CN101434616B - 一种有机锡schiff碱配位化合物及其制备方法与应用 - Google Patents
一种有机锡schiff碱配位化合物及其制备方法与应用 Download PDFInfo
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- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 abstract description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052697 platinum Inorganic materials 0.000 abstract description 3
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- 239000003513 alkali Substances 0.000 abstract 4
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- 229910052799 carbon Inorganic materials 0.000 description 2
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Abstract
本发明公开了一种有机锡schiff碱配位化合物,结构式为:
Description
技术领域
本发明涉及一种有机锡schiff碱配位化合物,及其制备方法,以及该化合物在制备抗癌药物中的应用。
背景技术
金属有机化合物(Organometallic compound)是指含有一个或多个金属-碳键(M-C键)的化合物。有机锡化合物因其在合成、催化、防污、药物、PVC稳定剂等方面的广泛应用而受到人们的广泛关注。上世纪80年代,在对金属抗癌药物的研究和筛选的过程中,Crowe A.J.等发现某些有机锡化合物具有比顺铂更高的抗肿瘤活性,从而揭开了有机锡化学发展的新篇章。许多传统的表征手段如红外光谱、核磁共振谱、质谱等在有机锡化合物中的成功运用,为其研究提供了重要的保障;而X-射线衍射技术的开发和应用更为其提供了直观而准确的结构信息。
Schiff碱化合物具有一定的药理学和生理学的活性,又因本身含有多重配位可能性,且配位基间的空间位阻不大而易于双核配合物的形成,近几年一直是人们的研究对象。腙类配体是众多schiff碱中的一种,它是以氮原子和氧原子为配位原子,与生物环境较为接近,人们对酰腙及其过渡金属配合物的结构和性质已有大量的报道,研究结果表明,酰腙类配体在形成配合物后的生物活性比配位前明显加强,其配合物有广泛的生物和药物活性。
发明内容
针对上述现有技术,本发明提供了一种新的有机锡schiff碱配位化合物,并提供了该化合物的制备方法及其应用。
一种有机锡schiff碱配位化合物,结构式如下:
其中,nBu表示正丁基。
一种有机锡schiff碱配位化合物的制备方法:向圆底烧瓶中加入2.5~3.0mmol的2-羟基萘醛对苯双酰腙、10~15mmol的乙醇钠及50~100mL的甲醇,搅拌0.5~2h,随后加入2.5~5.0mmol的二丁基二氯化锡,在搅拌下,加热回流5~8h;冷却,过滤,滤液用旋转蒸发仪蒸干,得黄色固体,然后用二氯甲烷-乙醇重结晶,其中,二氯甲烷与乙醇的体积比为1:1~1:2,得橙黄色晶体,即为有机锡schiff碱配位化合物,产率70~82%。
所述的一种有机锡schiff碱配位化合物在制备治疗胃癌、鼻咽癌、人肝癌或白血病的药物中应用。
本发明的有机锡schiff碱配位化合物分子式为C46H54N4O4Sn2,分子量为964.37,具有较高的抗癌活性,可以其为原料制备治疗胃癌、鼻咽癌、人肝癌或白血病的药物。与目前普遍使用的铂类抗癌相比,本发明的有机锡配位化合物具有抗癌活性较高、脂溶性好、成本低、制备方法简单等特点,为开发抗癌药物提供了新途径。
具体实施方式
下面结合实施例对本发明作进一步的说明:
实施例1:制备有机锡schiff碱配位化合物:向250mL的圆底烧瓶中加入1.26g(2.5mmol)2-羟基萘醛对苯双酰腙、10mmol的乙醇钠以及50mL甲醇,搅拌0.5h,随后加入1.52g(2.5mmol)二丁基二氯化锡,在搅拌下,加热回流5h。冷却,过滤,滤液用旋转蒸发仪蒸干,得黄色固体,然后用二氯甲烷-乙醇(V:V=1:1)重结晶,得橙黄色晶体1.69g,即为有机锡schiff碱配位化合物,产率70%。
经红外光谱分析和核磁共振分析,结果如下:
红外光谱(KBr,cm-1):IR(KBr,cm-1):1606(s,C=N),1585(m,C=N-N=C),564(m,Sn-O),470(w,Sn-N)。
1H NMR(400MHz,CDCl3,25℃):9.73(s,2H,CH),8.18(s,4H,ArH),8.10(d,2H,J=8.4Hz,Np),7.77(d,2H,J=9.2Hz,Np),7.70(d,2H,J=8.0Hz,Np),7.54(t,2H,J=7.6Hz,Np),7.32(t,2H,J=7.6Hz,Np),6.96(d,2H,J=9.2Hz,Np),1.51-1.71(m,16H,-CH2CH2-Me),1.36-1.45(m,8H,Sn-CH2-),0.87(t,J=6.8Hz,12H,-CH3).13C NMR(100MHz,CDCl3,25℃):169.46,168.01,157.12,136.68,135.67,133.81,129.16,128.04,127.36,127.14,124.37,123.01,119.16,107.08,26.86,26.46,22.07,13.60.119Sn NMR(149MHz,CDCl3,25℃):-188.78.
