Анотація
Досліджено процеси комплексоутворення N-алілтіоамідів піримідиніл(циклогексеніл)карбонових кислот (H2L1–H2L3), а також продуктів їх протоно- та йодоциклізації HL4, HL5 з іонами Zn(II) і Ag(I). Показано, що виділені в твердому стані комплексні сполуки Zn(II) та Ag(I) з карботіоамідами H2L1–H2L3 відповідають співвідношенню компонентів M:L = 1:1 і 1:2, натомість продукти протоно- та йодоциклізації алілзаміщених тіоамідів HL4, HL5 утворюють комплекси тільки у співвідношеннях M:L = 1:2. Методами ІЧ, ЕСП та спектроскопії ЯМР 1Н встановлено спосіб координації лігандів і місце локалізації координаційного зв’язку.
Посилання
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5. Chen J., Fukuzumi K., Ip B., Florence, Cid A.P. Metal Coordination chemistry in the study of biological pathway and processes: A review. // Inter. J. Pharm. Biol. Chem. Sci. 2014. 3 (3): 36−45.
6. Dilworth J.R., Hueting R. Metal complexes of thiosemicarbazones for imaging and therapy. Inorg. Chim. Acta. 2012. 389: 3−15.
7. Pelosi G. Thiosemicarbazone metal complexes: From structure to activity // The Open Crystallography Journal. 2010. 3, (2): 16−28.
8. Koch K.R. New chemistry with old ligands: N-alkyl- and N,N-dialkyl-N-acyl(aroyl)thioureas in co-ordination, analytical and process chemistry of the platinum group metals. Coord. Chem. Rev. 2001. 216–217: 473−488.
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10. Orysyk S.I., Bon V.V., Zholob O.O., Pekhnyo V.I., Orysyk V.V., Zborovskii Yu.L., Vovk M.V. Novel Pd(II) coordination compounds involving 2-[(2-hydroxyphenyl)methylene]hydrazine-N-(2-propenyl)-carbothioamide as a ligand or pro-ligand: Synthesis, crystal structures and analytical application. Polyhedron. 2013. 51: 211−221.
11. Dey P., Basu S. Liquid–liquid extraction of silver(I) with 2-hydroxy-1-naphthaldehyde thiosemicarbazone into cyclohexene from nitrate medium in presence of neutral oxygen donor compounds. Internat. J. ChemTech Res. 2011. 3 (3): 1349−1358.
12. Banerjee S. Basu S. Synergistic extraction of Th(IV) by 2-hydroxy-1-naphthaldehyde thiosemicarbazone and neutral donors. Radiochim. Acta. 2003. 91 (2): 97−103.
13. Hossain Md.S., Roy P.K., Ali R., Zakaria C.M., Kudrat-E-Zahan Md. Selected pharmacological applications of 1st row transition metal complexes: A review. Clinical Med. Res. 2017. 6 (6): 177−191.
14. Zhao Y., Wang L., Guo C., Jiang B., Li X., Liu K., Shi D. Metal complexes of thiosemicarbazones as potent anticancer agents: a minireview. Med. Res. 2018. 2 (2). 20180009; doi: 10.21127/yaoyimr20180009.
15. Hossain Md.S., Zakaria C.M., Kudrat-E-Zahan Md. Metal complexes as potential antimicrobial agent: A review. Amer. J. Heterocycl. Chem. 2018. 4 (1): P. 1−21.
16. Patra M. Gasser G. Organometallic compounds: An opportunity for chemical biology? ChemBioChem. 2012. 13 (9): 1232−1252.
17. Zelenin K.N., Khorseeva L.A., Toshev M.T., Alekseev V.V., Dustov Kh.B. Zh. Obshch. Khim. 1990 (Russ.). Russ. J. Gen. Chem. 1990. 60: 2549.
18. Orysyk S.I., Bon V.V., Obolentseva O.V., Zborovskii Yu.L., Orysyk V.V., Pekhnyo V.I., Staninets V.I., Vovk M.V. Synthesis, structural and spectral characterization of Zn(II) complexes, derived from thiourea and thiosemicarbazide. Inorg. Chim. Acta. 2012. 382: 127−138.
