Synthesis and cytotoxic activity of benzopyran-based platinum(II) complexes.
A series of benzopyran-based platinum complexes of types 4 and 5 were synthesized as potential anticancer agents. The novel compounds were synthesized in several steps using simple and efficient chemistry. The newly synthesized compounds were evaluated for their biological efficacy and showed significant in vitro cytotoxic activity in different hormone-dependent and -independent breast cancer cell lines. Docking and other molecular modeling experiments were also performed for one of the potent compounds, 5f, which showed that both the possible enantiomeric forms (5f with 3R,4R and 5f with 3S,4S) of the molecule have comparable lowest energy (for 5f with 3R,4R, -31.953 kcal/mol and for 5f with 3S,4S, -31.944 kcal/mol). The 3D QSAR was examined for the derivatives of both enantiomeric forms and a novel relationship for the 3S,4S derivatives is discussed.
Département de Chimie-Biologie, Groupe de Recherche en Biopathologies Cellulaires et Moléculaires, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Que., Canada G9A 5H7.
Atul
A
Gupta
Sanat K
SK
Mandal
Valérie
V
Leblanc
Caroline
C
Descôteaux
Eric
E
Asselin
Gervais
G
Bérubé
D000970:Antineoplastic Agents / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D001943:Breast Neoplasms / Q000188:drug therapy*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009944:Organoplatinum Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship; D011960:Receptors, Estrogen / Q000378:metabolism; D020845:Selective Estrogen Receptor Modulators / Q000378:metabolism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001578:Benzopyrans; D009944:Organoplatinum Compounds; D011960:Receptors, Estrogen; D020845:Selective Estrogen Receptor Modulators