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.pdf

第30卷第9期
无机化学学报
Vol 30 No 9
2014年9月
CHINESE JOURNAL OF INORGANIC CHEMISTRY
2087~2092
三有机锡(4R)-3-[(2S)-5-氧2-吡咯烷基碁]羰基』4-噻唑烷甲酸酯
的合成、结构和体外抗癌活性
田来进*王晓龙1郑晓亮2董云赛1刘志坤1
曲阜师范大学医药中间体与天然药物山东省高校重点实验室,曲阜27316
(浙江省医学科学院药物研究所,杭州310013)
摘要: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(H反应合成了3个三有机锡(4R)-
3-[(2S)-5-氧-2-吡咯烷基碁]羰基]-噻唑烷甲酸酯RSnL[I,R=c-CHn(),CH(b),CHC(CH2CH1(e)],通过元素分析、IR、HNMR
和X-射线单晶行射表征了其结构。化合物1a属正交晶系,P21212,空间群;化合物1b属单斜晶系,P2空间群。二者均为由幾基
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[SnC:O]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。
关键词:有机锡羧酸酯;匹多莫德;(R)-4-噻唑烷甲酸;晶体结构;抗癌活性
中图分类号:0614.432
文献标识码:A文章编号:1001-48612014)09-2087-06
DOI:10.11862/CJIC.2014.301
Synthesis, Structure and in vitro Anti-tumor Activity of Triorganotin
(4R)-3-[2S)-5-0x0-2-pyrrolidinyllcarbonyll-4-thiazolidinecarboxylates
TIAN Lai-jin WANG Xiao-long ZHENG Xiao-liang DONG Yun-sai LIU Zhi-kun
Key Laboratory of Phamaceutical Intermediates and Natura Medicine, ufu Normal Univesity, uf, Shandong 273165, Chi
Institute of Materia Medica Zhejiang Academy of Medical Sciences, Hangzhou 310013, China)
Abstract: Three triorganotin(4R)3-(S)-5-0x0-2-yrrolidinlcarbon l-4-thiazolidinecarboxylates, R Snl(, R
C-CH, a; Cshs, b; COHSC(CH)2CH, c), have been synthesized by the reaction of triorganotin hydroxide with
(4)-3-2)5-x0-2-yrroliilcaony-4hiazliinecaxyli acid H)an chaize by means of
elemental analysis, IR, H NMR spectra and X-ray single crystal diffraction. The crystal of la belongs to
orthorhombic space group P2 212, and the crystal of Ib belongs to monoclinic space roup P2,. Compounds 1a
and Ib both possess a trans-c n02 trigonal bipyramidal geometry with the axial positions occupied by th
carboxy late oxygen and the lactam oxygen of pyroglutamyl of an adjacent molecule and form a one-dimensional
right-handed helix. The compounds la and 1b have potent in witro anti-tumor activity against two human tumor
cell lines, Colo205 and Bcap37. The activity order is Ib>la. CCDC: 837609, HL; 837610, Ia; 837611, 1b
Key words: organotin carbox late; pidotimod; (4R 4 hiazli x li acid; crystal structure; anti-tumor activity
收稿日期:2014-04-12。收修改稿日期:2014-05-16
山东省自然科学基金(No.ZR2013BMO0の)和国家自然科学基金(No,21302110资助课题。
*通讯联系人。E-mail.laijintian]63.com