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Design, synthesis, antimicrobial, anticancer evaluation, and QSAR studies of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones

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Abstract

A series of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones (1–17) was synthesized and tested in vitro for its antimicrobial and anticancer potentials. The biological screening results indicated that compounds having m-chloro substituent on benzaldehyde portion showed antimicrobial potential, whereas compounds having chloro, methoxy, and hydroxyl groups showed anticancer potential. The quantitative structure activity relationship (QSAR) studies indicated the importance of topological parameter, valence first order molecular connectivity index in describing antifungal activity. The developed QSAR models, however, were statistically insignificant with reference to anticancer activity of the synthesized compounds.

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Authors and Affiliations

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

    Sumit Sigroha, Balasubramanian Narasimhan, Pradeep Kumar & Anurag Khatkar

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

    Kalavathy Ramasamy

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

    Vasudevan Mani, Rakesh Kumar Mishra & Abu Bakar Abdul Majeed

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  1. Sumit Sigroha
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  2. Balasubramanian Narasimhan
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Correspondence to Balasubramanian Narasimhan.

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Sigroha, S., Narasimhan, B., Kumar, P. et al. Design, synthesis, antimicrobial, anticancer evaluation, and QSAR studies of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones. Med Chem Res 21, 3863–3875 (2012). https://doi.org/10.1007/s00044-011-9906-8

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