Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 11, Issue 15, Pages 1997-2000Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0960-894X(01)00362-6
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A series of 2-alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides and related compounds were synthesized and their antiviral activities against human influenza A virus were assessed. Studies of the structure-activity relationships revealed the strongest antiviral activity when position-5 of the isoxazoline ring was substituted with a tert-butyl group. When the alkoxyimino moiety was substituted with a methyl, ethyl, isopropyl or allyl group, good antiviral activity was obtained. Among the geometrical isomers at the oxime moiety, the E-isomers were more active than the Z-isomers. Among the compounds examined, (E)-2-allyloxyimino-2-cyano-N-(5-tert-butyl-2-iosaxazolin-3-ylmethyl)acetamide (1j) was the most active inhibitor with an EC50 of 3 mug/mL in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.
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