry. Prog. Med. Chem. 2015. 54: 65–133.
doi.org/10.1016/bs.pmch.2014.11.001.
Filler R., Saha R. Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights. Future Med. Chem. 2009. 1(5): 777–791.
doi.org/10.4155/fmc.09.65.
O’Hagan D., Young R.J. Future challenges and opportunities with fluorine in drugs? Med. Chem. Res. 2023. 32(7): 1231–1234.
doi.org/10.1007/s00044-023-03094-y.
Shukla A.K., Kumar U. Positron emission tomography: An overview. J. Med. Phys. 2006. 31(1): 13–21.
doi: 10.4103/0971-6203.25665.
Couturier O., Luxen A., Chatal J.F. et al. Fluorinated tracers for imaging cancer with positron emission tomography. Eur. J. Nuc. Med. Molec. Imag. 2004. 31: 1182–1206.
doi.org/10.1007/s00259-004-1607-9.
Avril N., Rose C.A., Schelling M. et al. Breast imaging with positron emission tomography and fluorine-18 fluorodeoxyglucose: use and limitations. J. Clin. Oncol. 2000. 18(20): 3495–3502.
doi.org/10.1200/JCO.2000.18.20.3495.
Makarem A., Klika K.D., Litau G. et al. HBED-NN: A bifunctional chelator for constructing radiopharmaceuticals. J. Org. Chem. 2019. 84(11): 7501–7508.
doi.org/10.1021/acs.joc.9b00832.
Da Pieve C., Makarem A., Turnock S. et al. Thiol-Reactive PODS-Bearing Bifunctional Chelators for the Development of EGFR-Targeting [18F]AlF-Affibody Conjugates. Molecules. 2020. 25(7): 1562.
doi.org/10.3390/molecules25071562.
Klika K.D., Da Pieve C., Kopka K. et al. Synthesis and application of a thiol-reactive HBED-type chelator for development of easy-to-produce Ga-radiopharmaceutical kits and imaging probes. Org. Biomol. Chem. 2021. 19(8): 1722–1726.
doi.org/10.1039/D0OB02513E.
O’Hagan D. Fluorine in health care: Organofluorine containing blockbuster drugs. J. Fluor. Chem. 2010. 131(11): 1071–1081.
doi.org/10.1016/j.jfluchem.2010.03.003.
Han J., Remete A.M., Dobson L.S. et al. Next generation organofluorine containing blockbuster drugs. J. Fluor. Chem. 2020. 239: 109639.
doi.org/10.1016/j.jfluchem.2020.109639.
Xu P., Zhu L., Zhang D. et al. Design and synthesis of fluorine aromatic scaffolds containing drugs approved by the US FDA from 2002 to 2022. Results Chem. 2024. 7: 101446.
doi.org/10.1016/j.rechem.2024.101446.
Imeni S., Makarem A., Javahershenas R. Recent Advances in Multicomponent Electro‐Organic (Electrochemical) Synthesis of Heterocycles. Asian J. Org. Chem. 2023. 12(8): e202300303.
doi.org/10.1002/ajoc.202300303.
Javahershenas R., Makarem A., Klika K.D. Recent advances in microwave-assisted multicomponent synthesis of spiro heterocycles. RSC Adv. 2024. 14(8): 5547–5565.
doi: 10.1039/D4RA00056K.
Qiu X.-L., Yue X., Qing F.-L. Fluorine‐Containing Chiral Drugs. In: Chiral Drugs: Chemistry and Biological Action. Lin G.-Q., You Q.-D., Cheng J.-F. Eds., 2011. 26: 195–251.
https://doi.org/10.1002/9781118075647.ch5.
Han J., Wzorek A., Dhawan G. et al. Chiral fluorine-containing pharmaceuticals, Ukr. Chem. J. 2025. 91(2): 55-90.
doi: 10.33609/2708-129X.91.2.2025.55-90.
Zhou Y., Wang J., Gu Z. et al. Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas. Chem. Rev. 2016. 116(2): 422–518.
doi: 10.1021/acs.chemrev.5b00392.
Mei H., Han J., Fustero S. et al. Fluorine‐Containing Drugs Approved by the FDA in 2018. Chem.–Eur. J. 2019. 25(51): 11797–11819.
doi: 10.1002/chem.201901840.
Mei H., Remete A.M., Zou Y. et al. Fluorine-containing drugs approved by the FDA in 2019. Chin. Chem. Lett. 2020. 31(9): 2401–2413.
doi: 10.1016/j.cclet.2020.03.050.
Wang Q., Bian Y., Dhawan G. et al. FDA approved fluorine-containing drugs in 2023. Chin. Chem. Lett. 2024. 35(11): 109780.
doi: 10.1016/j.cclet.2024.109780.
Yu Y., Liu A., Dhawan G. et al. Fluorine-containing pharmaceuticals approved by the FDA in 2020: Synthesis and biological activity. Chin. Chem. Lett. 2021. 32(11): 3342–3354.
doi: 10.1016/j.cclet.2021.05.042.
He J., Li Z., Dhawan G. et al. Fluorine-containing drugs approved by the FDA in 2021. Chin. Chem. Lett. 2023. 34(1): 107578.
doi: 10.1016/j.cclet.2022.06.001.
Du Y., Bian Y., Baecker D. et al. Fluorine in the Pharmaceutical Industry: FDA‐Approved Fluorine‐Containing Drugs in 2024. Chem.—Eur. J. 2025. e202500662.
doi.org/10.1002/chem.202500662.
Zhu W., Wang J., Wang S. et al. Recent advances in the trifluoromethylation methodology and new CF3-containing drugs. J. Fluor. Chem. 2014. 167: 37–54.
doi.org/10.1016/j.jfluchem.2014.06.026.
Rizzo C., Amata S., Pibiri I. et al. FDA-approved fluorinated heterocyclic drugs from 2016 to 2022. Int. J. Mol. Sci. 2023. 24(9): 7728.
doi.org/10.3390/ijms24097728.
