Medicinal Chemistry Research

, Volume 26, Issue 10, pp 2243–2259 | Cite as

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

  • Pedavenkatagari Narayana Reddy
  • Pannala Padmaja
  • Bobbala Ramana Reddy
  • Surender Singh Jadav
Original Research

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.

Keywords

Mannich bases 4-Hydroxycarbazole Ortho-quinone methide Pyrano[3,2-c]carbazoles Antioxidant activity Molecular docking 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

44_2017_1927_MOESM1_ESM.docx (3 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Pedavenkatagari Narayana Reddy
    • 1
  • Pannala Padmaja
    • 2
  • Bobbala Ramana Reddy
    • 1
  • Surender Singh Jadav
    • 3
  1. 1.Department of Chemistry, Gitam School of TechnologyGitam UniversityHyderabadIndia
  2. 2.Department of ChemistryJNTUH College of EngineeringHyderabadIndia
  3. 3.Department of Pharmaceutical Sciences & TechnologyBirla Institute of TechnologyRanchiIndia

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