Microwave-assisted synthesis of 1,3-benzothiazol-2(3H)-one derivatives and analysis of their antinociceptive activity.

Arzneimittel-Forschung-Drug Research Pub Date : 2012-12-01 Epub Date: 2012-10-19 DOI:10.1055/s-0032-1327613

T Onkol, Y Dündar, E Yıldırım, K Erol, M F Sahin

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引用次数: 3

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.

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微波辅助合成1,3-苯并噻唑-2(3H)- 1衍生物及其抗伤活性分析。

建立了一种在微波辐射条件下快速合成6-酰基-1,3-苯并噻唑-2(3H)- 1衍生物的方法。与传统加热相比，反应时间缩短。此外，用微波辅助法合成了1,3-苯并噻唑-2(3H)- 1、6-酰基-1,3-苯并噻唑-2(3H)- 1、5-酰基-1,3-苯并噻唑-2(3H)- 1和6-酰基-5-氯-1,3-苯并噻唑-2(3H)- 1的乙酸和乙酰胺衍生物，并通过甩尾、夹尾、热板和扭体实验分析了它们的抗炎活性。合成的化合物中，3-[2-(4-乙基哌嗪-1-基)-2-氧乙基]-1,3-苯并噻唑-2(3H)- 1 (6a)、5-氯-3-{2-氧-2-[4-(丙基-2-基)哌嗪-1-基]乙基}-1,3-苯并噻唑-2(3H)- 1 (7e)和3-[2-(4-丁基哌嗪-1-基)-2-氧乙基]-5-氯-1,3-苯并噻唑-2(3H)- 1 (8e)在夹尾、甩尾、热板和扭体实验中表现出显著的抗伤活性。支持信息可在线访问http://www.thieme-connect.de/ejournals/toc/amf。

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来源期刊

Arzneimittel-Forschung-Drug Research 医学-化学综合

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审稿时长

4-8 weeks