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Synthesis and anticancer activity study of indolyl hydrazide–hydrazones

Medicinal Chemistry Research volume 25, pages 941–950 (2016)Cite this article

Abstract

A series of N′-((1-(substituted)-1H-indol-3-yl)methylene)hydrazides were synthesized and evaluated for their in vitro antiproliferative activities against various cancer cell lines. Formation of indole hydrazide–hydrazones was accomplished by the reaction of indole 3-carboxaldehyde with aryl/alkyl hydrazides in the presence of acetic acid. Out of synthesized twenty-two compounds, some of the analogs exhibited specificity toward breast (18b, 18d, 18f and 18j) and prostate (18t and 18v) cancer cells. Among the prepared derivatives, compounds 18b, 18d and 18j were most cytotoxic (IC50 = 0.9, 0.4 and 0.8 µM, respectively) against the screened cancer cell lines. Exposure of PC3 cells to either 18d or 18j resulted in increased levels of cleaved PARP1, indicating that indolyl hydrazide–hydrazones induce apoptosis in PC3 cells.

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Acknowledgments

We are grateful to CSIR and UGC, New Delhi, for financial support to perform the research work. This work was performed during the association of Swapna Sundaree and Buchi Reddy Vaddula with Birla Institute of Technology and Science, Pilani, India.

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Authors and Affiliations

  1. Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan, 333031, India

    Swapna Sundaree, Mukund P. Tantak, Santosh B. Khandagale & Dalip Kumar

  2. Sustainable Technology Division, National Risk Management Research Laboratory, U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 483, Cincinnati, OH, 45268, USA

    Buchi Reddy Vaddula

  3. Department of Chemistry and Purdue Cancer Center, Purdue University, 560 Oval Drive, West Lafayette, IN, 47907, USA

    Chun Shi & Kavita Shah

Authors
  1. Swapna Sundaree
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  2. Buchi Reddy Vaddula
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  3. Mukund P. Tantak
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  4. Santosh B. Khandagale
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  5. Chun Shi
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  6. Kavita Shah
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  7. Dalip Kumar
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Correspondence to Kavita Shah or Dalip Kumar.

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Sundaree, S., Vaddula, B.R., Tantak, M.P. et al. Synthesis and anticancer activity study of indolyl hydrazide–hydrazones. Med Chem Res 25, 941–950 (2016). https://doi.org/10.1007/s00044-016-1522-1

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  • DOI: https://doi.org/10.1007/s00044-016-1522-1

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