He J., Wang C., Mei H. et al. Visible-light-promoted cyclization of 3-indolylallylamides enabling synthesis of tetrahydrocarbolinones. Tetrahedron. 2024. 150: 133776.
doi.org/10.1016/j.tet.2023.133776.
Du Y., Mei H., Makarem A. et al. Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters. Beilstein J. Org. Chem. 2024. 20(1): 212–219.
doi.org/10.3762/bjoc.20.21.
Javahershenas R., Mei H., Koley M. et al. Recent advances in the multicomponent synthesis of heterocycles using 5-aminotetrazole. Synthesis. 2024. 56(16): 2445–2461.
doi: 10.1055/s-0042-1751526.
Abbas A.A., Farghaly T.A., Dawood K.M. Recent progress in therapeutic applications of fluorinated five-membered heterocycles and their benzo-fused systems. RSC Adv. 2024. 14(46): 33864–33905.
doi: 10.1039/D4RA05697C.
Lyutenko N.V., Han J., Wzorek A. et al. Carbon nanotubes-catalyzed synthesis of fluorine-containing heterocycles, Ukr. Chem. J. 2024. 90(6): 71–86.
doi: 10.33609/2708-129X.90.6.2024.71-86.
Yamada T., Okada T., Sakaguchi K. et al. Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide. Org. Lett. 2006. 8(24): 5625–5628.
doi: 10.1021/ol0623668.
Soloshonok V.A., Hayashi T. Gold(I)-catalyzed asymmetric aldol reaction of fluorinated benzaldehydes with α-isocyanoacetamide. Tetrahedron: Asymmetry. 1994. 5(6): 1091–1094.
doi: 10.1016/0957-4166(94)80059-6.
Wang Q., Han J., Sorochinsky A. et al. The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine. Pharmaceuticals. 2022. 15(8): 999.
doi.org/10.3390/ ph150809991847558.
Han J., Wzorek A. Dhawan G. et al. New drugs on the pharmaceutical market containing fluorine and residues of tailor-made amino acids. Ukr. Chem. J. 2024. 90(9): 31–56.
doi: 10.33609/2708-129X.90.9.2024.31-56.
Yin Z., Hu W., Zhang W. et al. Tailor-made amino acid-derived pharmaceuticals approved by the FDA in 2019. Amino Acids. 2020. 52(9): 1227–1261.
doi: 10.1007/s00726-020-02887-4.
Mei H., Han J., White S. et al. Tailor-made amino acids and fluorinated motifs as prominent traits in modern pharmaceuticals. Chem.–Eur. J. 2020. 26(50): 11349–11390.
doi: 10.1002/chem.202000617.
Ellis T.K., Hochla V.M., Soloshonok V.A. Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent. J. Org. Chem. 2003. 68(12): 4973–4976.
doi.org/10.1021/jo030065v.
Han J., Konno H., Sato T. et al. Peptidomimetics and Peptide-Based Blockbuster Drugs. Curr. Org. Chem. 2021. 25(14): 1627–1658.
doi: 10.2174/1385272825666210610155047.
Han J., Konno H., Sato T., Soloshonok V.A., Izawa K. Tailor-made amino acids in the design of small-molecule blockbuster drugs. Eur. J. Med. Chem. 2021. 220: 113448.
doi: 10.1016/j.ejmech.2021.113448.
Liu A., Han J., Nakano A. et al. New pharmaceuticals approved by FDA in 2020: Small-molecule drugs derived from amino acids and related compounds. Chirality. 2022. 34(1): 86–103.
doi: 10.1002/chir.23376.
Wang N., Mei H., Dhawan G. et al. New Approved Drugs Appearing in the Pharmaceutical Market in 2022, Featuring Fragments of Tailor-Made Amino Acids and Fluorine. Molecules. 2023. 28(9): 3651.
doi: 10.3390/molecules28093651.
Han J., Wzorek A., Dhawan G. et al. New drugs appearing on the market in 2023: molecules containing fluorine and fragments of tailor-made amino acids. Ukr. Bioorg. Acta. 2024. 19(1): 3–20.
doi: 10.15407/bioorganica2024.01.003.
Shibata N., Nishimine T., Shibata N. et al. Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids. Chem. Commun. 2012. 48(34): 4124–4126.
doi: 10.1039/C2CC30627A.
Soloshonok V.A., Ohkura H., Yasumoto M. Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid: Part II. Enantioselective biomimetic transamination of 4,4,4-trifluoro-3-oxo-N-[(R)-1-phenylethyl)butanamide. J. Fluor. Chem. 2006. 127(7): 930–935.
doi: 10.1016/j.jfluchem.2006.04.004.
Wzorek A., Sorochinsky A.E., Klika K.D. et al. Asymmetric synthesis of chi-constrained glutamic acids and related compounds via Michael addition reactions. Ukr. Chem. J. 2024. 90(8): 83–108.
doi: 10.33609/2708-129X.90.8.2024.83-108.
Han J., Liu H., Wang J. et al. Hamari’s contribution to the asymmetric synthesis of tailor-made amino acids. Ukr. Chem. J. 2024. 90(10): 88–134.
doi: 10.33609/2708-129X.90.10.2024.88-134.
Hutt A.J., Tan S.C. Drug Chirality and its Clinical Significance. Drugs. 1996. 52(5): 1–12.
doi.org/10.2165/00003495-199600525-00003.
Lin G.Q., You Q.D., Cheng J.F. Chiral drugs. In: Chemistry and Biological Action. Wiley, 2011.
doi:10.1002/9781118075647.
Brooks W.H., Guida W.C., Daniel K.G. The significance of chirality in drug design and development. Curr. Top. Med. Chem. 2011. 11(7): 760–770.
doi: 10.2174/156802611795165098.
Ceramella J., Iacopetta D., Franchini A. et al. A look at the importance of chirality in drug activity: Some significative examples. Appl. Sci. 2022. 12(21): 10909.
doi.org/10.3390/app122110909.
