CN106699752A - 5-胡椒基-2-吡啶氨基噻唑衍生物作为抗癌药物的应用 - Google Patents
5-胡椒基-2-吡啶氨基噻唑衍生物作为抗癌药物的应用 Download PDFInfo
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Abstract
本发明涉及化学结构式Ⅰ、Ⅱ或Ⅲ所示的5-胡椒基-2-吡啶氨基噻唑衍生物或其盐在制备抗癌药物中的应用：其中，R选自：C1～C2烷基；C3～C4直链烷基或C3～C4支链烷基；R1选自：氢、氘、C1～C2烷基；所述盐选自：盐酸盐、氢溴酸盐、硫酸盐、硝酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐、苹果酸盐、乳酸盐、琥珀酸盐、马来酸盐或富马酸盐。
Description
技术领域
本发明涉及化合物的新用途，具体是5-胡椒基-2-吡啶氨基噻唑衍生物在制备抗癌药物中的应用。
背景技术
中国发明专利[CN 104530035A，2015年4月22日公开]描述了5-胡椒基-4-烷基-2-芳氨基噻唑衍生物或其盐在制备抗农用杀菌剂和杀虫剂中的应用。胡艾希等描述了5-苄基-4-烷基-2-芳氨基噻唑衍生物及其盐在制备抗癌药物中的应用[高等学校化学学报，2013，34(7)：1646～1652；中国发明专利CN 102070556 B，2013年3月20日授权；中国发明专利CN 102319244 A，2012年1月18日公开]。
发明内容
本发明的目的在于提供化学结构式Ⅰ、Ⅱ或Ⅲ所示的5-胡椒基-2-吡啶氨基噻唑衍生物或其盐在制备抗癌药物中的应用：
其中，R选自：C1～C2烷基；C3～C4直链烷基或C3～C4支链烷基；R1选自：氢、氘、C1～C2烷基；所述盐选自：盐酸盐、氢溴酸盐、硫酸盐、硝酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐、苹果酸盐、乳酸盐、琥珀酸盐、马来酸盐或富马酸盐。
本发明的目的在于提供了5-胡椒基-2-吡啶氨基噻唑衍生物选自：5-胡椒基-4-叔丁基-2-(吡啶-2-基氨基)噻唑、5-胡椒基-4-叔丁基-2-(吡啶-3-基氨基)噻唑或5-胡椒基-4-叔丁基-2-(吡啶-4-基氨基)噻唑：
本发明与现有技术相比具有如下优点：
5-胡椒基-2-吡啶氨基噻唑衍生物或其盐具有良好的抗癌活性。
具体实施方式
以下实施例旨在说明本发明而不是对本发明的进一步限定。
实施例1
5-胡椒基-4-叔丁基-2-(吡啶-2-基氨基)噻唑的制备
2mmol 2，2-二甲基-5-(3，4-亚甲二氧基)-4-溴-3-戊酮、2mmol吡啶-2-基硫脲，15mL丙酮，回流8h，反应液用氨水调节pH7，柱层析得到黄色油状物5-胡椒基-4-叔丁基-2-(吡啶-2-基氨基)噻唑，收率60.4％；1H NMR(CDCl3，400MHz)δ:1.40(s，9H，3×CH3)，4.16(s，2H，CH2)，5.94(s，2H，OCH2O)，6.67～7.76(m，3H，C6H3)，7.45(t，J＝8.0Hz，1H，吡啶环-H)，7.58(t，J＝8.0Hz，1H，吡啶环-H)，8.05(d，J＝7.6Hz，1H，吡啶环-H)，8.26(d，J＝4.8.Hz，1H，吡啶环-H)。
实施例2
5-胡椒基-4-叔丁基-2-(吡啶-3-基氨基)噻唑的制备
按实施例1方法制备5-胡椒基-4-叔丁基-2-(吡啶-3-基氨基)噻唑。
实施例3
5-胡椒基-4-叔丁基-2-(吡啶-4-基氨基)噻唑的制备
按实施例1方法制备5-胡椒基-4-叔丁基-2-(吡啶-4-基氨基)噻唑。
实施例4
5-胡椒基-2-吡啶氨基噻唑衍生物(Ⅰ、Ⅱ或Ⅲ)及其盐的制备
其中，R选自：C1～C2烷基；C3～C4直链烷基或C3～C4支链烷基；R1选自：氢、氘、C1～C2烷基；所述盐选自：盐酸盐、氢溴酸盐、硫酸盐、硝酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐、苹果酸盐、乳酸盐、琥珀酸盐、马来酸盐或富马酸盐。
按中国发明专利[CN104530035A，2015.4.22公开]方法制备5-胡椒基-2-吡啶氨基噻唑衍生物。
实施例5
5-胡椒基-2-吡啶氨基噻唑衍生物及其盐的抗肿瘤活性
1.抗肿瘤活性原理
MTT法生物活性测试又称MTT比色法，是一种检测细胞存活和生长的方法。MTT分析法以活细胞代谢物还原剂噻唑蓝[3-(4，5-二甲基-2-噻唑)-2，5-二苯基溴化四氮唑；3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide，MTT]为基础。MTT是一种能接受氢原子的染料。活细胞线粒体中与NADP相关的脱氢酶在细胞内可将黄色的MTT转化成不溶性的蓝紫色的甲瓒(formazon)，而死细胞则无此功能。用DMSO溶解formazon后，在一定波长下用酶标仪测定光密度值，既可定量测出细胞的存活率。根据光密度值的变化观察样品对肿瘤细胞的抑制作用。
2.抗肿瘤活性实验
试样：5-胡椒基-2-吡啶氨基噻唑衍生物(Ⅰ、Ⅱ或Ⅲ)及其盐的制备
