title: Microwave-assisted synthesis of 1,3-benzothiazol-2(3H)-one derivatives and analysis of their antinociceptive activity.
abstract: A rapid and efficient method was developed for synthesis of 6-acyl-1,3-benzothiazol-2(3H)-one derivatives under microwave irradiation (MWI) conditions. The reaction times were shortened compared to conventional heating. Additionally, we synthesized acetic acid and acetamide derivatives of 1,3-benzothiazol-2(3H)-one, 6-acyl-1,3-benzothiazol-2(3H)-one, 5-chloro-1,3-benzothiazol-2(3H)-one and 6-acyl-5-chloro-1,3-benzothiazol-2(3H)-one with the microwave-assisted method and analyzed their antinociceptive activity with the tail flick, tail clip, hot plate and writhing tests. Among the synthesized compounds, 3-[2-(4-ethylpiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2(3H)-one (6a), 5-chloro-3-{2-oxo-2-[4-(propan-2-yl) piperazin-1-yl]ethyl}-1,3-benzothiazol-2(3H)-one (7e) and 3-[2-(4-butylpiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2(3H)-one (8e) showed significant antinociceptive activity in the tail clip, tail flick, hot plate and writhing tests. Supporting Information available online at http://www.thieme-connect.de/ejournals/toc/amf.
authors.affiliation: Department of Pharmaceutical Chemistry, Gazi University, Ankara, Turkey.
authors.forename: T
authors.initials: T
authors.lastname: Onkol
authors.forename: Y
authors.initials: Y
authors.lastname: Dündar
authors.forename: E
authors.initials: E
authors.lastname: Yıldırım
authors.forename: K
authors.initials: K
authors.lastname: Erol
authors.forename: M F
authors.initials: MF
authors.lastname: Sahin
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D000818:Animals; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D006358:Hot Temperature; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008872:Microwaves; D010147:Pain Measurement / Q000379:methods; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000700:Analgesics; D052160:Benzothiazoles; D007202:Indicators and Reagents