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

T. Önkol; Y. Dündar; E. Yıldırım; K. Erol; M. F Şahin

doi:10.1055/s-0032-1327613

Arzneimittelforschung, Table of Contents

Arzneimittelforschung 2012; 62(12): 571-575
DOI: 10.1055/s-0032-1327613

Original Article

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

T. Önkol

¹Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey

,

Y. Dündar

¹Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey

,

E. Yıldırım

²Department of Pharmacology, Faculty of Medicine, Osmangazi University, Eskişehir, Turkey

,

K. Erol

²Department of Pharmacology, Faculty of Medicine, Osmangazi University, Eskişehir, Turkey

,

M. F Şahin

¹Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, Turkey

› Author Affiliations

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

Full Text

References

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