tetano
Editor, Senior Moderator
Bioorg Med Chem Lett. 2019 Jul 24. pii: S0960-894X(19)30496-2. doi: 10.1016/j.bmcl.2019.07.040. [Epub ahead of print]
[h=1]5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: Synthesis and evaluation.[/h] Marvadi SK[SUP]1[/SUP], Krishna VS[SUP]2[/SUP], Sinegubova EO[SUP]3[/SUP], Volobueva AS[SUP]3[/SUP], Esaulkova YL[SUP]3[/SUP], Muryleva AA[SUP]3[/SUP], Tentler DG[SUP]4[/SUP], Sriram D[SUP]2[/SUP], Zarubaev VV[SUP]3[/SUP], Kantevari S[SUP]5[/SUP].
[h=3]Author information[/h]
[h=3]Abstract[/h] 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 ?g/mL), 7j and 7k (MIC: 6.25 ?g/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 (IC[SUB]50[/SUB] = 19.5 ?g/mL; SI = 15). The results presented here will help developing newer dual inhibitors of tuberculosis and influenza virus.
Copyright ? 2019 Elsevier Ltd. All rights reserved.
[h=4]KEYWORDS:[/h] Antivirals; Click chemistry; Dihydroquinoline; Influenza virus; Mycobacterium tuberculosis; Thiophene; Triazole
PMID: 31375291 DOI: 10.1016/j.bmcl.2019.07.040
[h=1]5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: Synthesis and evaluation.[/h] Marvadi SK[SUP]1[/SUP], Krishna VS[SUP]2[/SUP], Sinegubova EO[SUP]3[/SUP], Volobueva AS[SUP]3[/SUP], Esaulkova YL[SUP]3[/SUP], Muryleva AA[SUP]3[/SUP], Tentler DG[SUP]4[/SUP], Sriram D[SUP]2[/SUP], Zarubaev VV[SUP]3[/SUP], Kantevari S[SUP]5[/SUP].
[h=3]Author information[/h]
[h=3]Abstract[/h] 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 ?g/mL), 7j and 7k (MIC: 6.25 ?g/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 (IC[SUB]50[/SUB] = 19.5 ?g/mL; SI = 15). The results presented here will help developing newer dual inhibitors of tuberculosis and influenza virus.
Copyright ? 2019 Elsevier Ltd. All rights reserved.
[h=4]KEYWORDS:[/h] Antivirals; Click chemistry; Dihydroquinoline; Influenza virus; Mycobacterium tuberculosis; Thiophene; Triazole
PMID: 31375291 DOI: 10.1016/j.bmcl.2019.07.040