α-Carboxylate Phosphabetains in Alkylation and Complexation Reactions
https://doi.org/10.26907/2542-064X.2023.1.158-169
Abstract
Alkylation reactions of α-carboxylate phosphabetaines were carried out and studied to enhance the biological activity of previously synthesized carboxylate phosphabetaines. As a result of these reactions, the original structure was destroyed with the formation of quaternary salts of phosphonium triiodide. The structure and composition were confirmed by a complex of physical research methods, including NMR, IR spectroscopy, and elemental analysis. The bactericidal and antimycotic activity of the synthesized salts was assessed. The compounds showed activity similar to that of commercial drugs. The reactions of complexation of these structures were also investigated. In the reactions with nickel and copper chloride, complexes were isolated and characterized. The structure of the nickel complex was unambiguously confirmed by the data obtained with the help of single-crystal X-ray diffraction analysis.
Keywords
glyoxylic acid,
tertiary phosphine,
phosphabetaine,
alkylation,
methyl iodide,
antimicrobial activity
Supporting agencies: This study was supported by the Kazan Federal University Strategic Academic Leadership Program (PRIORITY-2030).
About the Authors
S. R. Romanov
Kazan Federal University
Russian Federation
Russian Federation
Kazan, 420008
K. O. Shibaeva
Kazan Federal University
Russian Federation
Russian Federation
Kazan, 420008
R. R. Minnullin
Kazan Federal University
Russian Federation
Russian Federation
Kazan, 420008
M. P. Shulaeva
Kazan State Medical Academy
Russian Federation
Russian Federation
Kazan, 420012
O. K. Pozdeev
Kazan State Medical Academy
Russian Federation
Russian Federation
Kazan, 420012
A. S. Tapalova
Korkyt Ata Kyzylorda University
Kazakhstan
Kazakhstan
Kyzylorda, 120014
I. V. Galkina
Kazan Federal University
Russian Federation
Russian Federation
Kazan, 420008
Yu. V. Bakhtiyarova
Kazan Federal University
Russian Federation
Russian Federation
Kazan, 420008
References
1. Huang X., Weiss R.G. Silica structures templated on fibers of tetraalkylphosphonium salt gelators in organogels // Langmuir. – 2006. – V. 22, No 20. – P. 8542–8552. – doi: la0610250.s001.
2. Pomecko R., Asfari Z., HubscherBruder V., Bochenska M., Arnaud Neu F. Anion recognition by phosphonium calix[4]arenes: Synthesis and physico-chemical studies // Supramol. Chem. – 2010. – V. 22, No 5. – P. 275–288. – doi: 10.1080/10610270903437051.
3. Kanazava A., Ikeda T., Endo T. Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths // Antimicrob. Agents Chemother. – 1994. – V. 38, No 5. – P. 945–952. – doi: 10.1128/AAC.38.5.945.
4. Mollahosseini A., Abdelrasoul A., Shoker A. Latest advances in zwitterionic structures modified dialysis membranes // Mater. Today Chem. – 2020. – V. 15. – Art. 100227. – doi: 10.1016/j.mtchem.2019.100227.
5. Xu D., We H., Zhen Y., Gao Y.-Q., Li R., Li X., He Y., Zhang Zh., Xie W. Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane // Org. Chem. Front. – 2019. – V. 6. – P. 1681–1685. – doi: 10.1039/C9QO00304E.
6. Zhou H., Wang G.-H., Zhang W.-Zh., Lu X.-B. CO2 adducts of phosphorus ylides: Highly active organocatalysts for carbon dioxide transformation // ACS Catal. – 2015. – V. 5, No 11. – P. 6773–6779. – doi: 10.1021/acscatal.5b01409.
7. Galkina I., Tufatullin A., Krivolapov D., Bakhtiyarova Yu., Chubukaeva D., Stakheev V., Galkin V., Cherkasov R., Büchner B., Kataeva O. Crystal structure of phosphonium carboxylate complexes. The role of the metal coordination geometry, ligand conformation and hydrogen bonding // CrystEngComm. – 2014. – V. 16, No 38. – P. 9010–9024. – doi: 10.1039/c4ce01361a.
8. Bakhtiyarova Yu.V., Morozov M.V., Romanov S.R., Minnullin R.R., Shulaeva M.P., Pozdeev O.K., Galkin V.I. New biologically active phosphonium salts based on 3-(diphenylphosphino)propionic acid and unsaturated amides // Russ. Chem. Bull. – 2020. – V. 69, No 8. – P. 1569–1572. – doi: 10.1007/s11172-020-2936-y.
