Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis.
Isonicotinoylhydrazones were synthesized from a natural product anacardic acid, a major constituent of cashew nut shell liquid. The unsaturated side chain in anacardic acid and its 5-nitro derivative were converted into C(8')-aldehydes by oxidative cleavage. C(8')-aldehydes are then coupled with isoniazid (an anti-TB drug) to obtain N-isonicotinoyl-N'-8-[(2'-carbohydroxy-3'-hydroxy) phenyl] octanal hydrazone (5) and N-isonicotinoyl-N'-8-[(2'-carbohydroxy-3'-hydroxy-6-nitro) phenyl] octanal hydrazone (6). These isonicotinoylhydrazones of anacardic aldehydes showed potent antimycobacterial activity against Mycobacterium smegmatis mc(2)155. The synergistic studies of 5 and 6 with isoniazid showed more inhibitory activities than isoniazid alone. Compounds 5 and 6 also showed activity against Mycobacterium tuberculosis H(37)Rv.
Swamy
B Narayana
BN
Vittal Mallya Scientific Research Foundation, P.O. Box 406, K. R. Road, Bangalore 560 004, Karnataka, India.
Suma
T K
TK
Rao
G Venkateswara
GV
Reddy
G Chandrasekara
GC
D048729:Anacardic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D004357:Drug Synergism; D007538:Isoniazid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D020102:Mycobacterium smegmatis / Q000187:drug effects*; D013056:Spectrophotometry, Ultraviolet
D048729:Anacardic Acids; D000900:Anti-Bacterial Agents; D000995:Antitubercular Agents; C088115:anacardic acid; D007538:Isoniazid