Synthesis of Novel Conformationally Constrained Pyrazolo[4,3-c]quinoline Derivatives as Potential Ligands for the Estrogen Receptor

Konstantinos M. Kasiotis; Nikolas Fokialakis; Serkos A. Haroutounian

doi:10.1055/s-2006-926466

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Synthesis of Novel Conformationally Constrained Pyrazolo[4,3-c]quinoline Derivatives as Potential Ligands for the Estrogen Receptor

Konstantinos M. Kasiotis^a, Nikolas Fokialakis^b, Serkos A. Haroutounian*^a
^a Chemistry Laboratory, Agricultural University of Athens, Iera odos 75, Athens 11855, Greece
Fax: +30(210)5294265; e-Mail: sehar@aua.gr;
^b Division of Pharmacology and Chemistry of Natural Products, Faculty of Pharmacy, University of Athens, Panepistimiopolis, Zografou 15771, Athens, Greece

Abstract

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Abstract

The preparation of three novel classes of pyrazolo[4,3-c]quinoline derivatives is reported. The easily accessible 2,3-dihydro-1H-quinolin-4-ones were used as the starting materials and were functionalized with three different acylating agents affording their respective constrained core substrates. The latter by condensation with phenyl(or 4-methoxyphenyl)hydrazines and subsequent debenzylation or demethylation provided the desired pyrazole derivatives. Some interesting features emerged with respect to the regioselectivity and mechanism of these reactions.

Key words

quinolines - fused ring-systems - acylations - pyrazole - estrogens

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