Facile synthesis of benzonitrile/nicotinonitrile based s-triazines as new potential antimycobacterial agents.
A common strategy to synthesize 4/6-(4-(4-methylpiperazin-1-yl)-6-(4-(4-oxo-2-phenylthiazolidin-3-yl)phenyl)-1,3,5-triazin-2-yloxy)benzonitriles/nicotinonitriles was developed by applying an efficient palladium-catalyzed C-C Suzuki coupling. Moreover, the synthesized compounds were also tested for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv using BACTEC MGIT and Lowenstein-Jensen MIC methods. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian cells. The best results were observed amongst the nicotinonitrile substituted s-triazine analogs and it could be a potential starting point to develop new lead compounds in the ﬁght against M. tuberculosis H37Rv. The newly synthesized compounds were characterized by IR, (1)H NMR, (13)C NMR, MS and elemental analysis.
Department of Applied Chemistry, S. V. National Institute of Technology, Surat 395007, India.
Amit B
AB
Patel
Department of Chemistry, School of Science, Gujarat University, Ahmedabad 380009, India. Electronic address: chikhalia_kh@yahoo.com.
Kishor H
KH
Chikhalia
Department of Applied Chemistry, S. V. National Institute of Technology, Surat 395007, India. Electronic address: premlatakumari1@gmail.com.
Premlata
P
Kumari
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D009539:Nicotinic Acids / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D009539:Nicotinic Acids; D009570:Nitriles; D014227:Triazines; C014356:benzonitrile
Antimycobacterial activity; Palladium-catalyzed; Thiazolidin-4-one; s-Triazine