2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder

被引：73

作者：

Brown, RN ^{[1
]}

Cameron, R ^{[1
]}

Chalmers, DK ^{[1
]}

Hamilton, S ^{[1
]}

Luttick, A ^{[1
]}

Krippner, GY ^{[1
]}

McConnell, DB ^{[1
]}

Nearn, R ^{[1
]}

Stanislawski, PC ^{[1
]}

Tucker, SP ^{[1
]}

Watson, KG ^{[1
]}

机构：

[1] Biota Holdings, Notting Hill, Vic 3168, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 08期

关键词：

bioisostere; benzoxazole; rhinovirus; HRV; antiviral;

D O I：

10.1016/j.bmcl.2005.02.054

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of pyridazinylpiperidinyl capsid-binding compounds with novel bicyclic substituents were synthesized and screened against human rhinovirus (HRV). Several 2-alkoxy- and 2-alkylthio-benzoxazole and benzothiazole derivatives showed excellent anti-HRV activity. When tested against a panel of 16 representative HRV types the 2-ethoxybenzoxazole derivative 13 was found to have superior HRV activity (median EC50 3.88 ng/mL) to known capsid-binders Pleconaril and Pirodavir. Compound 13 illustrates that a 2-alkoxybenzoxazole group can be an effective bioisostere for a benzoate ester or benzaldehyde oxime ether functionality. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2051 / 2055

页数：5

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