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Medicinal Chemistry Research

, Volume 22, Issue 4, pp 1957–1971 | Cite as

Synthesis, in vitro antimicrobial, antiproliferative, and QSAR studies of N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides

  • Harsh Kumar
  • Pradeep Kumar
  • Balasubramanian Narasimhan
  • Kalavathy Ramasamy
  • Vasudevan Mani
  • Rakesh Kumar Mishra
  • Abu Bakar Abdul Majeed
Original Research

Abstract

In this study, N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides (126) were synthesized and screened for their in vitro antibacterial (Gram positive; S. aureus, B. subtilis and Gram negative; E. coli) and antifungal (C. albicans and A. niger) activities. The antimicrobial activity results indicated that compound, 4-(1H-indol-3-ylazo)-N-(4-nitro-phenyl)-benzamide (12, pMICam = 1.61) was the most potent. In general, it was found that the synthesized compounds were bacteriostatic/fungistatic in action except fungicidal for A. niger. The synthesized compounds were also evaluated for their antiproliferative activity against human colon cancer (HCT116), murine leukemia (P388), and breast cancer (MCF7) cell lines. The antiproliferative study results demonstrated 4-(1H-indol-3-ylazo)-N-p-tolyl-benzamide (2, IC50 = 0.0003 μM/mL) and 4-(1H-indol-3-ylazo)-N-p-tolyl-benzamide (21, 0.0003 μM/mL) as lead compounds for the development of novel antiproliferative agents. The QSAR studies indicated the importance of topological parameters, Kier’s alpha second-order shape indice (κα2) and Wiener index (W) in describing the antimicrobial activity of the synthesized compounds.

Keywords

Benzamides QSAR Antimicrobial Antiproliferative 

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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Harsh Kumar
    • 1
  • Pradeep Kumar
    • 1
  • Balasubramanian Narasimhan
    • 1
  • Kalavathy Ramasamy
    • 2
  • Vasudevan Mani
    • 3
  • Rakesh Kumar Mishra
    • 3
  • Abu Bakar Abdul Majeed
    • 3
  1. 1.Faculty of Pharmaceutical SciencesMaharshi Dayanand UniversityRohtakIndia
  2. 2.Collaborative Drug Discovery Research Group, Faculty of PharmacyUniversiti Teknologi MARA (UiTM)Bandar Puncak AlamMalaysia
  3. 3.Brain Research Laboratory, Faculty of PharmacyUniversiti Teknologi MARA (UiTM)Bandar Puncak AlamMalaysia

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