Crossley R.J. Chirality and biological activity of drugs. CRC Press, 1995.
Calcaterra A., D’Acquarica I. The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds. J. Pharmaceut. Biomed. Anal. 2018. 147: 323–340.
doi.org/10.1016/j.jpba.2017.07.008.
Cai C., Soloshonok V.A., Hruby V.J. Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-Enoyl)oxazolidin-2-ones. A case of electron donor–acceptor attractive interaction-controlled face diastereoselectivity. J. Org. Chem. 2001. 66(4): 1339–1350.
doi: 10.1021/jo0014865.
Soloshonok V.A., Hayashi T. Gold(I)-catalyzed asymmetric aldol reaction of methyl isocyanoacetate with fluorinated benzaldehydes. Tetrahedron Lett. 1994. 35(17): 2713–2716.
doi: 10.1016/S0040-4039(00)77013-4.
Bravo P., Guidetti M., Viani F. et al. Chiral sulfoxide controlled asymmetric additions to C N double bond. An efficient approach to stereochemically defined α-fluoroalkyl amino compounds. Tetrahedron. 1998. 54(42): 12789–12806.
doi: 10.1016/S0040-4020(98)00779-0.
Bravo P., Farina A., Kukhar V.P. et al. Stereoselective additions of α-lithiated alkyl-p-tolylsulfoxides to N-PMP fluoroalkyl aldimines. An efficient approach to enantiomerically pure fluoro amino compounds. J. Org. Chem. 1997. 62(11): 3424–3425.
doi: 10.1021/jo970004v.
Soloshonok V.A., Kukhar V.P. Biomimetic transamination of α-keto perfluorocarboxylic esters. An efficient preparative synthesis of β,β,β-trifluoroalanine. Tetrahedron. 1997. 53(25): 8307–8314.
doi: 10.1016/S0040-4020(97)00517-6.
Dhillon S. Ivosidenib: first global approval. Drugs. 2018. 78(14): 1509–1516
doi.org/10.1007/s40265-018-0978-3.
Buskes M.J., Coffin A., Troast D.M. et al. Accelerating drug discovery: synthesis of complex chemotypes via multicomponent reactions. ACS Med. Chem. Lett. 2023. 14(4): 376–385.
doi.org/10.1021/acsmedchemlett.3c00012.
Wang X., Wang Q.-G., Luo Q.-L. Synthesis of Isonitriles from N-Substituted Formamides Using Triphenylphosphine and Iodine. Synthesis. 2015. 47: 49–54.
doi: 10.1055/s-0034-1379111.
Lemieux R.M., Popovici-Muller J., Travins J.Z. et al. WO 2013/107291 Al, 2013.
Patel D.B., Parmar J.A., Patel S.S. et al. Recent advances in ester synthesis by multi-component reactions (MCRs): A review. Curr. Org. Chem. 2021. 25(5): 539–553.
doi.org/10.2174/1385272825666210111111805.
Guram A.S., Rennels R.A., Buchwald S.L. A simple catalytic method for the conversion of aryl bromides to arylamines. Angew. Chem., Int. Ed. 1995. 34(12): 1348–1350.
doi.org/10.1002/anie.199513481.
Hartwig J.F. Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design. Synlett. 1997:329–340
doi: 10.1055/s-1997-789.
Marek W.K., Lee J.W., Seidel-Morgenstern A., Antos D. Separation of nonracemic mixtures of enantiomers by achiral simulated moving bed chromatography. Separat. Purif. Technol. 2025. 361: 131497.
doi.org/10.1016/j.seppur.2025.131497.
Wzorek A., Klika K.D., Han J. et al. Enantiomer Purification Through Achiral Chromatography: Integrating Simulated Moving Bed and Self-Disproportionation of Enantiomers. Ukr. Chem. J., 2025. 91(3): 34-48.
doi.org/10.33609/2708-129X.91.3.2025.34-48.
Bell I.M., Fraley M.E., Gallicchio S.N. et al. US2010/0122899, 2012.
Holland P.R., Goadsby P.J. Targeted CGRP small molecule antagonists for acute migraine therapy. Neurotherapeutics. 2018. 15(2): 304–312.
doi.org/10.1007/s13311-018-0617-4.
Martelletti P., Giamberardino M.A. Advances in orally administered pharmacotherapy for the treatment of migraine. Exp. Opin. Pharmacother. 2019. 20(2): 209–218.
doi.org/10.1080/14656566.2018.1549223.
Lipton R.B., Dodick D.W., Ailani J. et al. Effect of ubrogepant vs placebo on pain and the most bothersome associated symptom in the acute treatment of migraine: the ACHIEVE II randomized clinical trial. JAMA. 2019. 322(19): 1887–1898.
doi: 10.1001/jama.2019.16711.
Bell I.M., Fraley M.E., Gallicchio S.N. et al. PCT/US2011/060081, 2012.
Chen F., Molinaro C., Wuelfing W.P. et al. PCT/US2013/030692, 2013.
Belyk K.M., Cleator E., Kuo S.C. et al. PCT/US2013/030696, 2013.
Yasuda N., Cleator E., Kosjek B. et al. Practical asymmetric synthesis of a calcitonin gene-related peptide (CGRP) receptor antagonist ubrogepant. Org. Proc. Res. Devel. 2017. 21(11): 1851–1858.
doi.org/10.1021/acs.oprd.7b00293.
Deeks E.D. Asciminib: first approval. Drugs. 2022. 82(2): 219–226.
doi.org/10.1007/s40265-021-01662-3.
Schoepfer J., Jahnke W., Berellini G. et al. Discovery of asciminib (ABL001), an allosteric inhibitor of the tyrosine kinase activity of BCR-ABL1. J. Med. Chem. 2018. 61(18): 8120–8135.
doi.org/10.1021/acs.jmedchem.8b01040.
