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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

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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.

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Keywords: Multi-component reaction; antitumoral and antifungal activities; imino Diels-Alder reaction; indeno2,1-cquinolines

Document Type: Research Article

Affiliations: Laboratorio de Quimica Organica y Biomolecular, Escuela de Quimica, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia.

Publication date: 2006-04-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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