Preparation and biological activity of 2-[4-(thiazol-2-yl)phenyl]propionic acid derivatives inhibiting cyclooxygenase.

doi:10.1248/CPB.39.2323

Paper

Preparation and biological activity of 2-[4-(thiazol-2-yl)phenyl]propionic acid derivatives inhibiting cyclooxygenase.

Published Sep 25, 1991 · Y. Naito, T. Goto, F. Akahoshi

Chemical & pharmaceutical bulletin

Q3 SJR score

6

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A series of 2-[4-(thiazol-2-yl)phenyl]propionic acids substituted at various positions were prepared by the reaction of diethyl 2-methyl-2-(4-thiocarbamoylphenyl)malonates with alpha-bromoaldehyde diethyl acetals or alpha-haloketones followed by hydrolysis of esters. The inhibition of prostaglandin H synthetase (cyclooxygenase) was assayed by use of an enzyme preparation from guinea pig polymorphonuclear leukocytes. Examination of the structure-activity relationship of these compounds indicated that the substitution pattern with halogens at position 3 (R1) of the benzene ring and a methyl group in position 4 (R2) and/or 5 (R3) of the thiazole ring were favorable for inhibitory activity. The compounds bearing bulky alkyl or polar functional groups at the R2 position were weak inhibitors. The potent inhibitors of cyclooxygenase were tested for their ability to reduce carrageenin-induced inflammation of rat paws. These derivatives had strong anti-inflammatory activity based on their strong inhibition of cyclooxygenase, with some exceptions, including those with a thiomethyl group at R1.

In Vitro Study

Study Snapshot

2-[4-(thiazol-2-yl)phenyl]propionic acid derivatives with halogens at position 3 and methyl groups at positions 4 and 5 show strong anti-inflammatory activity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Preparation and biological activity of 2-[4-(thiazol-2-yl)phenyl]propionic acid derivatives inhibiting cyclooxygenase.

Sign up to use Study Snapshot

References

Citations

Microwave Promoted Alkylation of Halonitrobenzene with Malonates in Solvent-free Medium

Microwave-promoted alkylation of halonitrobenzene with malonates in solvent-free medium offers mild reaction conditions, high regio-selectivity, rapid conversions, and easy product isolation.

The sonochemical arylation of active methylene compounds.

Sonochemical arylation of active methylene compounds with haloarenes yields slightly better results than classical experiments, with the exception of reactions with phenylsulfonylacetonitrile.

1,4‐Dichloro‐2‐butanone

1,4-dichloro-2-butanone is a highly toxic and irritating chemical, potentially causing respiratory problems and causing military poisoning.

Quantitative structure-activity relationships of 2-[4-thiazol-2-yl)phenyl]-propionic acid derivatives inhibiting cyclooxygenase

2-[4-(thiazol-2-yl)phenyl]propionic acid derivatives inhibit cyclooxygenase more effectively with short-length, high electron-donating, and hydrophobic substituents on the thiazole ring.

QSAR Studies on Thiazolidines: A Biologically Privileged Scaffold

Thiazolidines show diverse biological activities, with their structural features and physicochemical properties influencing their activity behavior.