α-Carboxylate phosphabetains in alkylation and complexation reactions

S.R. Romanov ^a*, K.O. Shibaeva ^a**, R.R. Minnullin ^a***, M.P. Shulaeva ^b****,

O.K. Pozdeev ^b*****, A.S. Tapalova ^c******, I.V. Galkina ^a*******, Yu.V. Bakhtiyarova ^a********

^aKazan Federal University, Kazan, 420008 Russia

^bKazan State Medical Academy, Kazan, 420012 Russia

^cKorkyt Ata Kyzylorda University, Kyzylorda, 120014 Kazakhstan

E-mail: ^*semyonromanov@yandex.ru, ^**shikaol@yandex.ru,

^***alkhimik-royal@mail.ru, ^****shulaeva.m@mail.ru, ^*****pozdeevoscar@rambler.ru,

^******anipa52@mail.ru, ^*******vig54@mail.ru, ^********Julbakh@mail.ru

Received December 4, 2022; Accepted January 18, 2023

ORIGINAL ARTICLE

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DOI: 10.26907/2542-064X.2023.1.158-169

For citation: 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, vol. 165, no. 1, pp. 158–169. doi: 10.26907/2542-064X.2023.1.158-169. (In Russian)

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

Acknowledgments. This study was supported by the Kazan Federal University Strategic Academic Leadership Program (PRIORITY-2030).

Figure Captions

Fig. 1. Molecular structure of compound 12.

Scheme 1. Synthesis of carboxylate phosphabetaines based on glyoxylic acid.

Scheme 2. Alkylation of monocarboxylate phosphabetaines.

Scheme 3. Alkylation of dicarboxylate phosphabetaines.

Scheme 4. Alkylation of carboxylate betaine 1 under mild conditions.

Scheme 5. Reactions of phosphabetaine complexation 3.

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