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Multistep synthesis of 1-[{(5-alkenyl/hydroxyalkenylsubstituted)-1,3,4-oxadiazol-2-yl}-methyl]-2-methyl-1H-benzimidazole series and in vitro anticancer screening, SAR studies

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Abstract

A novel series of hydroxy and non-hydroxy long chain substituted 1,3,4-oxadiazole moiety bearing 2-methyl-1H-benzimidazoles 15(a–d) have been synthesized from cyclization reaction of 2-(2-methyl-1H-benzimidazol-1-yl) acetohydrazide (13) with different unsaturated hydroxy and non-hydroxy fatty esters in the presence of phosphorus oxychloride and product obtained in appreciable yield. Compound (13) was synthesized from the corresponding ethyl (2-methyl-1H-benzimidazol-1-yl) acetate (12) and 2-methyl-1H-benzimidazole (11). All the synthesized compounds were characterized with the help of IR, 1H NMR, 13C NMR, and mass spectral studies. These compounds were tested for cytotoxic (or antiproliferative) activity against normal human blood cells (PBMCs), Hep3B (human hepatocellular carcinoma), MCF 7 (human breast adenocarcinoma), and HeLa (human cervical carcinoma) cell lines.

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Abbreviations

SAR studies:

Structure activity relationship studies

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Acknowledgments

The authors are thankful to the Department of Chemistry, Aligarh Muslim University, Aligarh for providing the necessary research facility. Two of the authors namely (HV)1 and (AA)1 are thankful to DST and CSIR New Delhi for the award of SRF. We are also grateful to the SAIF, Punjab University, Chandigarh for providing spectral technique. In part the research is also supported by UGC-SAP (DRS-I).

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Authors and Affiliations

  1. Department of Chemistry, Aligarh Muslim University, Aligarh, 202 002, India

    Himani Varshney, Aiman Ahmad & Abdul Rauf

  2. Interdisciplinary Biotechnology Unit, Aligarh Muslim University, Aligarh, 202 002, India

    Asif Sherwani & Mohammad Owais

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  1. Himani Varshney
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  2. Aiman Ahmad
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  3. Abdul Rauf
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  4. Asif Sherwani
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  5. Mohammad Owais
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Correspondence to Abdul Rauf.

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Varshney, H., Ahmad, A., Rauf, A. et al. Multistep synthesis of 1-[{(5-alkenyl/hydroxyalkenylsubstituted)-1,3,4-oxadiazol-2-yl}-methyl]-2-methyl-1H-benzimidazole series and in vitro anticancer screening, SAR studies. Med Chem Res 24, 944–953 (2015). https://doi.org/10.1007/s00044-014-1162-2

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