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

2006; Bentham Science Publishers; Volume: 3; Issue: 4 Linguagem: Inglês

10.2174/157017806776114595

1875-6255

Alı́ Bahsas, Juan M. Amaro‐Luis, Yelkaira Vázquez, Mahabir P. Gupta, Maximiliano Sortino, Susana Zacchino, Vladímir V. Kouznetsov, Cristian Ochoa Puentes, Arnold R. Romero Bohórquez,

Cancer therapeutics and mechanisms

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