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Arzneimittelforschung 2012; 62(12): 571-575
DOI: 10.1055/s-0032-1327613
Original Article
© Georg Thieme Verlag KG Stuttgart · New York

Microwave-Assisted Synthesis of 1,3-Benzothiazol-2(3H)-one Derivatives and Analysis of Their Antinociceptive Activity

T. Önkol
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey
,
Y. Dündar
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey
,
E. Yıldırım
2   Department of Pharmacology, Faculty of Medicine, Osmangazi University, Eskişehir, Turkey
,
K. Erol
2   Department of Pharmacology, Faculty of Medicine, Osmangazi University, Eskişehir, Turkey
,
M. F Şahin
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey
› Author Affiliations
Further Information

Publication History

received 29 June 2012

accepted 14 September 2012

Publication Date:
19 October 2012 (online)

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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

Key words

1,3-benzothiazol-2(3H)-one - tail flick test - tail clip test - hot plate test - writhing test - microwave-assisted synthesis

Supporting Information

 

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