SYNTHESIS, ANTIMICROBIAL ACTIVITY, AND MOLECULAR DOCKING OF N-PHENYLCARBAMATE DERIVATIVES WITH A HETEROCYCLIC MOIETY

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Abstract

By condensing o-phenylenediamine with 2(4)-aminobenzoic acids in 65% polyphosphoric acid at a temperature of 180–190°C for 4 h or by boiling the reagents in o-xylene in the presence of tetrabutoxytitanium, 2-(2(4)-aminophenyl)benzimidazoles were obtained, the acylation of which with methyl chloroformate in the presence of triethylamine led to the production of the corresponding benzimidazoles with a carbamate function. Condensation of o-phenylenediamine and 4-nitro-o-phenylenediamine with glycolic acid in the presence of 70–75% polyphosphoric acid with heating for four hours at 130°C yielded 2-hydroxymethylbenzimidazole with a yield of 81% and 5-nitro-2-hydroxymethylbenzimidazole with a yield of 84%, which, when treated with phenyl isocyanate in tetrahydrofuran at 27–30°C for 3.5 h, were converted into the corresponding benzimidazole derivatives with a yield of 84–86%. In order to find the most promising ones for further biological research, molecular docking of synthesized 2-substituted benzimidazoles, as well as previously obtained carbamate derivatives of pyridazine and N-allyl derivatives of 2-morpholinoethyl-N-phenylcarbamate and 2-(2-pyridinyl)ethyl-N-phenylcarbamate was carried out based on interaction with the enzyme glucosamine-6-phosphate synthase.

About the authors

A. V. Velikorodov

Tatishchev Astrakhan State University,; Astrakhan State Medical University, Ministry of Health of the Russian Federation,

Email: avelikorodov@mail.ru
Russia, 414000 Astrakhan, pl. Shaumyana, 1; Russia, 414000 Astrakhan, ul. Bakinskaya, 121

S. V. Borisova

Razumovsky Saratov State Medical University, Ministry of Health of the Russian Federation,

Russia, 410012 Saratov, ul. Bolshaya Kazachia, 112

E. A. Shustova

Astrakhan State Medical University, Ministry of Health of the Russian Federation,

Russia, 414000 Astrakhan, ul. Bakinskaya, 121

E. N. Kutlalieva

Tatishchev Astrakhan State University,; Astrakhan State Medical University, Ministry of Health of the Russian Federation,

Russia, 414000 Astrakhan, pl. Shaumyana, 1; Russia, 414000 Astrakhan, ul. Bakinskaya, 121

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