Synthesis and anti-tubercular and antimicrobial activities of some 2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one N-isonicotinoylhydrazone derivatives.
In this study, seven 2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one N-isonicotinoylhydrazones 8-14 were synthesized. The structure and stereochemistry of these compounds were established by IR and NMR spectral data. The purities were checked by elemental analysis. The synthesized compounds adopt twin-chair conformation with equatorial orientations of the aryl groups. The compounds were evaluated for their in vitro anti-tubercular and antimicrobial activities. The initial screen was conducted against Mycobacterium tuberculosis H(37)Rv (ATTCC 27294) and INH-TB by luciferase reporter phage assay method. All the synthesized compounds showed very good activity against MTB and INH-TB. Though all the compounds showed good antimicrobial activity only 11 (Ar = p-chlorophenyl), 12 (Ar = p-fluorophenyl), 13 (Ar = m-chlorophenyl) and 14 (Ar = m-methoxyphenyl) exhibited activity against all the tested (bacterial and fungal) microorganisms. The results suggest that the formation of hydrogen bonds may play a significant role in drug action.
Sankar
C
C
Department of Chemistry, Annamalai University, Annamalainagar 608002, Tamilnadu, India.
Pandiarajan
K
K
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared
D000890:Anti-Infective Agents; D000995:Antitubercular Agents; D006835:Hydrazones