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Synthesis, in vitro antiproliferative activity, antioxidant activity and molecular modeling studies of new carbazole Mannich bases

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Abstract

A new class of carbazole Mannich bases were synthesized from 4-hydroxycarbazole by reacting with aromatic aldehydes and cyclic amines under mild reaction conditions in good yields. The method does not require column chromatographic purification for isolation of the products. The synthetic potential of these carbazole Mannich bases is exemplified by the ortho-quinone methide formation and subsequent in situ trapping with active methylene compounds bearing a cyano group to construct biologically active pyrano[3,2-c]carbazoles. Further, all the synthesized Mannich bases were tested for their in vitro antiproliferative activity against three cancer cell lines (Hela, MDA-MB-231, and HepG2). The results indicated that these compounds showed selective cytotoxicity against Hela cells. In addition, the synthesized carbazole Mannich bases were also screened for their scavenging activity of the 2,2-diphenyl-1-picrylhydrazyl radical and most of the compounds showed very good antioxidant activity. In silico molecular docking study of synthesized carbazole Mannich bases against colchicine binding site of the tubulin polymer was investigated.

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Acknowledgements

P. Narayana Reddy thanks to DST-SERB, India for a Start-Up Research Grant., P. Padmaja thankful to DST, India for Inspire Faculty Fellowship.

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  1. Department of Chemistry, Gitam School of Technology, Gitam University, Hyderabad, TS, 502 102, India

    Pedavenkatagari Narayana Reddy & Bobbala Ramana Reddy

  2. Department of Chemistry, JNTUH College of Engineering, Kukatpally, Hyderabad, TS, 500 085, India

    Pannala Padmaja

  3. Department of Pharmaceutical Sciences & Technology, Birla Institute of Technology, Ranchi, India

    Surender Singh Jadav

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  1. Pedavenkatagari Narayana Reddy
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Narayana Reddy, P., Padmaja, P., Ramana Reddy, B. et al. Synthesis, in vitro antiproliferative activity, antioxidant activity and molecular modeling studies of new carbazole Mannich bases. Med Chem Res 26, 2243–2259 (2017). https://doi.org/10.1007/s00044-017-1927-5

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