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3-[4-(甲磺酰基)苯基]-5-(三氟甲基)(2-吡啶基)苯乙酮作为一种强效且口服活性的环氧化酶-2选择性抑制剂：合成与生物学评价

3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone as a potent and orally active cyclooxygenase-2 selective inhibitor: synthesis and biological evaluation.

作者信息

Khanapure Subhash P, Augustyniak Michael E, Earl Richard A, Garvey David S, Letts L Gordon, Martino Allison M, Murty Madhavi G, Schwalb David J, Shumway Matthew J, Trocha Andrzej M, Young Delano V, Zemtseva Irina S, Janero David R

机构信息

NitroMed, Inc., 125 Spring Street, Lexington, Massachusetts 02421, USA.

出版信息

J Med Chem. 2005 Jun 2;48(11):3930-4. doi: 10.1021/jm0582064.

DOI:10.1021/jm0582064
PMID:15916445
Abstract

Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 microM and COX-1 IC50 = 14 microM (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20.

摘要

在中心支架与芳基环之间引入一个间隔基团，得到了一种新的环氧合酶-2（COX-2）选择性抑制剂核心结构，即3-[4-(甲基磺酰基)苯基]-5-(三氟甲基)(2-吡啶基)苯基酮（20），其COX-2半数抑制浓度（IC50）为0.25微摩尔/升，COX-1的IC50为14微摩尔/升（人全血检测）。化合物20在大鼠气囊炎症模型中具有口服活性，可抑制白细胞浸润和COX-2衍生的前列腺素生成。我们的数据支持鉴定以20为代表的新型COX-2选择性抑制剂核心结构。

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