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Issue 23, 2007
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Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties

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Abstract

A multicomponent reaction of indane-1,3-dione, an aldehyde and an amine-containing aromatic compound leading to the formation of indenopyridine-based heterocyclic medicinal scaffolds has been investigated. It was found that the yields significantly improve when oxygen gas is bubbled through the reaction mixture, facilitating the oxidation of the intermediate dihydropyridine-containing compounds to their aromatic counterparts. Investigation of the reaction scope revealed that formaldehyde, as well as various aliphatic, aromatic and heteroaromatic aldehydes, works well as the aldehyde component. In addition, substituted anilines and diverse aminoheterocycles can be utilized in this process as the amine-containing component. Preliminary biological evaluation of the synthesized library identified a pyrimidine-based polycycle, which rivals the anticancer drug etoposide in its toxicity and apoptosis inducing properties toward a human T-cell leukemia cell line.

Graphical abstract: Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties

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Publication details

The article was received on 10 Sep 2007, accepted on 28 Sep 2007 and first published on 24 Oct 2007


Article type: Paper
DOI: 10.1039/B713820B
Citation: Org. Biomol. Chem., 2007,5, 3865-3872
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    Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties

    M. Manpadi, P. Y. Uglinskii, S. K. Rastogi, K. M. Cotter, Y. C. Wong, L. A. Anderson, A. J. Ortega, S. Van slambrouck, W. F. A. Steelant, S. Rogelj, P. Tongwa, M. Yu. Antipin, I. V. Magedov and A. Kornienko, Org. Biomol. Chem., 2007, 5, 3865
    DOI: 10.1039/B713820B

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