Синтез, антиексудативна та антимікробна активність 6-арилідензаміщених імідазо[2,1-b]тіазолів

Lesya M. Saliyeva; Serhii M. Holota; Alina M. Grozav; Nina D. Yakovychuk; Mykola M. Lukashchuk; Larysa P. Marushko; Nataliia Yu. Slyvka; Mykhailo V. Vovk

doi:10.24959/ophcj.21.227378

Authors

Lesya M. Saliyeva Lesya Ukrainka Volyn National University, Ukraine https://orcid.org/0000-0002-1047-8652
Serhii M. Holota Lesya Ukrainka Volyn National University; Danylo Halytsky Lviv National Medical University, Ukraine https://orcid.org/0000-0002-9892-437X
Alina M. Grozav Bukovinian State Medical University, Ukraine https://orcid.org/0000-0001-9821-0695
Nina D. Yakovychuk Bukovinian State Medical University, Ukraine https://orcid.org/0000-0003-1332-9510
Mykola M. Lukashchuk Rivne Medical Academy; Lesya Ukrainka Volyn National University, Ukraine https://orcid.org/0000-0001-9177-7808
Larysa P. Marushko Lesya Ukrainka Volyn National University, Ukraine https://orcid.org/0000-0002-8373-6747
Nataliia Yu. Slyvka Lesya Ukrainka Volyn National University, Ukraine https://orcid.org/0000-0002-3811-7138
Mykhailo V. Vovk Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine https://orcid.org/0000-0001-7739-670X

DOI:

https://doi.org/10.24959/ophcj.21.227378

Keywords:

2-methyl-2,3-dihydroimidazo[2,1-b]thiazolone; arylaldehydes; Knoevenagel condensation; 6-arylidene-2-methyl-2,3-dihydroimidazo[2,1-b]thiazolones; antiexudative activity; antimicrobial activity

Abstract

Aim. To expand the range of 6-arylidene-2-methyl-2,3-dihydroimidazo[2,1-b]thiazolones as potential objects for studying the antiexudative and antimicrobial activities.

Results and discussion. It has been shown that the condensation of synthetically affordable 2-methyl-2,3-dihydroimidazo[2,1-b]thiazolone with aromatic aldehydes can be successfully used for obtaining the corresponding 6-ylidene-functionalized derivatives. The biological screening of the compounds synthesized revealed that they possessed a low or moderate anti-inflammatory activity and inhibited the inflammation process in the range from 3 to 44 %. During the study of the antimicrobial activity of the substances obtained it was determined that their minimum bacteriostatic and minimum fungistatic concentrations ranged from 31.25 to 250 μg/mL.

Experimental part. The interaction of 2-methyl-2,3-dihydroimidazo[2,1-b]thiazolone with a series of benzaldehydes and salicylic aldehydes in refluxing acetic acid in the presence of anhydrous sodium acetate leads to new 6-arylidene-2-methyl-2,3-dihydroimidazo[2,1-b]thiazolones. The antiexudative activity screening was performed on the model of carrageenan-induced paw oedema of white outbred male rats. The antimicrobial activity of the compounds was studied using the microtechnique of two-fold serial dilutions in a liquid nutrient medium.

Conclusions. It has been found that the Knoevenagel condensation of 2-methyl-2,3-dihydroimidazo[2,1-b]thiazolone with aromatic aldehydes is a convenient way for the structural modification of the position 6 of the heterocyclic system by the arylidene moiety. The arylidene derivatives obtained show a moderate antiexudative activity in the carrageenan-induced rat paw oedema assay, as well as the antimicrobial activity against some gram-positive and gram-negative bacteria and fungi.

Supporting Agency

Роботу виконано відповідно до основного напряму досліджень кафедри органічної хімії та фармації Волинського національного університету ім. Лесі Українки «Синтез та функціоналізація конденсованих сполук, які є похідними імідазолів, тіазолів, піридинів, та дослідження їх біологічної активності» (протокол №2 від 16.09.2020), у рамках бюджетних наукових тем відділу механізмів органічних реакцій ІОХ НАН України «Дослідження закономірностей циклоутворення та структурна модифікація нових типів функціональних азинових і азепінових систем» (№ держреєстрації: 0115U004724, період досліджень: 2016 – 2020 рр.), кафедри медичної та фармацевтичної хімії та кафедри мікробіології та вірусології Буковинського державного медичного університету «Цілеспрямоване конструювання потенційно біоактивних систем на основі нітрогеновмісних гетероциклів» (№ держреєстрації: 0120U101532, період досліджень: 2020 – 2024 рр.).

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