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Title: 5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: Synthesis and evaluation
Authors: Marvadi, Sandeep Kumar
Krishna, Vagolu Siva
Sinegubova, Ekaterina O
Volobueva, Alexandrina S
Esaulkova, Yana L
Muryleva, Anna A
Tentler, Dmitry G
Sriram, Dharmarajan
Kantevari, Srinivas
Zarubaev, Vladimir V. 
Keywords: Antivirals;Click chemistry;Dihydroquinoline;Influenza virus;Mycobacterium tuberculosis;Thiophene;Triazole
Issue Date: 15-Sep-2019
Publisher: Elsevier
Journal: Bioorganic and Medicinal Chemistry Letters 
Abstract: This study describes synthesis and evaluation of novel 5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines 7a-o as dual inhibitors of Mycobacterium tuberculosis and influenza virus. Huisgen's [3+2] dipolar cycloaddition of 6-(azidomethyl)-5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline 5 with various alkynes 6a-o using sodium ascorbate and copper sulphate gave new dihydroquinoline-1,2,3-triazoles 7a-o in good to excellent yields. The new compounds were evaluated for in vitro antimycobacterial against M. tuberculosis H37Rv (Mtb) and antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1). Among the fifteen new analogs, compounds 7a (MIC: 3.12 µg/mL), 7j and 7k (MIC: 6.25 µg/mL) were identified as potent antitubercular agents. The virus-inhibiting activity of all the fifteen compounds was found to be moderate, and among them the compound 7l, bearing thiophene moiety appeared the most active with good selectivity index (IC50 = 19.5 µg/mL; SI = 15). The results presented here will help developing newer dual inhibitors of tuberculosis and influenza virus.
ISSN: 0960-894X
DOI: 10.1016/j.bmcl.2019.07.040
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