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

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-benzot...

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Published inArzneimittel-Forschung Vol. 62; no. 12; pp. 571 - 575
Main Authors Onkol, T., Dundar, Y., Yildirim, E., Erol, K., Sahin, M. F.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.2012
Subjects
Analgesics - chemical synthesis
Analgesics - pharmacology
Analgesics - toxicity
Animals
Benzothiazoles - chemical synthesis
Benzothiazoles - pharmacology
Benzothiazoles - toxicity
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Hot Temperature
Humans
Indicators and Reagents
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Mice
Microwaves
Pain Measurement - methods
Pharmacology & Pharmacy
Physical Sciences
Reaction Time - drug effects
Science & Technology
Structure-Activity Relationship
microwave-assisted synthesis
writhing test
1,3-benzothiazol-2(3H)-one
hot plate test
tail clip test
tail flick test
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Summary: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.
ISSN:0004-4172
1616-7066
DOI:10.1055/s-0032-1327613