An orally bioavailable oxime ether capsid binder with potent activity against human rhinovirus

J Med Chem. 2003 Jul 17;46(15):3181-4. doi: 10.1021/jm0202876.

Keith G Watson ¹, Renee N Brown, Rachel Cameron, David K Chalmers, Stephanie Hamilton, Betty Jin, Guy Y Krippner, Angela Luttick, Darryl B McConnell, Phillip A Reece, Jane Ryan, Pauline C Stanislawski, Simon P Tucker, Wen-Yang Wu, Dale L Barnard, Robert W Sidwell

Affiliations

Affiliation

1 Biota Chemistry Laboratory, School of Chemistry, Monash University, PO Box 23 Victoria, Australia 3800. [email protected]

PMID: 12852746 DOI: 10.1021/jm0202876

Abstract

A series of capsid-binding compounds was screened against human rhinovirus (HRV) using a CPE based assay. The ethyl oxime ether 14 was found to have outstanding anti-HRV activity (median IC(50) 4.75 ng/mL), and unlike the equivalent ethyl ester compound 3 (Pirodavir), it has good oral bioavailability, making it a promising development candidate. Compound 14 illustrates that an oxime ether group can act as a metabolically stable bioisostere for an ester functionality.

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