19. Orysyk S.I., Bon V.V., Pekhnyo V.I., Zborovskii Yu.L., Orysyk V.V., Vovk M.V. Synthesis, structure and spectral characteristics of Ni(II), Pd(II) and Zn(II) complexes with N-(2-pyridinyl)morpholine-4-carbothioamide. Polyhedron. 2012. 38: Р.15–25.
20. Repich H.H. Synthesis, structure and spectral characteristics of Fe(III), Co(II), Ni(II), Cu(II), Pd(II), Pt(II), Ag(I) with thiourea, hydrazone and thiosemicarbazone derivatives. Ph.D (Chem.) Thesis. (Kyiv, 2015). С.108−120 http://www.ionc.kiev.ua/ssc/2016/GRepich_thesis.pdf
21. Klimova V.A. The main micro methods of analysis of organic compounds. (Moscow: Chemistry, 1967). 19−55, 101−107.
22. Wesolowska A., Jagodziñski T.S., Sosnicki J.G., Hansen P.E. Synthesis of the N-Allylthioamide Derivatives of Cyclic Oxo- and Dioxo- Acids and Their Cyclization to the Derivatives of 4,5-Dihydrothiazole. Polish J. Chem. 2001. 75: 387−400.
23. Hansen P.E., Duus F., Bolvig S., Jagodzinski T.S. Intramolecular hydrogen bonding of the enol forms of β-ketoamides and β-ketothioamides. Deuterium isotope effects on 13C chemical shifts. Journal of Molecular Structure. 1996. 378: 45−59.
24. Litvinchuk M.B., Bentya А.V., Slyvka N.Yu., Vovk М.V. 5-Functionalized (1,3-thiazolidine-2-ylidene)pirymidin-2,4,6-tri¬ones. Ukr. Chim. Zhurn. 2017. 83 (10): 90−99.
2. Frija L.M.T., Pombeiro A.J.L., Kopylovich M.N. Coordination chemistry of thiazoles, isothiazoles and thiadiazoles. Coord. Chem. Rev. 2016. 308, Pt. 1: 32−55.
3. Haas K.L., Franz. K.J. Application of metal coordination chemistry to explore and manipulate cell biology. Chem. Rev. 2009. 109 (10): 4921−4960.
4. Bhasin H., Bhatt V. The state of art in coordination compounds with antifungal activity. J. Chem. and Chem. Sci. 2018. 8 (3): 595−605.
5. Chen J., Fukuzumi K., Ip B., Florence, Cid A.P. Metal Coordination chemistry in the study of biological pathway and processes: A review. // Inter. J. Pharm. Biol. Chem. Sci. 2014. 3 (3): 36−45.
6. Dilworth J.R., Hueting R. Metal complexes of thiosemicarbazones for imaging and therapy. Inorg. Chim. Acta. 2012. 389: 3−15.
7. Pelosi G. Thiosemicarbazone metal complexes: From structure to activity // The Open Crystallography Journal. 2010. 3, (2): 16−28.
8. Koch K.R. New chemistry with old ligands: N-alkyl- and N,N-dialkyl-N-acyl(aroyl)thioureas in co-ordination, analytical and process chemistry of the platinum group metals. Coord. Chem. Rev. 2001. 216–217: 473−488.
9. Singh R.B., lshii H. Analytical potentialities of thiosemicarbazones and semicarbazones. Critical Rev. Analyt. Chem. 1991. 22 (5): 381−409.
10. Orysyk S.I., Bon V.V., Zholob O.O., Pekhnyo V.I., Orysyk V.V., Zborovskii Yu.L., Vovk M.V. Novel Pd(II) coordination compounds involving 2-[(2-hydroxyphenyl)methylene]hydrazine-N-(2-propenyl)-carbothioamide as a ligand or pro-ligand: Synthesis, crystal structures and analytical application. Polyhedron. 2013. 51: 211−221.
