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  3. 5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: Synthesis and evaluation

5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: Synthesis and evaluation

  • Bioorg Med Chem Lett. 2019 Sep 15;29(18):2664-2669. doi: 10.1016/j.bmcl.2019.07.040.
Sandeep Kumar Marvadi 1,  Vagolu Siva Krishna 2,  Ekaterina O Sinegubova 3,  Alexandrina S Volobueva 3,  Yana L Esaulkova 3,  Anna A Muryleva 3,  Dmitry G Tentler 4,  Dharmarajan Sriram 2,  Vladimir V Zarubaev 3,  Srinivas Kantevari 5
Affiliations

Affiliations

  • 1 Fluro and Agrochemicals Division (Organic Chemistry Division-II), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.
  • 2 Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India.
  • 3 Pasteur Institute of Epidemiology and Microbiology, 14 Mira Str., 197101 St. Petersburg, Russian Federation.
  • 4 Institute of Cytology, Russian Academy of Sciences, 4, Tikhorezky Av., 194064, Russian Federation.
  • 5 Fluro and Agrochemicals Division (Organic Chemistry Division-II), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India; Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India. Electronic address: ksrinivas@iict.res.in.
PMID: 31375291 DOI: 10.1016/j.bmcl.2019.07.040
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.

Keywords

Antivirals; Click chemistry; Dihydroquinoline; Influenza virus; Mycobacterium tuberculosis; Thiophene; Triazole.

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