N′-[4-[(Substituted imino)methyl]benzylidene]-substituted benzohydrazides: synthesis, antimicrobial, antiviral, and anticancer evaluation, and QSAR studies
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A variety of N′-[4-[(substituted imino)methyl]benzylidene]-substituted benzohydrazides have been synthesized and evaluated for antimicrobial and anticancer potential. Results from testing of antimicrobial activity indicated the most potent antimicrobial agents had pMIC am = 1.51. The synthesized compounds were bacteriostatic and fungistatic in action. Results from evaluation of antiviral activity indicated that none of the synthesized hydrazide derivatives inhibited viral replication at sub-toxic concentrations. Results from anti-HIV screening against HIV-2 strain ROD indicated that one compound was more potent (IC 50 ≥ 1 μg/cm3) than the standard drug nevirapine (IC 50 ≥ 4 μg/cm3) and another was equipotent (IC 50 ≥ 4 μg/cm3). The most effective anticancer agent against both HCT116 and MCF7 cancer cell lines had IC 50 = 19 and 18 μg/cm3, respectively. QSAR analysis indicated the importance of Wiener index (W) and energy of the lowest unoccupied molecular orbital (LUMO) in describing the antimicrobial activity of the synthesized compounds.
KeywordsHydrazides Antimicrobial Antiviral Anticancer QSAR
The antiviral assays were performed by the Laboratory of Virology and Chemotherapy at the Rega Institute for Medical Research, KU Leuven, Leuven, Belgium.
- 19.Cappucino JG, Sherman N (1999) Microbiology—a laboratory manual. Addison Wesley, Menlo Park, p 263Google Scholar
- 27.Kier LB, Hall LH (1976) Molecular connectivity in chemistry and drug research. Academic Press, New YorkGoogle Scholar
- 29.Randic M (1993) Croat Chem Acta 66:289Google Scholar
- 39.Kier LB, Hall LH (1999) In: Devillers J, Balaban AT (eds) Topological indices and related descriptors in QSAR and QSPR. Gordon and Breach Science Publishers, Amsterdam, p 455Google Scholar
- 40.Kumar P, Narasimhan B, Sharma D (2008) Arkivoc (xiii):159Google Scholar
- 41.Bajaj S, Sambi SS, Madan AK (2005) Croat Chem Acta 78:165Google Scholar
- 43.Pharmacopoeia of India (2007) vol. I. Controller of Publications, Ministry of Health Department, Govt. Of India, New Delhi, p 37Google Scholar
- 45.Hyperchem 6.0 (1993) Hypercube, Inc., FloridaGoogle Scholar
- 46.SPSS for windows version 10.05 (1999) SPSS Inc., BangaloreGoogle Scholar
- 47.TSAR 3D Version 3.3 (2000) Oxford Molecular LimitedGoogle Scholar