Salicylate-urea-based soluble epoxide hydrolase inhibitors with high metabolic and chemical stabilities

Takeo Kasagami; In Hae Kim; Hsing Ju Tsai; Kosuke Nishi; Bruce D. Hammock; Christophe Morisseau

doi:10.1016/j.bmcl.2009.01.069

Salicylate-urea-based soluble epoxide hydrolase inhibitors with high metabolic and chemical stabilities

Takeo Kasagami, In Hae Kim, Hsing Ju Tsai, Kosuke Nishi, Bruce D. Hammock, Christophe Morisseau

Entomology

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22 Scopus citations

Abstract

We investigated N-adamantyl-N′-phenyl urea derivatives as simple sEH inhibitors. Salicylate ester derivatives have high inhibitory activities against human sEH, while the free benzoic acids are less active. The methyl salicylate derivative is a potent sEH inhibitor, which also has high metabolic and chemical stabilities; suggesting that such inhibitors are potential lead molecule for bioactive compounds acting in vivo.

Original language	English (US)
Pages (from-to)	1784-1789
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2009.01.069
State	Published - Mar 15 2009

Keywords

Anti-inflammation
Hypertension
Intramolecular hydrogen bond
Metabolic and chemical stability
Salicylate
Soluble epoxide hydrolase
Urea

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

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10.1016/j.bmcl.2009.01.069

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title = "Salicylate-urea-based soluble epoxide hydrolase inhibitors with high metabolic and chemical stabilities",

abstract = "We investigated N-adamantyl-N′-phenyl urea derivatives as simple sEH inhibitors. Salicylate ester derivatives have high inhibitory activities against human sEH, while the free benzoic acids are less active. The methyl salicylate derivative is a potent sEH inhibitor, which also has high metabolic and chemical stabilities; suggesting that such inhibitors are potential lead molecule for bioactive compounds acting in vivo.",

keywords = "Anti-inflammation, Hypertension, Intramolecular hydrogen bond, Metabolic and chemical stability, Salicylate, Soluble epoxide hydrolase, Urea",

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AU - Kasagami, Takeo

AU - Kim, In Hae

AU - Tsai, Hsing Ju

AU - Nishi, Kosuke

AU - Hammock, Bruce D.

AU - Morisseau, Christophe

PY - 2009/3/15

Y1 - 2009/3/15

N2 - We investigated N-adamantyl-N′-phenyl urea derivatives as simple sEH inhibitors. Salicylate ester derivatives have high inhibitory activities against human sEH, while the free benzoic acids are less active. The methyl salicylate derivative is a potent sEH inhibitor, which also has high metabolic and chemical stabilities; suggesting that such inhibitors are potential lead molecule for bioactive compounds acting in vivo.

AB - We investigated N-adamantyl-N′-phenyl urea derivatives as simple sEH inhibitors. Salicylate ester derivatives have high inhibitory activities against human sEH, while the free benzoic acids are less active. The methyl salicylate derivative is a potent sEH inhibitor, which also has high metabolic and chemical stabilities; suggesting that such inhibitors are potential lead molecule for bioactive compounds acting in vivo.

KW - Anti-inflammation

KW - Hypertension

KW - Intramolecular hydrogen bond

KW - Metabolic and chemical stability

KW - Salicylate

KW - Soluble epoxide hydrolase

KW - Urea

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JO - Bioorganic and Medicinal Chemistry Letters

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ER -

Salicylate-urea-based soluble epoxide hydrolase inhibitors with high metabolic and chemical stabilities

Abstract

Keywords

ASJC Scopus subject areas

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