Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 128, Issue -, Pages 319-331Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2017.02.009
Keywords
Hetero annulated carbazoles; Pyrimidocarbazole; Structure-activity relationship; Cytotoxicity; Fluorescent microscopic analysis
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Funding
- UGC-Emeritus fellowship [EMERITUS-2015-17-OBC-7410 (SAII)]
- UGC-RGNF, New Delhi
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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, H-1 NMR, C-13 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. (C) 2017 Elsevier Masson SAS. All rights reserved.
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