CN111333676A - 一种具有抗肿瘤活性的烃基锡配合物及其制备方法 - Google Patents
一种具有抗肿瘤活性的烃基锡配合物及其制备方法 Download PDFInfo
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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Abstract
本申请提供了一种具有抗肿瘤活性的烃基锡配合物及其制备方法，并对其活性进行测试，其体现出比顺铂强很多的活性，尤其是对人结肠癌有很高的活性，是潜在的临床抗肿瘤药物的候选者。
Description
技术领域
本发明涉及一种具有抗肿瘤活性的炔基膦酸的烃基锡配合物，属于药物化学领域。
背景技术
烃基锡的膦(磷)酸衍生物具有较强的杀虫、杀菌及除草等生物活性，受到人们的极大关注。关于炔基膦酸的烃基锡配合物的研究已有文献报道，但这些文献多集中在合成和结构研究阶段，对药理活性的研究较少，且多是测试了其杀菌和杀螨虫等的活性，对该类配合物的抗肿瘤活性的研究较少。
而锡配合物通常也具有一定的抗肿瘤活性，基于此考虑，为了探索新的抗癌类类药物，我们在现有文献的基础上对已有的炔基膦酸的烃基锡配合物进行了适当的结构改进和筛选。通过生物活性初步试验表明，该类炔基膦酸的烃基锡配合物确实具有一定的抗癌活性，尤其是其中几种特定结构的配合物体现出优良的活性。
发明内容
在充分调研了现有技术的基础上，本申请筛选了新的具有抗癌活性的炔基膦酸的烃基锡配合物，从而提供新的抗肿瘤候选化合物。
为达到上述目的，本发明创造的技术方案是这样实现的：
一种具有抗肿瘤活性的炔基膦酸锡配合物，其特征在于，具有以下结构：
其中，R1选自正丁基、叔丁基、苯基、苄基、对氯苄基、二甲基苄基；
且R2为任选取代的烷基、芳基、杂芳基；
优选R2为任选取代的C1-C4烷基、C6-C10芳基、C6-C10杂芳基；
进一步优选R2为任选取代的苯基；
所述任选取代的取代基为卤素，如F、Cl、Br、I，C1-C8烷基，如甲基、乙基、丙基、叔丁基，C1-C8烷氧基，如甲氧基、乙氧基、丙氧基、叔丁氧基，硝基、氰基、三氟甲基；取代基的个数为1、2、3、4、5。
上述炔基膦酸锡配合物用于制备抗癌药物，具体为针对子宫颈癌、乳腺癌、肺腺癌、肝癌、前列腺癌、结肠癌等。
本发明的配合物具有如下有益效果：
本发明针对炔基膦酸锡配合物进行结构修饰，并从中筛选出具有抗癌活性的化合物，其体现出比顺铂强很多的活性，尤其是对人结肠癌有很高的活性，是潜在的临床抗肿瘤药物的候选者。实验过程中发现，烷基锡部分中的烷基部分(即R1)的改变对配合物的生物活性有较大影响，以正丁基的效果最好；苯环上取代基的种类也对其生物活性有较大贡献。
具体实施方式
为了使本发明的目的、技术方案和优点更加清楚，下面对本发明的代表性实施例进行详细的描述，而不局限于此。
实施例1三正丁基锡(IV)(4-甲氧基苯基)乙炔基膦酸衍生物的合成
产物的结构式为：
在100mL的圆底烧瓶中，加入3mmol三正丁基氯化锡和20mL无水甲醇，搅拌，三丁基氯化锡完全溶解后，加入3.2mmol(4-甲氧基苯基)乙炔基磷酸单钠，回流下搅拌反应4.5小时，冷却，过滤，滤液减压浓缩，加入适量石油醚并过滤，真空浓缩得产品，收率87％。
元素分析数据：Anal.Calcd.For C21H35O4PSn(％)：C 53.33,H 7.04,Sn 23.69；Found(％)：C 53.37,H 7.06,Sn 23.73。核磁氢谱数据：1H NMR/δ0.79-0.83(9H),1.24-2.03(18H),3.42-4.02(3H),7.33-7.90(4H)。
实施例2
按照实施例1的方法，选择苯基乙炔基磷酸单钠为原料，制备了三正丁基锡(IV)苯基乙炔基膦酸衍生物。
实施例3化合物的抗肿瘤活性测试
实施例1的化合物命名为化合物1，实施例2的化合物为化合物2。
MCF-7，HT-29，A549和HepG2细胞取自美国组织培养库，用含10％牛胎血清培养液，在含CO2的培养箱内于37℃下培养。用MTT法检测细胞增殖与生长抑制情况。调整实验细胞数量使在570nm获得吸光度，将化合物测试药液(0.1nmol/L～10μmol/L)设置6个浓度，处理细胞72h，每个浓度至少3个平行实验和3次重复实验，用统计分析确定IC50值。
以顺铂为对照，测试了化合物l～2对肿瘤细胞：MCF7(人乳腺癌细胞)、HT-29(人结肠癌细胞)、A549(人肺癌细胞)和HepG2(肝癌细胞)的体外生长抑制活性，结果见下表。发现化合物对所研究细胞显示出比顺铂更强的抗癌活性，尤其对HT-29的抑制作用更明显，可作为候选的抗癌化合物。
表1
Claims (6)
1.一种具有抗肿瘤活性的炔基膦酸锡配合物，其特征在于，具有以下结构：
其中，R1选自正丁基、叔丁基、苯基、苄基、对氯苄基、二甲基苄基；
2.根据权利要求1所述的炔基膦酸锡配合物，其特征在于：
R2为任选取代的C1-C4烷基、C6-C10芳基、C6-C10杂芳基。
3.根据权利要求1或2所述的炔基膦酸锡配合物，其特征在于：R2为任选取代的苯基。
4.根据权利要求1-3任意一项所述的炔基膦酸锡配合物，其特征在于：所述任选取代的取代基为卤素，如F、Cl、Br、I，C1-C8烷基，如甲基、乙基、丙基、叔丁基，C1-C8烷氧基，如甲氧基、乙氧基、丙氧基、叔丁氧基，硝基、氰基、三氟甲基；取代基的个数为1、2、3、4、5。
5.权利要求1-4任一项所述的炔基膦酸锡配合物的制备方法，其特征在于：该方法包括：在圆底烧瓶中，加入三正丁基氯化锡和有机溶剂，搅拌，三丁基氯化锡完全溶解后，加入(4-甲氧基苯基)乙炔基磷酸单钠，搅拌反应后，冷却，过滤，滤液减压浓缩，加入适量石油醚并过滤，真空浓缩得产品。
6.根据权利要求5所述的炔基膦酸锡配合物的制备方法，其特征在于：在100mL的圆底烧瓶中，加入3mmol三正丁基氯化锡和20mL无水甲醇，搅拌，三丁基氯化锡完全溶解后，加入3.2mmol(4-甲氧基苯基)乙炔基磷酸单钠，回流下搅拌反应4.5小时，冷却，过滤，滤液减压浓缩，加入适量石油醚并过滤，真空浓缩得产品。
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| CN202010308167.XA CN111333676A (zh) | 2020-04-18 | 2020-04-18 | 一种具有抗肿瘤活性的烃基锡配合物及其制备方法 |
| US17/061,335 US20210017200A1 (en) | 2020-04-18 | 2020-10-01 | Hydrocarbyl Tin Complex with Antitumor Activity and Preparation Method Thereof |
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