Swamy B Narayana, Suma T K, Rao G Venkateswara, Reddy G Chandrasekara
Vittal Mallya Scientific Research Foundation, P.O. Box 406, K. R. Road, Bangalore 560 004, Karnataka, India.
Eur J Med Chem. 2007 Mar;42(3):420-4. doi: 10.1016/j.ejmech.2006.09.009. Epub 2006 Nov 15.
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.
异烟酰腙是由天然产物腰果壳液的主要成分漆树酸合成的。漆树酸及其5-硝基衍生物中的不饱和侧链通过氧化裂解转化为C(8')-醛。然后将C(8')-醛与异烟肼（一种抗结核药物）偶联，得到N-异烟酰基-N'-8-[(2'-羧基羟基-3'-羟基)苯基]辛醛腙(5)和N-异烟酰基-N'-8-[(2'-羧基羟基-3'-羟基-6-硝基)苯基]辛醛腙(6)。这些漆树醛的异烟酰腙对耻垢分枝杆菌mc(2)155显示出强大的抗分枝杆菌活性。5和6与异烟肼的协同研究显示出比单独使用异烟肼更强的抑制活性。化合物5和6对结核分枝杆菌H(37)Rv也有活性。