Vaz R.J., Li Y., Rampe D. Human ether-a-go-go related gene (HERG): a chemist’s perspective. Prog. Med. Chem. 2005. 43: 1–8.
doi.org/10.1016/S0079-6468(05)43001-5.
Kurzrock R., Gutterman J.U., Talpaz M. The molecular genetics of Philadelphia chromosome–positive leukemias. New Eng. J. Med. 1988. 319(15): 990–998.
doi: 10.1056/NEJM198810133191506.
Schuld P., Grzesiek S., Schlotte J. et al. Structural and biochemical studies confirming the mechanism of action of asciminib, an agent specifically targeting the ABL myristoyl pocket (STAMP). Blood. 2020. 136: 34–35.
doi.org/10.1182/blood-2020-140968.
Wylie A.A., Schoepfer J., Jahnke W. et al. The allosteric inhibitor ABL001 enables dual targeting of BCR–ABL1. Nature. 2017. 543(7647): 733–737.
doi.org/10.1038/nature21702.
Milojkovic D., Apperley J. Mechanisms of resistance to imatinib and second-generation tyrosine inhibitors in chronic myeloid leukemia. Clin. Cancer Res. 2009. 15(24): 7519–727.
doi.org/10.1158/1078-0432.CCR-09-1068.
Blank J., Koecher C., Pachinger W.H. et al. WO 2020230100 A1, 2020.
Dodd S.K., Furet P., Grotzfeld R.M. et al. PT WO 2013171639 A1, 2013.
Moore J.L., Taylor S.M., Soloshonok V.A. An efficient and operationally convenient general synthesis of tertiary amines by direct alkylation of secondary amines with alkyl halides in the presence of Huenig’s base. Arkivoc. 2005. 6(iv): 287–292.
doi.org/10.3998/ark.5550190.0006.624.
Cuadrado A., Manda G., Hassan A. et al. Transcription factor NRF2 as a therapeutic target for chronic diseases: a systems medicine approach. Pharmacolog. Rev. 2018. 70(2): 348–383.
doi.org/10.1124/pr.117.014753.
Saha S., Buttari B., Panieri E. et al. An Overview of Nrf2 Signaling Pathway and Its Role in Inflammation. Molecules. 2020. 25(22): 5474.
doi.org/10.3390/molecules25225474.
Borella R., Forti L., Gibellini L. et al. Synthesis and Anticancer Activity of CDDO and CDDO-Me, Two Derivatives of Natural Triterpenoids. Molecules. 2019. 24(22): 4097.
doi.org/10.3390/molecules24224097.
Shekh-Ahmad T., Eckel R., Dayalan Naidu S. et al. KEAP1 inhibition is neuroprotective and suppresses the development of epilepsy. Brain. 2018. 141(5): 1390–1403.
doi.org/10.1093/brain/awy071.
Sun H., Zhu J., Lin H. et al. Recent progress in the development of small molecule Nrf2 modulators: a patent review (2012-2016). Exp. Opin. Therap. Pat. 2017. 27(7): 763–785.
doi.org/10.1080/13543776.2017.1325464.
Profeta V., McIntyre K., Wells M. et al. Omaveloxolone: an activator of Nrf2 for the treatment of Friedreich ataxia. Exp. Opin. Investig. Drugs. 2023. 32(1): 5–16.
doi.org/10.1080/13543784.2023.2173063.
Anderson E., Decker A., Liu, X. PT WO 2013163344 A1, 2013.
Sporn M.B., Liby K.T., Yore M.M. et al. New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress. J. Nat. Prod. 2011. 74(3): 537–545.
doi.org/10.1021/np100826q.
Maddahi J., Lazewatsky J., Udelson J.E. et al. Phase-III clinical trial of fluorine-18 flurpiridaz positron emission tomography for evaluation of coronary artery disease. J. Am. Coll. Cardiol. 2020. 76(4): 391–401.
doi.org/10.1016/j.jacc.2020.05.063.
Berman D.S., Maddahi J., Tamarappoo B.K. et al. Phase II safety and clinical comparison with single-photon emission computed tomography myocardial perfusion imaging for detection of coronary artery disease: flurpiridaz F 18 positron emission tomography. J. Am. Coll. Cardiol. 2013. 61(4): 469–77.
https://doi.org/10.1016/j.jacc.2012.11.022.
Stendahl J.C., Kwan J.M., Pucar D., Sadeghi M.M. Radiotracers to address unmet clinical needs in cardiovascular imaging, part 1: technical considerations and perfusion and neuronal imaging. J. Nuc. Med. 2022. 63(5): 649–658.
doi.org/10.2967/jnumed.121.263506.
Patel K.K., Singh A., Bateman T.M. The potential of F-18 flurpiridaz PET/CT myocardial perfusion imaging for precision imaging. Curr. Cardiol. Rep. 2022. 24(8): 987–994.
doi.org/10.1007/s11886-022-01713-5.
Poitrasson-Rivière A., Moody J.B., Renaud J.M. et al. Impact of residual subtraction on myocardial blood flow and reserve estimates from rapid dynamic PET protocols. J. Nuc. Cardiol. 2022. 29(5): 2262–2270.
doi.org/10.1007/s12350-021-02837-x.
Wang Y., Lin Q., Shi H., Cheng D. Fluorine-18: radiochemistry and target-specific PET molecular probes design. Front. Chem. 2022. 10: 884517.
doi.org/10.3389/fchem.2022.884517.
Ahmed H., Haider A., Gisler L. et al. [18F] Flurpiridaz: Facile and Improved Precursor Synthesis for this Next‐Generation Cardiac Positron Emission Tomography Imaging Agent. ChemMedChem. 2020. 15(12): 1040–1043.
doi.org/10.1002/cmdc.202000085.
Yalamanchili P., Wexler E., Hayes M. et al. Mechanism of uptake and retention of F-18 BMS-747 158-02 in cardiomyocytes: a novel PET myocardial imaging agent. J. Nuc. Cardiol. 2007. 14: 782–788.
doi.org/10.1016/j.nuclcard.2007.07.009.
