S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 1. Synthesis and characterization

Abstract

Purpose: To synthesize and

Novel indole based hybrid oxadiazole scaffolds with N-(substituted-phenyl)butanamides: synthesis, lineweaver–burk plot evaluation and binding analysis of potent urease inhibitors

“…With the help of 1 H-NMR spectrum of this molecule, the indole heterocyclic core was identified clearly by the characteristic signals at δ 10.80 (s, 1H, NH-1), 7.51 (br.d, J = 7.8 Hz, 1H, H-7), 7.34 (br.d, J = 8.1 Hz, 1H, H-4), 7.14 (dist.d, J = 1.8 Hz, 1H, H-2), 7.06 (br.t, J = 7.2 Hz, 1H, H-6) and 6.97 (br.t, J = 7.2 Hz, 1H, H-5) ppm. 12 Similarly, the resonances at δ 7.21 (br.d, J = 7.9 Hz, 1H, H-6′′′′), 7.00 (br.s, 1H, H-3′′′′), 6.94 (br.d, J = 7.7 Hz, 1H, H-5′′′′), along with two methyl signals at δ 2.23 (s, 3H, CH 3 -4′′′′) and 2.12 (s, 3H, CH 3 -2′′′′) ppm, were typical for a 2,4-dimethylphenyl group in the molecule. The C and N -substituted butanamide group was identified by four signals at δ 9.25 (s, 1H, CONH-1), 3.27 (t, J = 7.1 Hz, 2H, CH 2 -4′′′), 2.47 (t, J = 7.2 Hz, 2H, CH 2 -2′′′) and 2.06–2.01 (m, 4H, CH 2 -3′′′ & CH 2 -2′).…”

“…10,11 The bioactivity of indole and oxadiazole moieties prompted us to synthesize some new butanamide molecules bearing these moieties altogether. Hence, in continuation of our previous efforts on bioactivity study of indole containing compounds 12,13 and urease inhibitory activity of bi-heterocyclic bi-amide molecules, 14 the present investigation was designed to explore the urease inhibitory potential and the kinetic mechanism of newly synthesized bi-heterocyclic butanamides. The binding interactions with the targeted enzyme were ascertained by molecular docking, and the cytotoxicity of these scaffolds was evaluated by hemolysis to identify their therapeutic utility as promising drug candidates in drug discovery programs.…”

Synthesis and Fungicidal Activities of 5-Aryl-1,3,4-oxadiazolyl 2-Thioether Derivatives Containing Strobilurin Motif

“…1,3,4-Oxadiazole compounds have been known for about 90 years, 15 and the investigation of their biological activities has intensified in the last thirty years. Notably, these compounds exhibit a wide range of pharmacological activities, having anticancer 16,17 antibacterial, [18][19][20] fungicidal, 21,22 herbicidal, 23,24 and insecticidal [25][26][27] effects. In particular, the presence of an -N=C-O moiety in 1,3,4-oxadiazole compounds enhances the biological activity because this moiety can form hydrogen bonds with electron-rich target sites.…”