元素分析:计算值C46H54N4O4Sn2:C,57.29;H,5.64;N,5.81;实测值:C,57.18;H,5.59。
实施例2:制备有机锡schiff碱配位化合物:向250mL的圆底烧瓶中加入1.26g(2.5mmol)2-羟基萘醛对苯双酰腙、10mmol乙醇钠以及100mL甲醇,搅拌1h,随后加入2.13g(3.5mmol)二丁基二氯化锡,在搅拌下,加热回流6h。冷却,过滤,滤液用旋转蒸发仪蒸干,得黄色固体,然后用二氯甲烷-乙醇(V:V=1:1.5)重结晶,得橙黄色晶体,即为有机锡schiff碱配位化合物,产率82%。
实施例3:制备有机锡schiff碱配位化合物:向250mL的圆底烧瓶中加入1.512g(3.0mmol)2-羟基萘醛对苯双酰腙、15mmol乙醇钠以及100mL甲醇,搅拌2.0h,随后加入3.04g(5.0mmol)二丁基二氯化锡,在搅拌下,加热回流8h。冷却,过滤,滤液用旋转蒸发仪蒸干,得黄色固体,用二氯甲烷-乙醇(V:V=1:2)重结晶,得橙黄色晶体,即为有机锡schiff碱配位化合物,产率76%。
实施例4:制备有机锡schiff碱配位化合物:向250mL的圆底烧瓶中加入2.8mmol 2-羟基萘醛对苯双酰腙、13mmol乙醇钠以及750mL甲醇,搅拌1.5h,随后加入4.0mmol二丁基二氯化锡,在搅拌下,加热回流7h。冷却,过滤,滤液用旋转蒸发仪蒸干,得黄色固体,用二氯甲烷-乙醇(V:V=1:2)重结晶,得橙黄色晶体,即为有机锡schiff碱配位化合物,产率74%。
试验例:本发明的有机锡schiff碱配位化合物,其体外抗癌活性测定是通过MTT与SRB两种实验方法实现的,其原理为:
MTT分析法:以代谢还原3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl terrazolium bromide为基础,活细胞线粒体中存在与NADP相关的脱氢酶,可将黄色MTT还原成不溶性蓝紫色的Formazan,死细胞无此酶,MTT不被还原,用DMSO溶解Formazan后,可用酶标仪测定特征波长的光密度,进行有关数据处理,得出结论。
SRB分析法:Sulforhodamine B是一种粉红色蛋白质结合染料,可溶于水,可与生物大分子中的碱性氨基酸结合,其在515nm的OD读数与细胞数呈良好的线性关系,可定量计算出药物加量与有关细胞数目的数据。
以SRB分析法对人肝癌Bel-7402细胞株、人胃癌BGC-823细胞株、人鼻咽癌KB细胞株进行分析,以MTT分析法对人白血病HL-60细胞株进行分析,测定其IC50值,结果见表1,结论为:由表中数据可知,本发明的抗癌药物,对人肝癌的抗癌活性较高,对于人胃癌、白血病的体外活性均大于顺铂,可作为抗癌药物的候选化合物。
表1有机锡schiff碱配位化合物抗癌药物体外活性测试数据
人肝癌 | 人胃癌 | 人鼻咽癌 | 人白血病 | |
样品编号 | 08-28 | 08-28 | 08-28 | 08-28 |
样品IC50(μM) | 1.133 | 4.132 | 4.778 | 5.144 |
顺铂IC50(μM) | 7.680 | 6.700 | 3.180 | 6.100 |
方法 | SRB | SRB | SRB | MTT |
细胞株 | Bel-7402 | BGC-823 | KB | HL-60 |
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CN102127106B (zh) * | 2010-12-30 | 2013-05-22 | 聊城大学 | 一种二苯基二氯化锡配合物及其制备方法与应用 |
CN102399168B (zh) * | 2011-09-20 | 2014-07-23 | 聊城大学 | 一种Schiff碱Cu(II)配位化合物及其制备方法与应用 |
CN102718794A (zh) * | 2012-07-09 | 2012-10-10 | 聊城大学 | 一种双酰腙类Schiff碱二苯基锡(Ⅳ)配合物及其制备方法与应用 |
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