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Synthesis of novel 1,2,3-triazole tethered 1,3-disubstituted β-carboline derivatives and their cytotoxic and antibacterial activities

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Abstract

In this paper new β-carboline derivatives possessing the 1,2,3-triazole ring at C-1 substituent were synthesized from L-tryptophan by Pictet–Spengler reaction followed by a Huisgen 1,3-dipolar addition. In vitro cytotoxicity and antibacterial activity of synthetic compounds were investigated. Methyl 1-(3-((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-β-carboline-3-carboxylate (7f) showed the highest cytotoxic activity with IC50 values of 46 and 32 μM against Hela and HepG2 cell lines, respectively. Compounds 7d and 7i (possessing 4-bromophenyl substituent) and 5c showed excellent inhibition activity for Enterococcus faecium with MIC of 8 μg/mL. The results demonstrated that the presence of 1,2,3-triazole rings in β-carboline derivatives improve their biological activities.

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Authors and Affiliations

  1. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113, Tehran, Iran

    Peyman Salehi, Kosar Babanezhad-Harikandei & Morteza Bararjanian

  2. UoN Chair of Oman’s Medicinal Plants and Marine Natural Products, University of Nizwa, P.O Box 33, Birkat Al Mauz, Nizwa, Postal Code 616, Oman

    Ahmed Al-Harrasi

  3. Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113, Tehran, Iran

    Mohammad-Ali Esmaeili & Atousa Aliahmadi

Authors
  1. Peyman Salehi
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  2. Kosar Babanezhad-Harikandei
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  3. Morteza Bararjanian
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  4. Ahmed Al-Harrasi
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  5. Mohammad-Ali Esmaeili
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  6. Atousa Aliahmadi
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Correspondence to Peyman Salehi.

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Salehi, P., Babanezhad-Harikandei, K., Bararjanian, M. et al. Synthesis of novel 1,2,3-triazole tethered 1,3-disubstituted β-carboline derivatives and their cytotoxic and antibacterial activities. Med Chem Res 25, 1895–1907 (2016). https://doi.org/10.1007/s00044-016-1622-y

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  • DOI: https://doi.org/10.1007/s00044-016-1622-y

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