1. Synthesis and antiviral activity of 2‐substituted 4‐aminoquinoline and its analogous derivatives.
- Author
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Chirra, Nagaraju, Udigala, Govinda, Sinegubova, Ekaterina O., Nagineni, Devendra, Bollikanda, Rakesh Kumar, Esaulkova, Yana L., Muryleva, Anna A., Zarubaev, Vladimir V., and Kantevari, Srinivas
- Subjects
TRANSITION metal catalysts ,STRUCTURAL optimization ,QUINAZOLINONES ,ACETOPHENONE ,INFLUENZA viruses ,ANNULATION - Abstract
Herein we describe an efficient Lewis acid‐mediated one‐pot synthesis of 2‐substituted 4‐aminoquinolines from commercially available anthranilonitriles and substituted acetophenones via a Friedlander type annulation reaction. The protocol avoids any transition metal catalysts, has a wide substrate scope, and exclusively produces 4‐aminoquinolines in excellent yields. Screening of all the new compounds for in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells revealed nine analogues with good virus‐inhibiting activity and a favorable toxicity profile. Among them, two compounds, 3a (IC50: 1.7 μM, SI = 30) and 3l (IC50: 4.0 μM, SI = 25) with higher potency are the best anti‐influenza hit analogues for further structural optimization. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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