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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Synthesis, Antimicrobial Activity, and Molecular Docking of N-Phenylcarbamate Derivatives with a Heterocyclic Moiety

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PII
S30346304S0514749225050083-1
DOI
10.7868/S3034630425050083
Publication type
Article
Status
Published
Authors
A. V. Velikorodov
  • Affiliation:
    Tatishchev Astrakhan State University
    Astrakhan State Medical University, Ministry of Health of the Russian Federation
S. V. Borisova
  • Affiliation: Razumovsky Saratov State Medical University, Ministry of Health of the Russian Federation
E. A. Shustova
  • Affiliation: Astrakhan State Medical University, Ministry of Health of the Russian Federation
E. N. Kutlalieva
  • Affiliation:
    Tatishchev Astrakhan State University
    Astrakhan State Medical University, Ministry of Health of the Russian Federation
Volume/ Edition
Volume 61 / Issue number 5
Pages
572-584
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.
Keywords
карбаматные производные бензимидазола пиридазина N-аллильные производные 2-морфолиноэтил-N-фенилкарбамата и 2-(2-пиридинил)этил-N-фенилкарбамата молекулярный докинг глюкозамин-6-фосфатсинтаза противомикробная активность
Date of publication
12.12.2025
Year of publication
2025
Number of purchasers
0
Views
48

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