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Synthesis and cellular cytotoxicities of new N-substituted indole-3-carbaldehyde and their indolylchalcones

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Abstract

A simple and efficient method for N-alkylation of indole-3-carbaldehyde derivatives using a mixture of different bases in DMF under conventional and microwave irradiation conditions to afford N-substituted indole-3-carbaldehyde derivatives 3a–o is reported. These derivatives which undergo Claisen-Schmidt condensation with 1-biphenyl-4-yl-ethanone yielded the corresponding indolylchalcone derivatives 5a–h. A comparative study showed that the microwave irradiation condition afforded excellent yield and shorten reaction time of all the synthesized indole derivatives which possess promising antitumor activity as well as interchelation bioactivity of indolylchalcones 5a–h with DNA.

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Authors and Affiliations

  1. Organic Chemistry Laboratory, Department of Chemistry, Faculty of Science, Menoufiya University, Menoufiya, 32511, Egypt

    Magdy A. H. Zahran

  2. Department of Microbiology and Biotechnology, Genetic Engineering and Biotechnology Institute, Menoufiya University, Menoufiya, 32511, Egypt

    Atef M. Ibrahim

Authors
  1. Magdy A. H. Zahran
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  2. Atef M. Ibrahim
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Correspondence to Magdy A. H. Zahran.

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Zahran, M.A.H., Ibrahim, A.M. Synthesis and cellular cytotoxicities of new N-substituted indole-3-carbaldehyde and their indolylchalcones. J Chem Sci 121, 455–462 (2009). https://doi.org/10.1007/s12039-009-0054-3

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  • DOI: https://doi.org/10.1007/s12039-009-0054-3

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