Synthesis and physicochemical characterization of novel 6-aminopyrido[3,4-c][1,9]phenanthrolines as aza-analogs of benzo[c]phenanthridines |
| |
Authors: | Christopher Meier Joscha Kotthaus Lars Stenzel Ulrich Girreser Dieter Heber Bernd Clement |
| |
Institution: | Pharmaceutical Institute, Department of Pharmaceutical and Medicinal Chemistry, Christian-Albrechts-University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany |
| |
Abstract: | Based on the 6-aminobenzoc]phenanthridines, a compound class showing noteworthy antitumor activity, an efficient one-step synthesis consisting of a base-catalyzed condensation of 2 equiv of 4-methylpyridine-3-carbonitrile and various aldehydes causing twofold ring closure is described. The obtained 6-amino-11,12-dihydropyrido3,4-c]1,9]phenanthrolines could be aromatized with Pd/C at high temperatures to form 6-aminopyrido3,4-c]1,9]phenanthrolines. All compounds were systematically characterized regarding both lipophilicity and solubility and a high cytotoxic potential was evaluated in preliminary in vitro studies. Compared to formerly described 6-aminobenzoc]phenanthridines our newly developed phenanthrolines turned out to possess improved drugability, due to significantly increased water-solubility and decreased lipophilicity. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|