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Silica-supported thionyl chloride-assisted synthesis and bioassay of novel tetrazinan-3-thione and 3-oxo-pyrazolidine-4-carbonitrile derivatives of steroids

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Abstract

A series of tetrazinan-3-thione and 3-oxo-pyrazolidine-4-carbonitrile derivatives of steroids(1–3) were synthesized with silica-chloride as a heterogeneous catalyst. The synthesized compounds 4–9 were obtained in substantial yields. In vitro evaluation of anticancer and antioxidant activity of the synthesized compounds was carried out via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide(MTT) and 1,1-diphenyl-2-picrylhydrazyl(DPPH) assays, respectively. Compound 6 exhibited promising anti-proliferative activity towards a panel of cancer cell lines. The significant activity of compound 6 was further ascertained on structural, molecular modelling and docking studies. This study may provide a valuable insight into the further design and development of more potent biologically active compounds.

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Authors and Affiliations

  1. Department of Chemistry, Aligarh Muslim University, Aligarh, 202002, India

    Mehtab Parveen, Ali Mohammed Malla, Akhtar Ali & Mahboob Alam

  2. Department of Biochemistry, Aligarh Muslim University, Aligarh, 202002, India

    Mir Faisal Mustafa

Authors
  1. Mehtab Parveen
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  2. Ali Mohammed Malla
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  3. Akhtar Ali
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  4. Mahboob Alam
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  5. Mir Faisal Mustafa
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Correspondence to Mehtab Parveen.

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Parveen, M., Malla, A.M., Ali, A. et al. Silica-supported thionyl chloride-assisted synthesis and bioassay of novel tetrazinan-3-thione and 3-oxo-pyrazolidine-4-carbonitrile derivatives of steroids. Chem. Res. Chin. Univ. 30, 55–62 (2014). https://doi.org/10.1007/s40242-014-3308-7

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  • DOI: https://doi.org/10.1007/s40242-014-3308-7

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