Synthesis and antibacterial activity of some novel 2-Aroylimino-3-aryl-thiazolidin-4-ones

Abstract

Este trabalho relata uma síntese eficiente e regio-seletiva de algumas 2-aroylimino-3-arylthiazolidin-4-ones (2a-j) envolvendo a ciclização de 1-aroyl-3-aryl tio-uréias em meio básico com cloreto de cloroacetila em dioxana. As estruturas foram confirmadas por dados espectroscópicos, análises elementares e, em um caso (2j), por dados de difração de raios X tipo cristal único. Os compostos foram testados in vitro quanto à sua atividade antimicrobiana em relação a bactérias Gram positivas e Gram negativas. Os resultados revelaram uma atividade promissora desses compostos em relação aos microorganismos testados, comparando-se e, em alguns casos, até superando a atividade das drogas existentes.An efficient, regioselective synthesis of some 2-aroylimino-3-aryl-thiazolidin-4-ones (2a-j) involving base-catalyzed cyclization of 1-aroyl-3-aryl thioureas with chloroacetyl chloride in dioxane is reported. The structures were confirmed by spectroscopic data, elemental analyses and in one case (2j) by single crystal X-ray diffraction data. Compounds (2a-j) were assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria and were found to exhibit promising activity towards the tested microorganisms, comparable to and in some cases better than those of the standard drugs.

Synthesis and antimicrobial activities of a new class of 6-arylbenzimidazo[1,2-c]quinazolines

“…33,34 The absence of aminophenyl ring absorption at 3350 cm -1 and appearance of a strong intensity band in the IR spectra of compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) in the range of 1610-1650 cm -1 attributable to nC=N provides a strong evidence for the condensation and also confirms the formation of the azomethines 1-10. 35 The oxidative cyclisation of compounds 1-10 to 11-20 were accompanied by the disappearance of the absorption maxima at 3150-3300 cm -1 , which are ascribed to the vibrations of NH group of the benzimidazole ring; at the same time the appearance of a new maximum at 1360-1388 cm --1 , which is characteristic for benzimidazoquinazoline ring with a tertiary nitrogen atom, appears.…”

“…Nitrogen heterocycles in particular exhibit diverse biological and pharmacological activities [4][5][6] due in part to the similarities with many natural and synthetic molecules with known biological activity. 7 Moreover, benzimidazoles and quinazolines are of the most extensively studied classes of heterocyclic compounds, and have received much attention from synthetic organic as well as medicinal chemists, because of the diverse range of their biological activities 8,9 and their applications in several areas as materials in electronics, in electrochemistry as anticorrosive agents, as polymers or optical materials and fluorescent tags in DNA sequencing.…”

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“…Compound 13 (towards B. subtilis: 34mm and P. aueroginosa: 33mm was found to exhibit promising activity and was better than standard drug, tetracycline 13 . Results demonstrated that the compounds significantly reduced ascites tumor volume, cell number, and increased the life span of EAT-bearing mice.…”

In silico Screening of Thiazolidine 4-one Derivatives for Antitumor Activity

“…Antifungal, 9 Antioxidant, 11 Cytotoxic, 12 Antiinflammatory, Analgesic, 13 Anti YFV (yellow fever virus) activity, 14 Antitubercular, 15 Antimicrobial,…”