Synthesis, Structural Characterization and Enzyme Inhibition Studies on 5-(2-Nitrostyryl)-1,3,4-Oxadiazole-2-Thiol Derivatives

Abstract

In the present work, S-substituted derivatives of 5-(2-nitrostyryl)-1,3,4-oxadiazole-2-thiol (4) were synthesized by successive conversions of 3-(2-nitrophenyl) acrylic acid (1) into its respective ester, hydrazide and 1,3,4-oxadiazole. Finally the target compounds were obtained by reaction of 5-(2-nitrostyryl)-1,3,4-oxadiazole-2-thiol (4) with a series of various electrophiles, (5a-I), in N,N-dimethyl formamide (DMF) in the presence of sodium hydride (NaH). The structural characterization of these newly synthesized compounds was done by IR, 1 H-NMR, HR-MS and EI-MS spectral data. All these compounds were evaluated for their enzyme inhibitory potentials and found to exhibit broad range spectrum against acetylcholinesterase, butyrylcholinestrase and lipoxygenase enzymes.

S-Alkylated/aralkylated 2-(1H-indol-3-yl-methyl)-1,3,4- oxadiazole-5-thiol derivatives. 2. Anti-bacterial, enzymeinhibitory and hemolytic activities

“…Compound 6p has S-substituted 4-chlorobenzyl group which might have been responsible for its better fitting into the active site of BChE [22]. Compounds 3-({5-[(2-chlorobenzyl)sulfanyl]-1,3,4-oxadiazol-2-yl}methyl)-1H-indole (6n) and 3-({5-[(4-chlorobenzyl)sulfanyl]-1,3,4-oxadiazol-2-yl}methyl)-1H-indole (6p) which possess 2-chlorobenzyl and 4-chlorobenzyl substituents respectively, showed good inhibitory potential against LOX, relative to standard Baicalein [23].…”

“…In continuation of our ongoing research efforts in search for new anti-bacterial, hemolytic and antienzymatic agents [9,10], we report herein the pharmacological activities of Salkylated/aralkylated 2-[1H-indol-3-ylmethyl]-1,3,4-oxadiazole-5-thiols (6a-u)…”

Synthesis of 2-{[5-(aralkyl/aryl)-1,3,4-oxadiazol-2- yl]sulfanyl}-N-(4-methyl-1,3-thiazol-2-yl)acetamides: Novel bi-heterocycles as potential therapeutic agents

“…In addition, high antioxidant, anti-inflammatory and inhibitory effects of thiazoles have been observed in vitro in their action against parasites (Plasmodium and Trypanosoma) and fungi (Candida albicans) [2]. Similarly, 1,3,4-oxadiazoles have demonstrated a range of bioactivities [3][4][5].Molecules bearing this moiety are known to possess anti-parasitic, hypoglycemic, anti-inflammatory, antifungal and antibacterial activities [6][7][8].…”

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

“…The appropriate aromatic acids are transformed to corresponding oxadiazoles through their hydrazides [7,8]. Substitution of alkyl/aralkyl halides can be done at 1, 3, 4-oxadiazole-2-thiol, to study structure-activity relationship [9].…”

“…It is obtained naturally from diets rich in vegetable stems and is synthesized from tryptophan, which is also used for the hormones serotonin and melatonin, the anti-inflammatory drug indomethacin, the psychotropic drug LSD and the anti-tumor agent vinblastine [10,11]. In continuation of our ongoing research efforts [12,13], we report herein the synthesis of alkylated/aralkylated 2-[1H-indol-3-ylmethyl]-1,3,4-oxadiazole-5-thiols (6a-u) which might be employed for pharmacological evaluation in search of new drug candidates.…”