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Monatshefte für Chemie - Chemical Monthly

, Volume 144, Issue 6, pp 825–849 | Cite as

N′-[4-[(Substituted imino)methyl]benzylidene]-substituted benzohydrazides: synthesis, antimicrobial, antiviral, and anticancer evaluation, and QSAR studies

  • Pradeep Kumar
  • Balasubramanian Narasimhan
  • Kalavathy Ramasamy
  • Vasudevan Mani
  • Rakesh Kumar Mishra
  • Abu Bakar Abdul Majeed
  • Erik De Clercq
Original Paper

Abstract

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.

Graphical Abstract

Keywords

Hydrazides Antimicrobial Antiviral Anticancer QSAR 

Notes

Acknowledgments

The antiviral assays were performed by the Laboratory of Virology and Chemotherapy at the Rega Institute for Medical Research, KU Leuven, Leuven, Belgium.

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Copyright information

© Springer-Verlag Wien 2012

Authors and Affiliations

  • Pradeep Kumar
    • 1
  • Balasubramanian Narasimhan
    • 1
  • Kalavathy Ramasamy
    • 2
  • Vasudevan Mani
    • 3
  • Rakesh Kumar Mishra
    • 3
  • Abu Bakar Abdul Majeed
    • 3
  • Erik De Clercq
    • 4
  1. 1.Faculty of Pharmaceutical SciencesMaharshi Dayanand UniversityRohtakIndia
  2. 2.Collaborative Drug Discovery Research Group, Faculty of Pharmacy, Campus Puncak AlamUniversiti Teknologi MARA (UiTM)Shan AlamMalaysia
  3. 3.Brain Research Laboratory, Faculty of Pharmacy, Campus Puncak AlamUniversiti Teknologi MARA (UiTM)Shan AlamMalaysia
  4. 4.Laboratory of Virology and ChemotherapyRega Institute for Medical ResearchLouvainBelgium

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