The novel benzopyran class of selective cyclooxygenase-2 inhibitors-part I: The first clinical candidate

Jane L. Wang; Jeffery Carter; James R. Kiefer; Ravi G. Kurumbail; Jennifer L. Pawlitz; David Brown; Susan J. Hartmann; Matthew J. Graneto; Karen Seibert; John J. Talley

doi:10.1016/j.bmcl.2010.07.053

The novel benzopyran class of selective cyclooxygenase-2 inhibitors-part I: The first clinical candidate

Jane L. Wang, Jeffery Carter, James R. Kiefer, Ravi G. Kurumbail, Jennifer L. Pawlitz, David Brown, Susan J. Hartmann, Matthew J. Graneto, Karen Seibert, John J. Talley

Department of Anesthesiology

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

37 Scopus citations

Abstract

In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. 5c-(S) (SD-8381) was advanced into clinical studies due to its superior in vivo potency. The high plasma protein binding (>99% bound) of 5c-(S) has resulted in a surprisingly long human half life t_1/2 = 360 h.

Original language	English
Pages (from-to)	7155-7158
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2010.07.053
State	Published - Dec 1 2010

Keywords

Benzopyran
COX-2 inhibitor
Clinical candidate
Cyclooxygenase
Half-life
Plasma protein bound
X-ray crystal structure

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10.1016/j.bmcl.2010.07.053

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title = "The novel benzopyran class of selective cyclooxygenase-2 inhibitors-part I: The first clinical candidate",

abstract = "In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. 5c-(S) (SD-8381) was advanced into clinical studies due to its superior in vivo potency. The high plasma protein binding (>99% bound) of 5c-(S) has resulted in a surprisingly long human half life t1/2 = 360 h.",

keywords = "Benzopyran, COX-2 inhibitor, Clinical candidate, Cyclooxygenase, Half-life, Plasma protein bound, X-ray crystal structure",

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T1 - The novel benzopyran class of selective cyclooxygenase-2 inhibitors-part I

T2 - The first clinical candidate

AU - Wang, Jane L.

AU - Carter, Jeffery

AU - Kiefer, James R.

AU - Kurumbail, Ravi G.

AU - Pawlitz, Jennifer L.

AU - Brown, David

AU - Hartmann, Susan J.

AU - Graneto, Matthew J.

AU - Seibert, Karen

AU - Talley, John J.

PY - 2010/12/1

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AB - In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. 5c-(S) (SD-8381) was advanced into clinical studies due to its superior in vivo potency. The high plasma protein binding (>99% bound) of 5c-(S) has resulted in a surprisingly long human half life t1/2 = 360 h.

KW - Benzopyran

KW - COX-2 inhibitor

KW - Clinical candidate

KW - Cyclooxygenase

KW - Half-life

KW - Plasma protein bound

KW - X-ray crystal structure

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SN - 0960-894X

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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ER -

The novel benzopyran class of selective cyclooxygenase-2 inhibitors-part I: The first clinical candidate

Abstract

Keywords

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