Synthesis, cytotoxic evaluation, and DNA binding of novel thiazolo[5,4- b]quinoline derivatives

• Published in: Bioorganic & medicinal chemistry Vol. 16; no. 3; pp. 1142 - 1149
• Main Authors: Loza-Mejía, Marco A., Maldonado-Hernández, Karina, Rodríguez-Hernández, Fernando, Rodríguez-Sotres, Rogelio, González-Sánchez, Ignacio, Quintero, Angelina, Solano, José D., Lira-Rocha, Alfonso
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.02.2008; Elsevier Science
• Subjects: Antineoplastic agents; Antitumoral; Biological and medical sciences; Cell Line, Tumor; Cell Survival - drug effects; Cytotoxic activity; DNA - genetics; DNA binding; General aspects; Humans; Magnetic Resonance Spectroscopy; Medical sciences; Molecular Structure; Pharmacology. Drug treatments; Quinolines - chemical synthesis; Quinolines - chemistry; Quinolines - toxicity; Structure-Activity Relationship; Thiazoles - chemistry; Thiazolo[5,4- b]quinoline derivatives; Antitumoral; Thiazolo[5,4- b]quinoline derivatives; Structure–activity relationship; DNA binding; Cytotoxic activity; Antineoplastic agent; Human; Thiazolo[5,4-b]quinoline derivatives; Cytotoxicity; Uterine cervix; In vitro; Hela cell line; Biological fixation; Cell line; Structure activity relation; DNA; Structure-activity relationship; Colon; Chemical synthesis; Tumor cell
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2007.10.084

Electron-withdrawing/electron-releasing substituents attached at 3′ and 4′-position of anilino ring or alkylamino residues were relevant to the cytotoxicity and DNA intercalation of several novel thiazolo[5,4- b]quinoline derivatives. A series of novel alkylamino and 9-anilinothiazolo[5,4- b]quinolines were synthesized as potential antitumoral agents. The in vitro cytotoxicity of these compounds was evaluated on several cell lines. The inclusion of electron-withdrawn/acceptor hydrogen-bond groups at position 3′ of the anilino ring and the presence of an alkylamino chain on the tricyclic framework (regardless of its position) seem to be structural features relevant to cytotoxic activity.