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

Medicinal Chemistry Research volume 22, pages 1957–1971 (2013)Cite this article

Abstract

In this study, N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides (1–26) 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.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, 124001, India

    Harsh Kumar, Pradeep Kumar & Balasubramanian Narasimhan

  2. Collaborative Drug Discovery Research Group, Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Campus Puncak Alam, 42300, Bandar Puncak Alam, Selangor, Malaysia

    Kalavathy Ramasamy

  3. Brain Research Laboratory, Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Campus Puncak Alam, 42300, Bandar Puncak Alam, Selangor, Malaysia

    Vasudevan Mani, Rakesh Kumar Mishra & Abu Bakar Abdul Majeed

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  1. Harsh Kumar
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  2. Pradeep Kumar
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  3. Balasubramanian Narasimhan
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Correspondence to Balasubramanian Narasimhan.

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Kumar, H., Kumar, P., Narasimhan, B. et al. Synthesis, in vitro antimicrobial, antiproliferative, and QSAR studies of N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides. Med Chem Res 22, 1957–1971 (2013). https://doi.org/10.1007/s00044-012-0181-0

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  • DOI: https://doi.org/10.1007/s00044-012-0181-0

Keywords

  • Benzamides
  • QSAR
  • Antimicrobial
  • Antiproliferative