Anti-influenza Virus Activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides

Bioorganic & Medicinal Chemistry Letters
2001.0

Abstract

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-isoxazolin-3-ylmethyl)acetamide (1j) was the most active inhibitor with an EC(50) of 3 microg/mL in vitro.

Knowledge Graph

Similar Paper

Anti-influenza Virus Activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides
Bioorganic & Medicinal Chemistry Letters 2001.0
Synthesis and anti-influenza activities of carboxyl alkoxyalkyl esters of 4-guanidino-Neu5Ac2en (zanamivir)
Bioorganic & Medicinal Chemistry Letters 2007.0
Design, synthesis and anti-influenza A virus activity of novel 2,4-disubstituted quinazoline derivatives
Bioorganic & Medicinal Chemistry Letters 2020.0
Aliphatic and alicyclic camphor imines as effective inhibitors of influenza virus H1N1
European Journal of Medicinal Chemistry 2017.0
Synthesis and antiviral activity of substituted bisaryl amide compounds as novel influenza virus inhibitors
European Journal of Medicinal Chemistry 2012.0
An Evaluation of the Antirhinoviral Activity of Acylfuran Replacements for 3-Methylisoxazoles. Are 2-Acetylfurans Bioisosteres for 3-Methylisoxazoles?
Journal of Medicinal Chemistry 1994.0
1,2,3-Triazolyl-4-oxoquinolines: A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses
Bioorganic & Medicinal Chemistry 2015.0
The semi-synthesis of novel andrographolide analogues and anti-influenza virus activity evaluation of their derivatives
Bioorganic & Medicinal Chemistry Letters 2016.0
Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling
Bioorganic & Medicinal Chemistry Letters 1999.0
Design, synthesis and in vitro anti-influenza A virus evaluation of novel quinazoline derivatives containing S-acetamide and NH-acetamide moieties at C-4
European Journal of Medicinal Chemistry 2020.0