Novel Benzo[b]thienylhydrazine and 1,3,4‐Oxadiazole Derivatives as Potential Antidepressant Agents

Abstract

Three novel series of benzo[b]thiophene derivatives bearing various hydrazone, hydrazine and 1,3,4-oxadiazole moieties were synthesized as potential antidepressant agents. 22 Compounds were evaluated for their in vitro inhibitory effect on monoamine oxidase enzyme (MAO) type A. Several compounds inhibited MAO stronger than pargyline hydrochloride. Maximum inhibitions of 83% and 90% were observed with 1-benzyl-2-(3-chlorobenzo[b]thienyl-2-carbonyl)hydrazine (24) and 1-[2-(4-chlorophenyl)ethyl]-2-(3-chlorobenzo[b]thienyl-2- carbonyl)hydrazine (35), respectively.

New non-symmetrical 2,5-disubstituted-1,3,4-oxadiazoles bearing a benzo[b]thiophene moiety

“…In the 13 C-NMR spectra of compounds 4a-g, the two carbon atoms from the oxadiazole ring appear at ca. 160 ppm for the one linked to the benzo[b]thiophene moiety and at ca.…”

“…The elemental analysis was performed on a COSTECH Instruments EAS32 apparatus. The NMR spectra were recorded on a Varian Gemini 300 BB instrument, operating at 300 MHz for 1 H and 75 MHz for 13 C, in DMSO-d 6 or CDCl 3 , using TMS as internal standard. Mass spectra were obtained on a Finnigan MAT 90 spectrometer using CI technique (150eV, isobutane).…”

“…Several 1,3,4-oxadiazoles bearing the 3-chlorobenzo [b]thienyl moiety are known and were screened for antimicrobial activity. 12,13 The 2-amino-5-(3-chloro-benzothienyl) derivatives were synthesized by cyclodesulfurization of thiosemicarbazides, 12 while the corresponding 2-thioether-derivatives were obtained by alkylation of an 1,3,4-oxadiazole-2-thione. 13 To our knowledge a study concerning the synthesis of unsymmetrical 2,5-diaryl-1,3,4-oxadiazoles substituted with a benzo[b]thiophene ring has not been reported.…”

“…12,13 The 2-amino-5-(3-chloro-benzothienyl) derivatives were synthesized by cyclodesulfurization of thiosemicarbazides, 12 while the corresponding 2-thioether-derivatives were obtained by alkylation of an 1,3,4-oxadiazole-2-thione. 13 To our knowledge a study concerning the synthesis of unsymmetrical 2,5-diaryl-1,3,4-oxadiazoles substituted with a benzo[b]thiophene ring has not been reported. Herein, we describe the synthesis and characterization of 2,5-disubstituted-1,3,4-oxadiazoles bearing a benzo [b]thiophene ring by dehydration of unsymmetrical N,N'-diacylhydrazines.…”

Design and synthesis of oxaprozin‐1,3,4‐oxadiazole hybrids as potential anticancer and antibacterial agents

“…Development of several techniques for the facile construction of the scaffold had captured acceleration . Over the last decade, approximately 686 patents have been filed on oxadiazole pharmacophore and its importance 2,5‐Disubstituted oxadiazole subsidiaries have been encompassed with promising pharmacological profiles such as anticancer, antitubercular, antimicrobial, antifungal, antiepileptic, analgesic, antitumour, ulcerogenic, hypoglycaemic, central nervous system, antidepressant, hypnotic and sedative properties . Few compounds viz., zibotentan, ataluren, and raltegravir (Figure ) comprising oxadiazole as core nucleus are in the late stages of clinical trials substantiating the valuable privileges of the scaffold.…”