Synthesis of hetero annulated isoxazolo-, pyrido- and pyrimido carbazoles: Screened for in vitro antitumor activity and structure activity relationships, a novel 2-amino-4-(3'-bromo-4'-methoxyphenyl)-8-chloro-11H-pyrimido[4,5-a]carbazole as an antitumor agent

Karunanidhi Murali, Hazel A. Sparkes, Karnam Jayarampillai Rajendra Prasad

Research output: Contribution to journalArticle (Academic Journal)peer-review

14 Citations (Scopus)
315 Downloads (Pure)

Abstract

Claisen-Schmidt condensation of 2,3,4,9-tetrahydro-1H-carbazol-1-one with 3-bromo-4-methoxy benzaldehyde afforded the 2-(3'-bromo-4'-methoxybenzylidene)-2,3,4,9-tetrahydro-1H-carbazol-1-one 3. Compound 3 was allowed to react with different organic reactants, hydroxylamine hydrochloride, malononitrile and guanidine nitrate through condensation cum cycloaddition reactions to afford a series of the respective novel hetero annulated carbazoles such as isoxazolo-, pyrido- and pyrimido carbazoles. The structures of the compounds were established by FT-IR, 1H NMR, 13C NMR, X-ray diffraction and elemental analysis. The compounds have been screened for in vitro anti-tumor activity by MTT assay and displayed enviable selective growth inhibition on MCF-7 cell line compared to A-549 cell line. Apoptotic morphological changes in MCF-7 and A-549 cells were visualized using fluorescent microscopic technique. The preliminary structure activity relationships were also carried out. Data pointed out that among pyrimido carbazole compounds, 2-amino-4-(3'-bromo-4'-methoxyphenyl)-8-chloro-11H-pyrimido [4,5-a]carbazole could be exploited as an excellent therapeutic drug against cancer cell proliferation.
Original languageEnglish
Pages (from-to)319-331
Number of pages13
JournalEuropean Journal of Medicinal Chemistry
Volume128
Early online date7 Feb 2017
DOIs
Publication statusPublished - 10 Mar 2017

Keywords

  • Hetero annulated carbazoles
  • Pyrimidocarbazole
  • Structure-activity relationship
  • Cytotoxicity
  • Fluorescent microscopic analysis

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