A Straightforward Synthetic Approach to Antitumoral Pyridinyl Substituted 7H-Indeno[2,1-c]Quinoline Derivatives Via Three-Component Imino Diels- Alder Reaction

Author(s): Ali Bahsas, Juan Amaro-Luis, Yelkaira Vazquez, Mahabir Gupta, Maximiliano Sortino, Susana A. Zacchino, Vladimir V. Kouznetsov, Cristian O. Puentes, Arnold R.R. Bohorquez.

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 4 , 2006

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Abstract:

A simple and efficient synthetic method of obtaining pyridinyl substituted indeno[2,1-c]quinoline derivatives has been developed. This method involves a three-component imino Diels-Alder cycloaddition between anilines, pyridinecarboxyaldehydes and indene as the key ring forming step and subsequent treatment of obtained 5,6,6a,11b-tetrahydroindeno[2,1-c]quinolines with powdered sulfur to give corresponding indeno[2,1-c]quinolines. Some of them were treated with potassium permanganate in acetone to afford the 7Hindeno[ 2,1-c]quinolin-7-ones. Most compounds of the series were devoid of antifungal properties against a panel of standard dermatophytes, however, nearly all of them were active against breast (MCF-7), lung (H-460) and central nervous system (SF-268) human cancer cell lines.

Keywords: Multi-component reaction, imino Diels-Alder reaction, indeno[2,1-c]quinolines, antitumoral and antifungal activities

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Article Details

VOLUME: 3
ISSUE: 4
Year: 2006
Page: [300 - 304]
Pages: 5
DOI: 10.2174/157017806776114595
Price: $65

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