Structures of platinum(II) complexes of 2-aminomethylaziridine and S-2-aminomethylazetidine and correlation of anticancer activities of (2-aminomethylazacycloalkane)platinum(II) complexes with the geometry of the chelate rings formed with platinum(II).
The spectroscopic properties of platinum(II) complexes with 2-aminomethyl-derivatives of small-membered 1-aza-cycloalkane, i.e., =2-aminomethylaziridine=azida and S-2-aminomethylazetidine=S-azeda, and the crystal structures of their dichloro complexes demonstrate that the conformation of the fused three- (azida) or four- (S-azeda) and five-membered chelate ring formed by the coordination of S-azida and S-azeda to platinum(II) has an S(N) absolute configuration at the secondary amine site and that the two alkyl groups extend axially from the five-membered chelate ring. The chelate ring of the azida is more planar than the S-azeda or other 2-aminomethyl-1-azacycloalkanes. The anticancer activity reported for azeda and 2-aminomethylpyrrolidine appears to be related to their coordination structure, namely the presence of cis-fused successive rings.
Goto
Masafumi
M
Graduate School of Pharmaceutical Sciences, Kumamoto University, Oe-Honmachi, Kumamoto 862-0973, Japan. gmphiwin@gpo.kumamoto-u.ac.jp
Tsutsui
Hisashi
H
Matsuda
Syuuichi
S
Tanaka
Yoshitomo
Y
Tsuruda
Nobuhiro
N
Kurosaki
Hiromasa
H
D000970:Antineoplastic Agents / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009944:Organoplatinum Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship
C488441:2-aminomethylaziridine; D000970:Antineoplastic Agents; D001384:Azetidines; D001388:Aziridines; D002614:Chelating Agents; D007202:Indicators and Reagents; D009944:Organoplatinum Compounds; C488442:S-2-aminomethylazetidine