三有机锡(4R)-3-[[(2S)-5-氧-2-吡咯烷基]羰基]-4-噻唑烷甲酸酯的合成、结构和体外抗癌活性

Synthesis, Structure and in vitro Anti-tumor Activity of Triorganotin(4R)-3-[[(2S)-5-Oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylates

利用三有机锡氢氧化物和手性配体(4R)-3-[[(2S)-5-氧-2-吡咯烷基]羰基]-4-噻唑烷甲酸(HL)反应合成了3个三有机锡(4R)-3-[[(2S)-5-氧-2-吡咯烷基]羰基]-4-噻唑烷甲酸酯R3SnL[1,R=c-C6H11(a),C6H5(b),C6H5C(CH3)2CH2(c)],通过元素分析、IR、1H NMR和X-射线单晶衍射表征了其结构。化合物1a属正交晶系,P212121空间群;化合物1b属单斜晶系,P21空间群。二者均为由羧基氧和内酰胺羰基氧桥联配位形成的右螺旋链状有机锡配位聚合物,锡原子具有五配位[SnC3O2]畸变三角双锥构型。化合物1a和1b对体外2种人癌细胞Colo205和Bcap37增殖均有强的抑制作用,其活性为1b>1a。

Three triorganotin（4R）-3-[[（2S）-5-oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylates, R3SnL（1, R=c-C6H11, a; C6H5, b; C6H5C（CH3）2CH2, c）, have been synthesized by the reaction of triorganotin hydroxide with（4R）-3-[[（2S）-5-oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic acid（HL） and characterized by means of elemental analysis, IR,1H NMR spectra and X-ray single crystal diffraction. The crystal of 1a belongs to orthorhombic space group P212121, and the crystal of 1b belongs to monoclinic space group P21. Compounds 1a and 1b both possess a trans-C3SnO2 trigonal bipyramidal geometry with the axial positions occupied by the carboxylate oxygen and the lactam oxygen of pyroglutamyl of an adjacent molecule and form a one-dimensional right-handed helix. The compounds 1a and 1b have potent in vitro anti-tumor activity against two human tumor cell lines, Colo205 and Bcap37. The activity order is 1b1a. CCDC： 837609, HL; 837610, 1a; 837611, 1b.