Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents

European Journal of Medicinal Chemistry
Debasish BandyopadhyayBimal K Banik

Abstract

A series of novel N-substituted pyrrole derivatives have been designed and synthesized following ultrasound-assisted and bismuth nitrate-catalyzed eco-friendly route. This reaction has also provided a general method to prepare diverse varieties of N-substituted pyrroles with less nucleophilic polyaromatic amines. Based on (1)H NMR spectroscopy, a plausible mechanistic pathway has been advanced. Cytotoxicity of some selected N-substituted pyrrole derivatives has been evaluated in vitro in a panel of mammalian cancer cell lines which includes liver cancer cell lines (HepG2 and Hepa1-6), colon cancer cell lines (HT-29 and Caco-2), a cervical cancer cell line (HeLa) and NIH3T3 cells. Two compounds, 5-(1H-pyrrol-1-yl)-1,10-phenanthroline (9) and 1-(phenanthren-2-yl)-1H-pyrrole (10) have shown good cytotoxicity against some cancer cell lines. Furthermore, these compounds have exhibited cytotoxic specificity against liver cancer cell lines in vitro when compared with normal cultured primary hepatocytes.

References

Dec 28, 2002·Journal of Medicinal Chemistry·Indrani BanikBimal K Banik
Apr 5, 2007·Nature Protocols·Vanicha Vichai, Kanyawim Kirtikara
Dec 7, 2007·Journal of Medicinal Chemistry·Keiichiro OharaJean-Jacques Vasseur
Dec 22, 2007·Chemical Reviews·Hui FanJin-Feng Hu
Apr 24, 2009·Chemical Reviews·Nuno R CandeiasAlexandre F Trindade
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Debasish BandyopadhyayBimal K Banik
Apr 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Debasish BandyopadhyayBimal K Banik
Jul 6, 2010·Chemical Society Reviews·Verónica EstévezJ Carlos Menéndez
Aug 13, 2010·European Journal of Medicinal Chemistry·Bimal K Banik, Frederick F Becker
Oct 29, 2010·Organic Letters·Magnus Rueping, Alejandro Parra

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Citations

Dec 3, 2014·European Journal of Medicinal Chemistry·Debasish BandyopadhyayBimal K Banik
Nov 10, 2015·Organic and Medicinal Chemistry Letters·Debasish BandyopadhyayBimal K Banik
Oct 2, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Debasish BandyopadhyayBimal K Banik Banik
Nov 12, 2013·Archiv der Pharmazie·Nabhubygari Mahaboob BashaTartte Vijaya

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