Amino- and polyaminophthalazin-1(2 H )-ones: synthesis, coordination properties, and biological activity

• Published in: Beilstein journal of organic chemistry Vol. 17; no. 1; pp. 558 - 568
• Main Authors: Malinowski, Zbigniew, Fornal, Emilia, Sumara, Agata, Kontek, Renata, Bukowski, Karol, Pasternak, Beata, Sroczyński, Dariusz, Kusz, Joachim, Małecka, Magdalena, Nowak, Monika
• Format: Journal Article
• Language: English
• Published: Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 25.02.2021; Beilstein-Institut
• Subjects: amination; Biological activity; Cancer; Cell lines; Chemistry; complexes; Copper; Cytotoxicity; Full Research Paper; Ligands; Metal ions; Nitrogen; Palladium; pd cross-coupling; phthalazinone; Polyamines; Solvents; Pd cross-coupling; phthalazinone; amination; cytotoxicity; complexes
• ISSN: 1860-5397; 2195-951X; 1860-5397
• DOI: 10.3762/bjoc.17.50

Amino- and polyaminophthalazinones were synthesized by the palladium-catalyzed amination (alkyl- and arylamines, polyamines) of 4-bromophthalazinones in good yields. The coordinating properties of selected aminophthalazinones towards Cu(II) ions were investigated and the participation of the nitrogen atoms in the complexation of the metal ion was shown. A biological screening of the potential cytotoxicity of selected synthesized compounds on HT-29 and PC-3 cell lines, as well as on the L-929 cell line, proved that some amino derivatives of phthalazinone show interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays are reported.