11. Dey P., Basu S. Liquid–liquid extraction of silver(I) with 2-hydroxy-1-naphthaldehyde thiosemicarbazone into cyclohexene from nitrate medium in presence of neutral oxygen donor compounds. Internat. J. ChemTech Res. 2011. 3 (3): 1349−1358.
12. Banerjee S. Basu S. Synergistic extraction of Th(IV) by 2-hydroxy-1-naphthaldehyde thiosemicarbazone and neutral donors. Radiochim. Acta. 2003. 91 (2): 97−103.
13. Hossain Md.S., Roy P.K., Ali R., Zakaria C.M., Kudrat-E-Zahan Md. Selected pharmacological applications of 1st row transition metal complexes: A review. Clinical Med. Res. 2017. 6 (6): 177−191.
14. Zhao Y., Wang L., Guo C., Jiang B., Li X., Liu K., Shi D. Metal complexes of thiosemicarbazones as potent anticancer agents: a minireview. Med. Res. 2018. 2 (2). 20180009; doi: 10.21127/yaoyimr20180009.
15. Hossain Md.S., Zakaria C.M., Kudrat-E-Zahan Md. Metal complexes as potential antimicrobial agent: A review. Amer. J. Heterocycl. Chem. 2018. 4 (1): P. 1−21.
16. Patra M. Gasser G. Organometallic compounds: An opportunity for chemical biology? ChemBioChem. 2012. 13 (9): 1232−1252.
17. Zelenin K.N., Khorseeva L.A., Toshev M.T., Alekseev V.V., Dustov Kh.B. Zh. Obshch. Khim. 1990 (Russ.). Russ. J. Gen. Chem. 1990. 60: 2549.
18. Orysyk S.I., Bon V.V., Obolentseva O.V., Zborovskii Yu.L., Orysyk V.V., Pekhnyo V.I., Staninets V.I., Vovk M.V. Synthesis, structural and spectral characterization of Zn(II) complexes, derived from thiourea and thiosemicarbazide. Inorg. Chim. Acta. 2012. 382: 127−138.
19. Orysyk S.I., Bon V.V., Pekhnyo V.I., Zborovskii Yu.L., Orysyk V.V., Vovk M.V. Synthesis, structure and spectral characteristics of Ni(II), Pd(II) and Zn(II) complexes with N-(2-pyridinyl)morpholine-4-carbothioamide. Polyhedron. 2012. 38: Р.15–25.
20. Repich H.H. Synthesis, structure and spectral characteristics of Fe(III), Co(II), Ni(II), Cu(II), Pd(II), Pt(II), Ag(I) with thiourea, hydrazone and thiosemicarbazone derivatives. Ph.D (Chem.) Thesis. (Kyiv, 2015). С.108−120 http://www.ionc.kiev.ua/ssc/2016/GRepich_thesis.pdf
21. Klimova V.A. The main micro methods of analysis of organic compounds. (Moscow: Chemistry, 1967). 19−55, 101−107.
22. Wesolowska A., Jagodziñski T.S., Sosnicki J.G., Hansen P.E. Synthesis of the N-Allylthioamide Derivatives of Cyclic Oxo- and Dioxo- Acids and Their Cyclization to the Derivatives of 4,5-Dihydrothiazole. Polish J. Chem. 2001. 75: 387−400.
23. Hansen P.E., Duus F., Bolvig S., Jagodzinski T.S. Intramolecular hydrogen bonding of the enol forms of β-ketoamides and β-ketothioamides. Deuterium isotope effects on 13C chemical shifts. Journal of Molecular Structure. 1996. 378: 45−59.
24. Litvinchuk M.B., Bentya А.V., Slyvka N.Yu., Vovk М.V. 5-Functionalized (1,3-thiazolidine-2-ylidene)pirymidin-2,4,6-tri¬ones. Ukr. Chim. Zhurn. 2017. 83 (10): 90−99.
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Авторське право (c) 2019 Polina Borovyk, Mariia Litvinchuk, Anton Bentya, Svitlana Orysyk, Yurii Zborovskiy, Nataliia Slyvka
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