Purohit A., Radeke H., Azure M. et al. Synthesis and biological evaluation of pyridazinone analogues as potential cardiac positron emission tomography tracers. J. Med. Chem. 2008. 51(10): 2954–2970.
doi.org/10.1021/jm701443n.
Swamy K.K., Kumar N.B., Balaraman E., Kumar K.P. Mitsunobu and related reactions: advances and applications. Chem. Rev. 2009. 109(6): 2551–651.
doi.org/10.1021/cr800278z.
Suzuki H., Kawamura Y., Ogura T. et al. EP 0169375 B1, 1989.
Nelson T.D., Crouch R.D. Selective deprotection of silyl ethers. Synthesis. 1996. 9: 1031–1069.
doi: 10.1055/s-1996-4350.
Roeda D., Dolle F. Aliphatic Nucleophilic Radio-fluorination. Curr. Radiopharm. 2010. 3(2): 81–108.
doi.org/10.2174/1874471011003020081.
Vandebriel R., Cransveld C.C., Crommelin D. et al. Respiratory sensitization: Advances in assessing the risk of respiratory inflammation and irritation. Toxicol. In Vitro. 2011. 25(7): 1251–1258.
doi.org/10.1016/j.tiv.2011.04.027.
O’Kelley L., Swanson B., Bishop‐Royse J.C. Integrative literature review: Ethylene oxide exposure signs and symptoms. Pub. Health Nurs. 2023. 40(5): 790–809.
doi.org/10.1111/phn.13216.
Wishart N., Argiriadi M.A., Calderwood D.J. et al. WO2011068881, 2011.
Soloshonok V.A., Mikami K., Yamazaki T., Welch J.T., Honek J.F. Eds. Current fluoroorganic chemistry: new synthetic directions, technologies, materials, and biological applications. ACS Symposium Series #949; Oxford University Press, 2007.
doi: 10.1021/bk-2007-0949.
Burmester G.R., Kremer J.M., Van den Bosch F. et al. Safety and efficacy of upadacitinib in patients with rheumatoid arthritis and inadequate response to conventional synthetic disease-modifying anti-rheumatic drugs (SELECT-NEXT): a randomised, double-blind, placebo-controlled phase 3 trial. Lancet. 2018. 391(10139): 2503–2512.
doi: 10.1016/S0140-6736(18)31115-2.
Genovese M.C., Fleischmann R., Combe B. et al. Safety and efficacy of upadacitinib in patients with active rheumatoid arthritis refractory to biologic disease-modifying anti-rheumatic drugs (SELECT-BEYOND): a double-blind, randomised controlled phase 3 trial. Lancet. 2018. 391(10139): 2513–2524.
doi: 10.1016/S0140-6736(18)31116-4.
Smolen J.S., Pangan A.L., Emery P. et al. Upadacitinib as monotherapy in patients with active rheumatoid arthritis and inadequate response to methotrexate (SELECT-MONOTHERAPY): a randomised, placebo-controlled, double-blind phase 3 study. Lancet. 2019. 393(10188): 2303–2311.
doi: 10.1016/S0140-6736(19)30419-2.
Fleischmann R., Pangan A.L., Song I.H. et al. Upadacitinib versus placebo or adalimumab in patients with rheumatoid arthritis and an inadequate response to methotrexate: results of a phase III, double‐blind, randomized controlled trial. Arthritis Rheumatol. 2019. 71(11): 1788–800.
doi.org/10.1002/art.41032.
D’Amico F., Fiorino G., Furfaro F. et al. Janus kinase inhibitors for the treatment of inflammatory bowel diseases: developments from phase I and phase II clinical trials. Exp. Opin. Investig. Drugs. 2018. 27(7): 595–599.
org/10.1080/13543784.2018.1492547.
Pérez-Jeldres T., Tyler C.J., Boyer J.D. et al. Targeting cytokine signaling and lymphocyte traffic via small molecules in inflammatory bowel disease: JAK inhibitors and S1PR agonists. Front. Pharmacol. 2019. 10: 212.
doi.org/10.3389/fphar.2019.00212.
Ananthakrishnan A.N., Kaplan G.G., Bernstein C.N. et al. Lifestyle, behaviour, and environmental modification for the management of patients with inflammatory bowel diseases: an International Organization for Study of Inflammatory Bowel Diseases consensus. Lancet Gastroenterol. Hepatol. 2022. 7(7): 666–678.
doi: 10.1016/S2468-1253(22)00021-8.
Bakker D., de Bruin-Weller M., Drylewicz J. et al. Biomarkers in atopic dermatitis. J. Aller. Clin. Immunol. 2023. 151(5): 1163–1168.
https://doi.org/10.1016/j.jaci.2023.01.019.
Wishart N., Argiriadi M.A., Calderwood D.J. PCT/US2010/058572, 2011.
Voss J.W., Camp H.S., Padley R.J. PCT/US2014/062145, 2015.
Liu J., Han J., Izawa K. et al. Cyclic tailor-made amino acids in the design of modern pharmaceuticals. Eur. J. Med. Chem. 2020. 208: 112736. doi: 10.1016/j.ejmech.2020.112736.
Nakamura T., Tateishi K., Tsukagoshi S. et al. Self-disproportionation of enantiomers
of non-racemic chiral amine derivatives through achiral chromatography. Tetrahedron. 2012. 68(21): 4013–4017.
doi.org/10.1016/j.tet.2012.03.054.
Yasumoto M., Ueki H., Ono T. et al. Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro) lactate via sublimation: Sublimation rates vs. enantiomeric composition. J. Fluor. Chem. 2010. 131(4): 535–539.
doi.org/10.1016/j.jfluchem.2009.11.026.
Allian A., Jayanth J., Mohamed M.E. et al. PCT/US2016/057372, 2017.
Oruganti S., Kandagatla B., Sen S. et al. PCT/IB2018/055368, 2019.
