229177-89-3Relevant academic research and scientific papers
Benzo[f]azino[2,1-a]phthalazinium Cations: Novel DNA Intercalating Chromophores with Antiproliferative Activity
Martínez, Valentín,Burgos, Carolina,Alvarez-Builla, Julio,Fernández, Gerónimo,Domingo, Alberto,García-Nieto, Raquel,Gago, Federico,Manzanares, Ignacio,Cuevas, Carmen,Vaquero, Juan J.
, p. 1136 - 1148 (2007/10/03)
New azaquinolizinium-type cations have been obtained from isochromane. The synthesis was completed over seven steps and included as the key feature an intramolecular Westphal condensation. This first example of the intramolecular process allowed the preparation of benzo[f]pyrido[2,1-a]phthalazinium and benzo[f]quino[2,1-a]phthalazinium salts, which were evaluated as DNA intercalators, DNA topoisomerase I inhibitors, and antiproliferative compounds. Both cationic systems behave as DNA intercalators and exhibit antiproliferative activity. The pentacyclic benzo[f]quino[2,1-a]phthalazinium cations also have an inhibitory effect on the catalytic activity of DNA topoisomerase I, without trapping of cleavage complexes. Structural characterization using density functional theory indicates that the fused ring systems are slightly nonplanar, and additional molecular modeling studies suggest a preferred orientation for the intercalating chromophores within a typical CpG or TpG intercalation site.
The first example of an intramolecular Westphal reaction. Synthesis of a new aza-quinolizinium type system
Martinez-Barrasa, Valentin,Burgos, Carolina,Izquierdo, M. Luisa,Alvarez-Builla, Julio,Vaquero, Juan J.
, p. 4115 - 4118 (2007/10/03)
The first example of an intramolecular Westphal condensation is described. To test the utility of this reaction, new benz(f)azino[2,1- a]phthalazinium salts have been prepared from appropriate dicarbonyl precursors.
