Tehran University of Medical Sciences

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Novel 5-(Nitrothiophene-2-Yl)-1,3,4-Thiadiazole Derivatives: Synthesis and Antileishmanial Activity Against Promastigote Stage of Leishmania Major Publisher



Sadatebrahimi SE1 ; Mirmohammadi M1 ; Tabatabaei ZM2 ; Arani MA3 ; Jafariashtiani S1 ; Hashemian M1 ; Foroumadi P1 ; Yahyameymandi A1 ; Moghimi S3 ; Moshafi MH4 ; Norouzi P1 ; Ardestani SK2 ; Foroumadi A1, 3
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Source: Iranian Journal of Pharmaceutical Research Published:2019


Abstract

In this study, a series of novel compounds based on 5-(5-nitrothiophene2--yl)-1,3,4-thiadiazole possessing (het) aryl thio pendant at C-2 position of thiadiazole ring is developed and evaluated as antileishmanial agents using MTT colorimetric assay. 10 New compounds containing aryl and heteroaryl derivatives, started from thiophene-2-carbaldehyde in five steps, were synthesized in good to excellent yields and characterized by1H-NMR,13C-NMR, and IR spectroscopy. Through the compounds 6a-j, methylimidazole containing derivative 6e was recognized as the most active compound against L. major promastigotes exhibiting IC50 values of 11.2µg/mL and 7.1µg/mL after 24 and 48 h, respectively. This compound is > 4 fold more effective than Glucantime as a standard drug (IC50 = 50 µg/mL after 24 h and 25 µg/mL after 48 h). © 2019, Iranian Journal of Pharmaceutical Research. All rights reserved.