Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Abstract

Seventeen new furan‐substituted thiadiazolyl hydrazone derivatives bearing 4‐nitrophenyl moiety were designed, synthesized and tested for their in vitro antimicrobial activity. Reaction of N‐(4‐nitrophenyl)‐C‐(furan‐2‐yl)methanohydrazonoyl chloride 1 with 2‐((methylthio)carbonthioyl)hydrazine derivatives 3, 7, 8 and 11–13 in absolute ethanol in the presence of triethylamine at room temperature afforded the corresponding 1,3,4‐thiadiazole derivatives 6, 9, 10 and 14–16. Refluxing of 1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1H‐pyrazol‐4‐yl)ethan‐1‐one 17 with methyl hydrazinecarbodithioate 18 in absolute ethanol in the presence of few drops of hydrochloric acid yielded methyl‐2‐(1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1H‐pyrazol‐4‐yl)ethylidene)hydrazine‐1‐carbodithioate 19. The compound 19 was reacted with hydrazonoyl halides 20a‐e in absolute ethanol in the presence of triethylamine afforded the corresponding 1,3,4‐thiadiazoles 24a‐e. The specified compounds were tested for antimicrobial activity against selected model microorganisms. Antimicrobial studies revealed that compounds 6c, 6d and 15 against E. coli, compounds 6b, 6c, 10, 14, 15, 24b and 24c against B. mycoides, and compounds 14, 16, 19 and 24d against C. albicans outperformed other developed compounds in terms of antimicrobial activity.

Cytotoxic Effect of New (E)‐2‐Cyano‐N‐(tetrahydrobenzo[b]thiophen‐2‐yl)acrylamide Derivatives: Down‐Regulation of RBL2 and STAT2 and Triggering of DNA Damage in Breast Carcinoma

“…[17] Moreover, thiophenes have useful applications as kinase inhibitors 24] and as anti-Alzheimer drugs. [25] Based on these facts and in continuation to our research interest in the synthesis of bioactive compounds [3,4,18,[26][27][28][29][30][31][32][33][34][35] we report herein the synthesis of novel series of cyanoacrylamides linked to tetrahydrobenzo[b]thiophene moiety and test their cytotoxic activities against various cancer cell lines using MTT assay.…”

Synthesis and Anti‐Bacterial Evaluation of Novel Scaffolds Based on Bis‐Thiazole or bis‐1,3,4‐Thiadiazole Linked to Thieno[2,3‐b]Thiophene as New Hybrid Molecules

“…Subsequent elimination of methyl mercaptan from II afforded the final products 13 a-n (Scheme 4). [75][76][77] The scope of the reaction was broadened by examining the use of 4-bis(2-carbamothioyl)hydrazine 7 rather than bis-2-(methylthiocarbonothioyl)hydrazine 6 as a precursor. The reaction of 7 with hydrazonoyl chlorides 9 a-f opens the door to novel bis [5-(2-arylhydrazono) Compounds 15 a-f were identified using elemental analyses and spectral data to confirm their proposed structures.…”

Design, synthesis, structure elucidation, antimicrobial, molecular docking, and SAR studies of novel urea derivatives bearing tricyclic aromatic hydrocarbon rings

“…It is more difficult to eliminate or eradicate them completely; so, discovering and looking for new moieties is highly desirable to tackle a progress emergence of multidrug resistance in the present times. [72][73][74][75][76] F I G U R E 1 Some approved drugs bear urea, fluorene, and phenothiazine derivatives along with the designed tricyclic ring containing urea derivatives.…”