Properties and synthesis of 2-{2-fluoro (or bromo)-4-[(2-oxocyclopentyl) methyl]phenyl}propanoic acid

Nonsteroidal anti-inflammatory drugs with low membrane permeabilizing and gastric lesion-producing activities

Naoki Yamakawa, Shintaro Suemasu, Masaaki Matoyama, Ayumi Kimoto, Miho Takeda, Ken Ichiro Tanaka, Tomoaki Ishihara, Takashi Katsu, Yoshinari Okamoto, Masami Otsuka, Tohru Mizushima

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

We previously proposed that membrane permeabilization activity of NSAIDs is involved in NSAID-induced gastric lesions. We here synthesized derivatives of loxoprofen that have lower membrane permeabilization activity than other NSAIDs. Compared to loxoprofen, the derivatives 10a and 10b have lower membrane permeabilization activity and their oral administration produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 10a and 10b are likely to be therapeutically beneficial as safer NSAIDs.

Original languageEnglish
Pages (from-to)7879-7882
Number of pages4
JournalJournal of Medicinal Chemistry
Volume53
Issue number21
DOIs
Publication statusPublished - 2010 Nov 11
Externally publishedYes

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Non-Steroidal Anti-Inflammatory Agents
Stomach
Anti-Inflammatory Agents
Membranes
Pharmaceutical Preparations
Oral Administration
propionic acid
loxoprofen

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

Properties and synthesis of 2-{2-fluoro (or bromo)-4-[(2-oxocyclopentyl) methyl]phenyl}propanoic acid : Nonsteroidal anti-inflammatory drugs with low membrane permeabilizing and gastric lesion-producing activities. / Yamakawa, Naoki; Suemasu, Shintaro; Matoyama, Masaaki; Kimoto, Ayumi; Takeda, Miho; Tanaka, Ken Ichiro; Ishihara, Tomoaki; Katsu, Takashi; Okamoto, Yoshinari; Otsuka, Masami; Mizushima, Tohru.

In: Journal of Medicinal Chemistry, Vol. 53, No. 21, 11.11.2010, p. 7879-7882.

Research output: Contribution to journalArticle

Yamakawa, Naoki ; Suemasu, Shintaro ; Matoyama, Masaaki ; Kimoto, Ayumi ; Takeda, Miho ; Tanaka, Ken Ichiro ; Ishihara, Tomoaki ; Katsu, Takashi ; Okamoto, Yoshinari ; Otsuka, Masami ; Mizushima, Tohru. / Properties and synthesis of 2-{2-fluoro (or bromo)-4-[(2-oxocyclopentyl) methyl]phenyl}propanoic acid : Nonsteroidal anti-inflammatory drugs with low membrane permeabilizing and gastric lesion-producing activities. In: Journal of Medicinal Chemistry. 2010 ; Vol. 53, No. 21. pp. 7879-7882.
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AU - Ishihara, Tomoaki

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