title: Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid: nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity.
abstract: We previously reported that 2-fluoroloxoprofen has lower gastric ulcerogenic activity than loxoprofen, a nonsteroidal anti-inflammatory drug (NSAID) without selectivity for COX-2. We synthesized derivatives of 2-fluoroloxoprofen and studied their properties. Compared to 2-fluoroloxoprofen, one derivative, 11a, exhibited higher anti-inflammatory activity and an equivalent ulcerogenic effect. These results suggest that 11a could be therapeutically beneficial for use as an NSAID.
authors.affiliation: Department of Analytical Chemistry, Faculty of Pharmacy, Keio University, Tokyo 105-8512, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Yamakawa
authors.forename: Shintaro
authors.initials: S
authors.lastname: Suemasu
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Okamoto
authors.forename: Ken-Ichiro
authors.initials: K
authors.lastname: Tanaka
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Ishihara
authors.forename: Teita
authors.initials: T
authors.lastname: Asano
authors.forename: Keishi
authors.initials: K
authors.lastname: Miyata
authors.forename: Masami
authors.initials: M
authors.lastname: Otsuka
authors.forename: Tohru
authors.initials: T
authors.lastname: Mizushima
mesh_terms: D000814:Aniline Compounds / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology; D002351:Carrageenan; D051545:Cyclooxygenase 1 / Q000378:metabolism; D051546:Cyclooxygenase 2 / Q000378:metabolism; D016861:Cyclooxygenase Inhibitors / Q000009:adverse effects / Q000138:chemical synthesis / Q000494:pharmacology; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D006801:Humans; D010666:Phenylpropionates / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013276:Stomach Ulcer / Q000139:chemically induced*; D013329:Structure-Activity Relationship
chemical_list: C575278:2-(4-(cyclopentylamino)-2-fluorophenyl)propanoic acid; D000814:Aniline Compounds; D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D010666:Phenylpropionates; D002351:Carrageenan; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2