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

doi:10.1021/jm101116s

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 journal › Article › peer-review

18 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 language	English
Pages (from-to)	7879-7882
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	53
Issue number	21
DOIs	https://doi.org/10.1021/jm101116s
Publication status	Published - 2010 Nov 11

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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Yamakawa, N., Suemasu, S., Matoyama, M., Kimoto, A., Takeda, M., Tanaka, K. I., Ishihara, T., Katsu, T., Okamoto, Y., Otsuka, M., & Mizushima, T. (2010). 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. Journal of Medicinal Chemistry, 53(21), 7879-7882. https://doi.org/10.1021/jm101116s

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 et al.

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

Research output: Contribution to journal › Article › peer-review

Yamakawa, N, Suemasu, S, Matoyama, M, Kimoto, A, Takeda, M, Tanaka, KI, Ishihara, T, Katsu, T, Okamoto, Y, Otsuka, M & Mizushima, T 2010, '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', Journal of Medicinal Chemistry, vol. 53, no. 21, pp. 7879-7882. https://doi.org/10.1021/jm101116s

Yamakawa N, Suemasu S, Matoyama M, Kimoto A, Takeda M, Tanaka KI et al. 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. Journal of Medicinal Chemistry. 2010 Nov 11;53(21):7879-7882. doi: 10.1021/jm101116s

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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.",

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AU - Ishihara, Tomoaki

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AU - Otsuka, Masami

AU - Mizushima, Tohru

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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

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