title: Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives.
abstract: A series of 4-hydroxybenzene acrylic acid derivatives were designed and synthesized based on the ferulic acid of natural active ingredients. The tested compound 5a, 5f and 6a have significant anti-inflammatory activity with suppression rates of 45.29%, 44.75% and 24.11%, respectively, compared with that of indomethacin, and their cardiac toxicity was not observed. The structure-function relationship shows that the p-hydroxyl group on the α-position benzene ring, particularly if acetylated, contributes to the considerable anti-inflammatory activity; that the carboxyl group on the double bond, if esterified, also contributes to the anti-inflammatory activity; that the p-methylsulfonyl group on the other benzene ring, whose introduction is due to the COX-2 selectivity, also contributes to anti-inflammatory activity surprisingly.
authors.affiliation: School of Pharmaceutical Sciences, Shandong University of Traditional Chinese Medicine, Jinan, China.
authors.forename: Jin-Long
authors.initials: JL
authors.lastname: Mao
authors.forename: Xiang-Kai
authors.initials: XK
authors.lastname: Ran
authors.forename: Jing-Zhen
authors.initials: JZ
authors.lastname: Tian
authors.forename: Bo
authors.initials: B
authors.lastname: Jiao
authors.forename: Hong-Lei
authors.initials: HL
authors.lastname: Zhou
authors.forename: Li
authors.initials: L
authors.lastname: Chen
authors.forename: Zhen-Guo
authors.initials: ZG
authors.lastname: Wang
mesh_terms: D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003373:Coumaric Acids / Q000737:chemistry; D015195:Drug Design; D015394:Molecular Structure; D019800:Phenol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000179:Acrylates; D000893:Anti-Inflammatory Agents; D003373:Coumaric Acids; D019800:Phenol; C004999:ferulic acid; C036658:acrylic acid