Soloshonok V.A., Kirilenko A.G., Galushko S.V., Kukhar V.P. Catalytic asymmetric synthesis of β-fluoroalkyl-β-amino acids via biomimetic [1,3]-proton shift reaction. Tetrahedron Lett. 1994. 35(28): 5063–5064.
doi: 10.1016/S0040-4039(00)73320-X.
Soloshonok V.A., Ono T. The effect of substituents on the feasibility of azomethine-azomethine isomerization: New synthetic opportunities for biomimetic transamination. Tetrahedron. 1996. 52(47): 14701–14712.
doi: 10.1016/0040-4020(96)00920-9.
Soloshonok V.A., Yasumoto M. Catalytic asymmetric synthesis of α-(trifluoromethyl) benzylamine via cinchonidine derived base-catalyzed biomimetic 1,3-proton shift reaction. J. Fluor. Chem. 2007. 128(3): 170–173.
doi.org/10.1016/j.jfluchem.2006.11.011.
Ohkura H., Berbasov D.O., Soloshonok V.A. Chemo-and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds and amines. Improved synthesis of the corresponding imines/enamines. Tetrahedron. 2003. 59(10): 1647–1656.
doi.org/10.1016/S0040-4020(03)00138-8.
Soloshonok V.A., Ohkura H., Uneyama K. Biomimetic reductive amination of perfluoroalkylcarboxylic acids to α,α-dihydroperfluoroalkylamines. Tetrahedron Lett. 2002. 43(31): 5449–5452.
doi.org/10.1016/S0040-4039(02)01104-8.
Mospan C., Mospan G., Byland E. et al. Drug updates and approvals: 2018 in review. Nurse Pract. 2018. 43(12): 23–32.
doi: 10.1097/01.NPR.0000547548.63764.6b.
Donaldson S.H., Pilewski J.M., Griese M. et al. Tezacaftor/ivacaftor in subjects with cystic fibrosis and F508del/F508del-CFTR or F508del/G551D-CFTR. Am. J. Resp. Crit. Care Med. 2018. 197(2): 214–224.
doi.org/10.1164/rccm.201704-0717OC.
Zhang C., Chakma J. WO 2016/109362, 2016.
Furet P., Guagnano V., Fairhurst R.A. et al. Discovery of NVP-BYL719 a potent and selective phosphatidylinositol-3 kinase alpha inhibitor selected for clinical evaluation. Bioorg. Med. Chem. Lett. 2013. 23(13): 3741–3748.
doi.org/10.1016/j.bmcl.2013.05.007.
Gerspacher M., Fairhurst R.A., Mah R. et al. Discovery of a novel tricyclic 4H-thiazolo [5′,4′:4,5] pyrano[2,3-c]pyridine-2-amino scaffold and its application in a PI3Kα inhibitor with high PI3K isoform selectivity and potent cellular activity. Bioorg. Med. Chem. Lett. 2015. 25(17): 3582–3584.
doi.org/10.1016/j.bmcl.2015.06.077.
André F., Ciruelos E., Rubovszky G. et al. Alpelisib for PIK3CA-mutated, hormone receptor–positive advanced breast cancer. New Eng. J. Med. 2019. 380(20): 1929–1940.
doi: 10.1056/NEJMoa1813904.
Qiu W., Gu X., Soloshonok V.A. et al. Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics. Tetrahedron Lett. 2001. 42(2): 145–148.
doi: 10.1016/S0040-4039(00)01864-5.
Markham A. Alpelisib: first global approval. Drugs. 2019. 79(11): 1249–1253.
doi.org/10.1007/s40265-019-01161-6.
Singh R., Manjunatha U., Boshoff H.I. et al. PA-824 Kills Nonreplicating Mycobacterium tuberculosis by Intracellular NO Release. Science. 2008. 322(5906): 1392–1395.
doi: 10.1126/science.1164571.
Patterson S., Wyllie S., Stojanovski L. et al. The R enantiomer of the antitubercular drug PA-824 as a potential oral treatment for visceral Leishmaniasis. Antimic. Agents Chemother. 2013. 57(10): 4699–4706.
doi.org/10.1128/aac.00722-13.
Marsini M.A., Reider P.J., Sorensen E.J. A concise and convergent synthesis of PA-824. J. Org. Chem. 2010. 75(21): 7479–7482.
doi.org/10.1021/jo1015807.
Moraski G.C., Oliver A.G., Markley L.D. et al. Scaffold-switching: an exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine-3-carboxylates. Bioorg. Med. Chem. Lett. 2014. 24(15): 3493–3498.
doi.org/10.1016/j.bmcl.2014.05.062.
Keam S.J. Pretomanid: first approval. Drugs. 2019. 79(16): 1797–1803.
doi.org/10.1007/s40265-019-01207-9.
Baker W.R., Shaopei C., Keeler E.L. US 6087358, 2000.
Prelog V., Helmchen G. Basic principles of the CIP‐system and proposals for a revision. Angew. Chem., Int. Ed. 1982. 21(8): 567–583.
doi.org/10.1002/anie.198205671.
Klika K.D., Wzorek A., Soloshonok V.A. Internal chirality descriptors iR and iS and ire and isi. A proposed notation to extend the usefulness of the R/S system by retaining the sense of stereochemistry in cases of ligand ranking changes. Chirality. 2018. 30(9): 1054–1066.
doi: 10.1002/chir.22982.
Goadsby P.J., Edvinsson L., Ekman R. Vasoactive peptide release in the extracerebral circulation of humans during migraine headache. Ann. Neurol. 1990. 28(2): 183–187.
doi.org/10.1002/ana.410280213.
Bellamy J.L., Cady R.K., Durham P.L. Salivary levels of CGRP and VIP in rhinosinusitis and migraine patients. Headache: J. Head Face Pain. 2006. 46(1): 24–33.
doi.org/10.1111/j.1526-4610.2006.00294.x.
