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

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

Volume: 3 Issue: 4

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

Affiliation:

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

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.

Cite this article as:

Bahsas Ali, Amaro-Luis Juan, Vazquez Yelkaira, Gupta Mahabir, Sortino Maximiliano, Zacchino A. Susana, Kouznetsov V. Vladimir, Puentes O. Cristian and Bohorquez R.R. Arnold, A Straightforward Synthetic Approach to Antitumoral Pyridinyl Substituted 7H-Indeno[2,1-c]Quinoline Derivatives Via Three-Component Imino Diels- Alder Reaction, Letters in Organic Chemistry 2006; 3 (4) . https://dx.doi.org/10.2174/157017806776114595