其中，R选自：C1～C2烷基；C3～C4直链烷基或C3～C4支链烷基；R1选自：氢、氘、C1～C2烷基；所述盐选自：盐酸盐、氢溴酸盐、硫酸盐、硝酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐、苹果酸盐、乳酸盐、琥珀酸盐、马来酸盐或富马酸盐。
细胞系：宫颈癌细胞系Hela、肺腺癌细胞系A549和乳腺癌细胞系MCF-7(中南大学湘雅医学院细胞库提供)。
试剂：噻唑蓝(MTT)、RPMI 1640培养液、新生牛血清、抗生素(美国英杰生命技术公司)；胰酶(美国AMRESCO公司)；96孔培养板(美国英杰生命技术公司)；二甲基亚砜(美国Sigma公司)。
仪器：HFsafe-1500型超净工作台、HF151UV型CO2培养箱(上海力申科学仪器有限公司)；XSP-15C型倒置显微镜(上海长方光学仪器有限公司)；Multiskan MK3型酶标仪(美国Thermo公司)；超纯水制备仪(美国Milli-Q公司)。
实验操作：试样对Hela细胞、A549细胞和MCF-7细胞的测试。每种细胞的实验操作过程相同，一次实验过程中，每种试样设置5个浓度梯度(0.010μmol/mL、0.030μmol/mL、0.100μmol/mL、0.300μmol/mL和1.000μmol/mL)，每个浓度四个平行试样，每组实验平行3次，并通过空白组对照得出结论。酶标仪检测各孔OD值，检测波长570nm。
3.抗肿瘤活性评价
1)细胞抑制率计算：
2)IC50值计算
试样浓度对数值与细胞抑制率线性回归，利用软件计算试样对细胞的半数抑制浓度IC50值。5-胡椒基-4-叔丁基-2-(吡啶-2-基氨基)噻唑对Hela细胞、A549细胞和MCF-7细胞的IC50分别为4.79±0.86μmol/mL、5.13±0.62μmol/mL和4.71±0.47μmol/mL。
活性测试结果显示，5-胡椒基-2-吡啶氨基噻唑衍生物或其盐对宫颈癌细胞(Hela细胞)、人肺腺癌细胞(A549细胞)和人乳腺癌细胞(MCF-7细胞)具有良好的抑制活性，可用于制备抗肿瘤药物。
Claims (2)
1.化学结构式Ⅰ、Ⅱ或Ⅲ所示的5-胡椒基-2-吡啶氨基噻唑衍生物或其盐在制备抗癌药物中的应用：
其中，R选自：C1～C2烷基；C3～C4直链烷基或C3～C4支链烷基；R1选自：氢、氘、C1～C2烷基；所述盐选自：盐酸盐、氢溴酸盐、硫酸盐、硝酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐、苹果酸盐、乳酸盐、琥珀酸盐、马来酸盐或富马酸盐。
2.权利要求1所述的应用，其中式Ⅰ、Ⅱ或Ⅲ所示的5-胡椒基-2-吡啶氨基噻唑衍生物选自：5-胡椒基-4-叔丁基-2-(吡啶-2-基氨基)噻唑、5-胡椒基-4-叔丁基-2-(吡啶-3-基氨基)噻唑或5-胡椒基-4-叔丁基-2-(吡啶-4-基氨基)噻唑：
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| CN1897814A (zh) * | 2003-12-24 | 2007-01-17 | 拜尔作物科学有限公司 | 植物生长调节作用 |
| US20120172374A1 (en) * | 2010-12-29 | 2012-07-05 | Development Center For Biotechnology | Novel tubulin inhibitors and methods of using the same |
| CN104530036A (zh) * | 2015-01-07 | 2015-04-22 | 湖南大学 | 5-胡椒基-4-烷基-2-苄亚氨基噻唑及其制备方法与应用 |
| CN104530035A (zh) * | 2015-01-07 | 2015-04-22 | 湖南大学 | 5-胡椒基-4-烷基-2-芳氨基噻唑及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1897814A (zh) * | 2003-12-24 | 2007-01-17 | 拜尔作物科学有限公司 | 植物生长调节作用 |
| US20120172374A1 (en) * | 2010-12-29 | 2012-07-05 | Development Center For Biotechnology | Novel tubulin inhibitors and methods of using the same |
| CN104530036A (zh) * | 2015-01-07 | 2015-04-22 | 湖南大学 | 5-胡椒基-4-烷基-2-苄亚氨基噻唑及其制备方法与应用 |
| CN104530035A (zh) * | 2015-01-07 | 2015-04-22 | 湖南大学 | 5-胡椒基-4-烷基-2-芳氨基噻唑及其制备方法与应用 |
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