Lassen L.H., Haderslev P.A., Jacobsen V.B. et al. CGRP may play a causative role in migraine. Cephalalgia. 2002. 22(1): 54–61.
doi.org/10.1046/j.1468–2982.2002.00310.x.
Olesen J., Diener H., Husstedt I.W. et al. Calcitonin gene-related peptide receptor antagonist BIBN4096BSfor the acute treatment of migraine. New Eng. J. Med. 2004. 350(11): 1104–1111
doi.org/10.1007/s00415-017-8434-y10.
Petersen K.A., Lassen L.H., Birk S. et al. BIBN4096BS Antagonizes Human α‐calcitonin Gene Related Peptide-induced Headache and Extracerebral Artery Dilatation. Clin. Pharmacol. Therap. 2005. 77(3): 202–213.
doi.org/10.1016/j.clpt.2004.10.001.
Doods H., Hallermayer G., Wu D. et al. Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist. Brit. J. Pharmacol. 2000. 129(3): 420–423.
doi.org/10.1038/sj.bjp.0703110.
Edvinsson L., Goadsby P.J. Neuropeptides in migraine and cluster headache. Cephalalgia. 1994.14(5): 320-327.
doi.org/10.1046/j.1468–2982.1994.14053 20.x.
Ashina M., Bendtsen L., Jensen R. et al. Plasma levels of calcitonin gene-related peptide in chronic tension-type headache. Neurology. 2000. 55(9): 1335–1340.
doi.org/10.1212/WNL.55.9.1335.
Holzer P. Local effector function of capsaicin gene-related peptide and other neuropeptides. Neuroscience. 1998. 24: 739–768.
doi.org/10.1111/j.1440-1681.1996.tb02579.x.
Salmon A.M., Damaj M.I., Marubio L.M. et al. Altered neuroadaptation in opiate dependence and neurogenic inflammatory nociception in αCGRP-deficient mice. Nat. Neurosci. 2001. 4(4): 357–358.
doi.org/10.1038/86001.
May A., Gamulescu M.A., Bogdahn U., Lohmann C.P. Intractable eye pain: indication for triptans. Cephalalgia. 2002. 22(3): 195–196.
doi.org/10.1046/j.1468-2982.2002.00342.x.
«Asymmetric Synthesis and Application of alpha-Amino Acids.” ACS Symposium Series #1009; Soloshonok V.A., Izawa K. Eds., Oxford University Press, 2009.
doi: 10.1021/bk-2009-1009.
Fluorine-Containing Amino Acids. Synthesis and Properties, Kukhar V.P., Soloshonok V.A. Eds., John Wiley & Sons Ltd., 1994. ISBN-10: 0471952036.
Wang Y., Song X., Wang J. et al. Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes. Amino Acids. 2017. 49(9): 1487–1520.
doi: 10.1007/s00726-017-2458-6.
Chen F., Molinaro C., Wuelfing W.P. et al. WO2013169348, 2013.
Bell I.M., Fraley M.E., Gallicchio S.N. et al. WO2012064910A1, 2012.
Takeda R., Kawamura A., Kawashima A. et al. Chemical dynamic kinetic resolution and S/R interconversion of unprotected α‐amino acids. Angew. Chem., Int. Ed. 2014. 53(45): 12214–12217.
doi.org/10.1002/anie.201407944.
Nian Y., Wang J., Zhou S. et al. Recyclable ligands for the non‐enzymatic dynamic kinetic resolution of challenging α‐amino acids. Angew. Chem., Int. Ed. 2015. 54(44): 12918–12922.
doi.org/10.1002/anie.201507273.
Sorochinsky A.E., Ueki H., Aceña J.L. et al. Chemical approach for interconversion of (S)-and (R)-α-amino acids. Org. Biomol. Chem. 2013. 11(27): 4503–4507.
doi:10.1039/C3OB40541A.
Zou Y., Han J., Saghyan A.S. et al. Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature. Molecules. 2020. 25(12): 2739.
doi.org/10.3390/molecules25122739.
Han J., Sorochinsky A.E., Ono T., Soloshonok V.A. Biomimetic Transamination – a Metal-Free Alternative to the Reductive Amination. Application for Generalized Preparation of Fluorine-Containing Amines and Amino Acids. Curr. Org. Syn. 2011. 8(2): 281–294.
doi.org/10.2174/157017911794697277.
Soloshonok V.A., Sorochinsky A.E. Practical methods for the synthesis of symmetrically α,α-disubstituted α-amino acids. Synthesis. 2010. 14: 2319–2344.
doi: 10.1055/s-0029-1220013.
De Camp W.H. Chiral drugs: The FDA perspective on manufacturing and control. J. Pharm. Biomed. Anal. 1993. 11(11–12): 1167–1172.
doi.org/10.1016/0731-7085(93)80100-F.
Daniels J.M., Nestmann E.R., Kerr A. Development of stereoisomers (chiral) drugs: A brief review of scientific and regulatory considerations. Drug Inf. J. 1997. 31(3): 639–646.
doi.org/10.1177/009286159703100303.
De Camp W.H. The FDA perspective on the development of stereoisomers. Chirality. 1989. 1(1): 2–6.
doi.org/10.1002/chir.530010103.
Soloshonok V.A. Remarkable amplification of the self‐disproportionation of enantiomers on achiral‐phase chromatography columns. Angew. Chem., Int. Ed. 2006. 45(5): 766–769.
doi.org/10.1002/anie.200503373.
Soloshonok V.A., Ueki H., Yasumoto M. et al. Phenomenon of optical self-purification of chiral non-racemic compounds. J. Am. Chem. Soc. 2007. 129(40): 12112–12113.
doi: 10.1021/ja065603a.
Soloshonok V.A., Klika K.D. Terminology related to the phenomenon ‘self-disproportionation of enantiomers’ (SDE). Helv. Chem. Acta. 2014, 97(11): 1583–1589.
doi: 10.1002/hlca.201400122.
