2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder
- Author(s)
- Brown, RN; Cameron, R; Chalmers, DK; Hamilton, S; Luttick, A; Krippner, GY; McConnell, DB; Nearn, R; Stanislawski, PC; Tucker, SP; Watson, KG;
- Details
- Publication Year 2005-04-15,Volume 15,Issue #8,Page 2051-2055
- Journal Title
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Publication Type
- Journal Article
- Abstract
- 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.
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- COMMON COLD; ANTIVIRAL COMPOUNDS; DESIGN; INHIBITORS; EFFICACY; SAFETY; AGENTS
- Publisher's Version
- https://doi.org/10.1016/j.bmcl.2005.02.054
- Terms of Use/Rights Notice
- Refer to copyright notice on published article.
Creation Date: 2005-04-15 12:00:00