Synthesis, characterization, antituberculosis activity and computational studies on novel Schiff bases of 1,3,4-thiadiazole derivatives

Abstract

A series of novel Schiff bases were designed and synthesized by the condensation of 1,3,4-thiadiazoles that contain aromatic primary amine and variously substituted benzaldehydes. The synthesized compounds were screened for their antituberculosis activity against Mycobacterium tuberculosis H37Rv using BACTEC 460 radiometric system. Among the tested compounds, 2-(4-nitrophenyl)amino-5-[4-(3-(4-phenoxy))benzylideneaminophenyl]-1,3,4thiadiazole (3n) showed the highest inhibitory activity (80%). The activities of the newly synthesized Schiff bases were higher in comparison to those of intermediate products 2-(4-aminophenyl)-5-aryl/alkylamino-1,3,4thiadiazoles (2a-l). The computational studies were also performed to estimate drug-like profile of the compounds by using QikProp analysis.

A Comprehensive Examination of Heterocyclic Scaffold Chemistry for Antitubercular Activity

“…When the target compounds were evaluated for their anti-tubercular activities, the results proved to be interesting with (496n) showing inhibition upto 80 %. (Scheme 95) [110] Panchani et al developed a greener route for the synthesis of various substituted pyrazole derivatives by using condensation reaction between imidazole and different acetophenones to form chalcones which was further reacted with phenyl hydrazine in presence of green solvent polyethylene glycol-400 (PEG-400). The synthesized pyrazole derivatives were screened for their anti-tubercular activity and it was shown that the compound 501a was most active with inhibition of 98.17 and 94.37 % at the concentration of 12.5 μg/mL in dormant and active stages respectively.…”

“…When the target compounds were evaluated for their anti‐tubercular activities, the results proved to be interesting with (496n) showing inhibition upto 80 %. (Scheme 95) [110] …”