Structures of Platinum(II) Complexes of 2-Aminomethylaziridine and <i>S</i>-2-Aminomethylazetidine and Correlation of Anticancer Activities of (2-Aminomethylazacycloalkane)platinum(II) Complexes with the Geometry of the Chelate Rings Formed with Platinum(II)

Abstract

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-(Sazeda) 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.

Simple Trans-Platinum Complex Bearing 3-Aminoflavone Ligand Could Be a Useful Drug: Structure-Activity Relationship of Platinum Complex in Comparison with Cisplatin

“…In this group, there are 18 crystal structures recorded in the CSD as compounds with the confirmed biological activity of cytotoxic, antitumor, or anticancer properties. It is important to stress that the majority of the compounds displaying such biological activity represent a class of chelatecomplexes of cis-configuration: BERDAE, BERDEI [26], CCENPT01 [27], DIVXOV [28], FITFUJ [29], LAYZEQ [30], LEFFAD [31], LIXTOB [32], PEXTIV [33], PIFGIU [34], SUDMIN02 [35], TAJTED [36], TUPQIE [37], UCIZUC [38], and YIDVUD [39]. In contrast, the title trans-Pt(3-af) 2 Cl 2 , recorded with MONVIW reference code, together with RIWCEG [40] and VOHBAW [41] structures, belong to a group of only a few trans platinum complexes showing cytotoxic activity.…”