Ueki H., Yasumoto M., Soloshonok V.A. Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications. Tetrahedron: Asymmetry. 2010. 21(11–12): 1396–1400.
doi: 10.1016/j.tetasy.2010.04.040.
Sorochinsky A.E., Katagiri T., Ono T. et al. Optical purifications via self-disproportionation of enantiomers by achiral chromatography; Case study of a series of α-CF3-containing secondary alcohols. Chirality. 2013. 25(6): 365–368.
doi: 10.1002/chir.22180.
Sorochinsky A.E., Aceña J.L., Soloshonok V.A. Self-disproportionation of enantiomers of chiral, non-racemic fluoroorganic compounds: Role of fluorine as enabling element. Synthesis. 2013. 45(2): 141–152.
doi: 10.1055/s-0032-1316812.
Han J., Wzorek A., Kwiatkowska M. et al. The self-disproportionation of enantiomers (SDE) of amino acids and their derivatives. Amino Acids. 2019. 51(6): 865–889.
doi: 10.1007/s00726-019-02729-y.
Wzorek A., Sato A., Drabowicz J. et al. Remarkable magnitude of the self-disproportionation of enantiomers (SDE) via achiral chromatography; application to the practical-scale enantiopurification of β-amino acid esters. Amino Acids. 2016. 48(2): 605–613.
doi: 10.1007/s00726-015-2152-5.
Hosaka T., Imai T., Wzorek A. et al. The self-disproportionation of enantiomers (SDE) of α-amino acid derivatives; facets of steric and electronic properties. Amino Acids. 2019. 51(2): 283–294.
doi: 10.1007/s00726-018-2664-x.
Soloshonok V.A., Wzorek A., Klika K.D. A question of policy: should tests for the self-disproportionation of enantiomers (SDE) be mandatory for reports involving scalemates? Tetrahedron: Asymmetry. 2017. 28(10): 1430–1434.
doi: 10.1016/j.tetasy.2017.08.020.
Han J., Soloshonok V.A., Klika K.D. et al. Chiral sulfoxides: advances in asymmetric synthesis and problems with the accurate determination of the stereochemical outcome. Chem. Soc. Rev. 2018. 47(4): 1307–1350.
doi: 10.1039/c6cs00703a.
Soloshonok V.A., Roussel C., Kitagawa O., Sorochinsky A.E. Self-disproportionation of enantiomers via achiral chromatography: a warning and extra dimension in optical purifications. Chem. Soc. Rev. 2012. 41(11): 4180–4188.
doi:10.1039/C2CS35006H.
Han J., Kitagawa O., Wzorek A. et al. The self-disproportionation of enantiomers (SDE): a menace or an opportunity? Chem. Sci. 2018. 9(7): 1718–1739.
doi: 10.1039/C7SC05138G.
Han J., Dembinski R., Soloshonok V.A., Klika K.D. A call for a change in policy regarding the necessity for SDE tests to validate the veracity of the outcome of enantioselective syntheses, the inherent chiral state of natural products, and other cases involving enantioenriched samples. Molecules. 2021. 26(13): 3994.
doi.org/10.3390/molecules26133994.
Han J., Wzorek A., Klika K.D., Soloshonok V.A. Recommended tests for the self-disproportionation of enantiomers (SDE) to ensure accurate reporting of the stereochemical outcome of enantioselective reactions. Molecules. 2021. 26(9): 2757.
doi.org/10.3390/molecules26092757.
Yasumoto M., Ueki H., Soloshonok V.A. Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation. J. Fluor. Chem. 2010. 131(2): 266–269.
doi.org/10.1016/j.jfluchem.2009.10.002.
Albrecht M., Soloshonok V.A., Schrader L. et al. Chirality-dependent sublimation of α-(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers. J. Fluor. Chem. 2010. 131(4): 495–504.
doi.org/10.1016/j.jfluchem.2009.11.015.
Yasumoto M., Ueki H., Soloshonok V.A. Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation. J. Fluor. Chem. 2010. 131(4): 540–544.
doi.org/10.1016/j.jfluchem.2009.11.010.
Han J., Kiss L., Mei H. et al. Chemical aspects of human and environmental overload with fluorine. Chem. Rev. 2021. 121(8): 4678–4742.
doi.org/10.1021/acs.chemrev.0c01263.
Kanduti D., Sterbenk P., Artnik B. Fluoride: a review of use and effects on health. Materia Socio-Med. 2016. 28(2): 133.
doi: 10.5455/msm.2016.28.133-137.
Zuo H., Chen L., Kong M. et al. Toxic effects of fluoride on organisms. Life Sci. 2018. 198: 18–24. doi.org/10.1016/j.lfs.2018.02.001.
Ghosh A., Mukherjee K., Ghosh S.K., Saha B. Sources and toxicity of fluoride in the environment. Res. Chem. Intermed. 2013. 39: 2881–2915.
doi.org/10.1007/s11164-012-0841-1.
Holaday D.A., Fiserova-Bergerova V. Fate of fluorinated metabolites of inhalation anesthetics in man. Drug Metab. Rev. 1979. 9(1): 61–78.
doi.org/10.3109/03602537909046434.
Jeschke P. Current trends in the design of fluorine‐containing agrochemicals. In: Organofluorine chemistry: Synthesis, modeling, and applications. Szabó K., Selander N. Eds., 2021. 363–395.
doi.org/10.1002/9783527825158.ch11.
Brunn H., Arnold G., Körner W. et al. PFAS: forever chemicals—persistent, bioaccumulative and mobile. Reviewing the status and the need for their phase out and remediation of contaminated sites. Environ. Sci. Eur. 2023. 35(1): 1–50.
doi.org/10.1186/s12302-023-00721-8.
Han J., Wzorek A., Klika K.D. et al. Bioavailable Plastic: From Cognitive Decline in the Old to Hormonal Disruption in the Young. Ukr. Chem. J., 2025, 91(5), 33-62.
doi: 10.33609/2708-129X.91.5.2025.33-62.