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

43 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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doi = "10.1016/j.bmcl.2010.07.053",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

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

Y1 - 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

UR - https://www.scopus.com/pages/publications/78149260251

U2 - 10.1016/j.bmcl.2010.07.053

DO - 10.1016/j.bmcl.2010.07.053

M3 - Article

C2 - 21055613

AN - SCOPUS:78149260251

SN - 0960-894X

VL - 20

SP - 7155

EP - 7158

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

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

Abstract

Keywords

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