9. Romanov S.R., Dolgova Y.V., Morozov M.V., Ivshin K.A., Semenov D.A., Bakhtiyarova Yu.V., Galkina I.V., Galkin V.I. New phosphonium salts based on 3-(diphenylphosphino)propanoic and ω-haloalkanoic acids // Mendeleev Commun. – 2021. – V. 31, No 31. – P. 242–243. – doi: 10.1016/j.mencom.2021.03.032.
10. Romanov S.R., Aksunova A.F., Islamov D.R., Dobrynin A.B., Krivolapov D.B., Kataeva O.N., Bakhtiyarova Yu.V., Galkina I.V., Galkin V.I. Triphenylphosphine in reactions with ωhaloalkylcarboxylic acid // Phosphorus, Sulfur, Silicon Relat. Elem. – 2016. – V. 191, No 11–12. – P. 1637–1639. – doi: 10.1080/10426507.2016.1223661v.
11. Galkin V.I., Bakhtiyarova Yu.V., Polezhaeva N.A., Cherkasov R.A., Krivolapov D.B., Gubaidullin A.T., Litvinov I.A. Synthesis, structure and reactivity of carboxylate phosphabetaines // Phosphorus, Sulfur, Silicon Relat. Elem. – 1999. – V. 147, No 1. – P. 91. – doi: 10.1080/10426509908053526.
12. Bakhtiyarova Yu.V., Aksunova A.F., Romanov S.R., Bakhtiyarov D.I., Ivshin K.A., Kataeva O.N., Egorova S.N., Galkina I.V., Galkin V.I. The reaction of phosphorylation of trans-aconitic acid by tertiary phosphines // Phosphorus, Sulfur, Silicon Relat. Elem. - 2019. – V. 194, No 4–6. – P. 319–320. – doi: 10.1080/10426507.2018.1539999.
13. Riddick J.A., Bunger W.B., Sakano T.K. Organic Solvents: Physical Properties and Methods of Purification. – N. Y.: Wiley-Interscience, 1986. – 1344 р.
14. Armarego W.L.F., Chai C.L.L. Purification of Laboratory Chemicals. – Burlington: Butterworth–Heinemann, 2009. – 743 p.
15. Kormachev V.V., Fedoseev M.S. Preparativnaya khimiya fosfora [Preparative Chemistry of Phosphorus]. Perm, Ural. Otd. Ross. Akad. Nauk, 1992. 458 p. (In Russian)
16. Galkina I.V., Romanov S.R., Gerasimov A.V., Bakhtiyarova Yu.V., Galkin V.I. Synthesis of stable carboxylate phosphabetaines – Potential ligands of the metal complexes // J. Organomet. Chem. – 2020. – V. 910. – Art. 121131. – doi: 10.1016/j.jorganchem.2020.121131.
17. Mazurkiewicz R., Październiok-Holewa A., Grymel M. N-acyl-α-triphenylphosphonio-αamino acids: Synthesis and decarboxylation to α-(N-acylamino)alkyltriphenylphosphonium salts // Phosphorus, Sulfur, Silicon Relat. Elem. – 2009. – V. 184, No 4. – P. 1017–1027. – doi: 10.1016/j.tetlet.2008.01.051.
18. Basvani K., Fomina O., Yakhfarov D., Heinicke J. Synthesis and properties of zwitterionic phosphonioglycolates // Polyhedron. – 2014. – V. 67 – P. 306–313. – doi: 10.1016/j.poly.2013.09.016.
19. Davison J.C., Foreman M.R., Howie R.A., Plater M.J., Skakle J.M. A new polymorph, form C, of [1,2-bis(diphenylphosphino)ethane]-dichloronickel(II) // Acta Crystallogr., Sect. C: Struct. Chem. – 2001. – V. 57, Pt. 6. – P. 690–693. – doi: 10.1107/s0108270101003961
Review
For citations:
Romanov S.R., Shibaeva K.O., Minnullin R.R., Shulaeva M.P., Pozdeev O.K., Tapalova A.S., Galkina I.V., Bakhtiyarova Yu.V. α-Carboxylate Phosphabetains in Alkylation and Complexation Reactions. Uchenye Zapiski Kazanskogo Universiteta Seriya Estestvennye Nauki. 2023;165(1):158–169. (In Russ.) https://doi.org/10.26907/2542-064X.2023.1.158-169
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