三烃基锡肉桂酸酯的合成、结构、抗癌活性及热稳定性

引用本文: 冯泳兰, 庾江喜, 邝代治, 谭宇星, 张复兴, 蒋伍玖, 朱小明, 郑建华. 三烃基锡肉桂酸酯的合成、结构、抗癌活性及热稳定性[J]. 无机化学学报, 2015, (5): 908-914. doi: 10.11862/CJIC.2015.109 shu

Citation: FENG Yong-Lan, YU Jiang-Xi, KUANG Dai-Zhi, TAN Yu-Xing, ZHANG Fu-Xing, JIANG Wu-Jiu, ZHU Xiao-Ming, ZHENG Jian-Hua. Syntheses, Crystal Structures, Anti-tumor Activity and Thermal Stability of Tri-alkyltin Cinnamic Carboxylates[J]. Chinese Journal of Inorganic Chemistry, 2015, (5): 908-914. doi: 10.11862/CJIC.2015.109 shu

三烃基锡肉桂酸酯的合成、结构、抗癌活性及热稳定性

冯泳兰 ^1, ,
庾江喜 ^1, ,
邝代治 ^{1,
,} ,
谭宇星 ^1,2, ,
张复兴 ^1, ,
蒋伍玖 ^1, ,
朱小明 ^1, ,
郑建华 ^1,

1.
1 功能金属有机材料湖南省普通高等学校重点实验室, 衡阳师范学院化学与材料科学系, 衡阳 421008;
2.
2 湖南师范大学化学化工学院, 长沙 410081

通讯作者: 邝代治 hnkcq@qq.com

基金项目:
湖南省自然科学基金(No.13JJ3112) (No.13JJ3112)

湖南省科技计划(No.2014NK3086) (No.2014NK3086)

湖南省高校创新平台开放基金(No.13K105,14K014) (No.13K105,14K014)

重点实验室开放基金(No.13K01,GN14K01) (No.13K01,GN14K01)

湖南省十二五重点建设学科(材料物理与化学) (材料物理与化学)

衡阳师范学院协同创新中心培育项目(No.12XT02) (No.12XT02)

青年骨干教师培养计划(2012) (2012)

湖南省大学生研究性学习项目(CX1301)资助。 (CX1301)

摘要: 肉桂酸分别与μ-氧-双(三丁基锡)、三环己基氢氧化锡反应,合成了2个三烃基锡羧酸酯[n-Bu₃Sn(O₂CC₈H₇)]_n(1)和Cy₃Sn(O₂CC₈H₇)·MeOH(2)。经IR、¹ H和¹³C NMR、元素分析和X-射线单晶衍射表征结构。配合物1属单斜晶系,空间群P2₁/c,晶体学参数:a=1.05381(2)nm,b=1.85066(4)nm,c=2.49500(5)nm,β=106.3460(10)°,V=4.66918(16)nm³,Z=4,D_c=1.244g·cm^-3,μ(MoKα)=1.103mm^-1,F(000)=1808,R₁=0.0519,wR₂=0.1320。配合物2,三斜晶系,空间群P1,晶体学参数:a=1.3388(3)nm,b=1.4926(4)nm,c=1.7884(5)nm,α=67.066(14)°,β=69.631(15)°,γ=63.938(14)°,V=2.8882(13)nm³,Z=4,D_c=1.259g·cm^-3,μ(MoKα)=0.908mm^-1,F(000)=1144,R₁=0.0506,wR₂=0.1102。2个配合物中心锡原子均为五配位畸变三角双锥构型,1通过羧基氧原子桥联成一维无限链状;2的晶体中存在着O-H…O氢键和π-π堆积作用,扩展成二维网状结构。初步测试表明:1对人癌细胞Colo205、HepG2、MCF-7、Hela、NCI-H460增殖均有较强的抑制作用,且对上述人癌细胞的抑制活性均高于卡铂,比2可能更具药用价值;1和2分别可以在145、190℃以下稳定。

关键词:

三烃基锡;肉桂酸;晶体结构;抗癌活性

English

Syntheses, Crystal Structures, Anti-tumor Activity and Thermal Stability of Tri-alkyltin Cinnamic Carboxylates

1.
1 Key Laboratory of Functional Organometallic Materials of College of Hunan Province, Department of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China;
2.
2 College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China

Corresponding author: 邝代治 hnkcq@qq.com

Received Date: 12 November 2014
Fund Project:
湖南省自然科学基金(No.13JJ3112)

湖南省科技计划(No.2014NK3086)

湖南省高校创新平台开放基金(No.13K105,14K014)

重点实验室开放基金(No.13K01,GN14K01)

湖南省十二五重点建设学科(材料物理与化学)

衡阳师范学院协同创新中心培育项目(No.12XT02)

青年骨干教师培养计划(2012)

湖南省大学生研究性学习项目(CX1301)资助。

Abstract: Two trialkyltin carboxylates [n-Bu₃Sn(O₂CC₈H₇)]_n (1) and Cy₃Sn(O₂CC₈H₇)·MeOH (2) were synthesized by the reactions of cinnamic acid with bis(tributyltin) oxide and tricyclohexyltin hydroxide, respectively. Their structures were characterized by IR, ¹H and ¹³C NMR, elemental analysis and X-ray crystal diffraction. The crystal of complex 1 belongs to monoclinic system, space group P2₁/c, a=1.05381(2) nm, b=1.85066(4) nm, c=2.49500(5) nm, β=106.3460(10)°, V=4.66918(16) nm³, Z=4, D_c=1.244 g·cm^-3, μ(Mo Kα)=1.103 mm^-1, F(000)= 1808, R₁=0.0519, wR₂=0.1320. The crystal of complex 2 belongs to triclinic system, space group P1, a=1.3388(3) nm, b=1.4926(4) nm, c=1.7884(5) nm, α=67.066(14)°, β=69.631(15)°, γ=63.938(14)°, V=2.8882(13) nm³, Z=4, D_c=1.259 g·cm^-3, μ(Mo Kα)=0.908 mm^-1, F(000)=1144, R₁=0.0506, wR₂=0.1102. The central tin atoms of two complexes are aberrant trigonal bipyramidal configurations with five coordination, and a 1Dinfinite chain of 1 is bridged by carboxyl Oatoms, while a 2D network of 2 is generated by O-H…O hydrogen bonds and π-π effects. Moreover, the preliminary tests showed that complex 1 displayed stronger than carboplatin in vitro anti-tumor activity against five human tumor cell lines, Colo205, HepG2, MCF-7, Hela and NCI-H460, and had higher medicinal value than complex 2. Thermogravimetric analysis shows the complexes were stable up to 145 or 190 ℃, respectively.

Key words:

trialkyltin;cinnamic acid;crystal structure;anti-tumor activity

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

三烃基锡肉桂酸酯的合成、结构、抗癌活性及热稳定性

通讯作者: 邝代治 hnkcq@qq.com

English

Syntheses, Crystal Structures, Anti-tumor Activity and Thermal Stability of Tri-alkyltin Cinnamic Carboxylates

Corresponding author: 邝代治 hnkcq@qq.com

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

三烃基锡肉桂酸酯的合成、结构、抗癌活性及热稳定性

通讯作者: 邝代治 hnkcq@qq.com

English

Syntheses, Crystal Structures, Anti-tumor Activity and Thermal Stability of Tri-alkyltin Cinnamic Carboxylates

Corresponding author: 邝代治 hnkcq@qq.com

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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