CN102060757A - 酰腙类Schiff碱化合物及其制备方法与应用 - Google Patents

酰腙类Schiff碱化合物及其制备方法与应用 Download PDF

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CN102060757A
CN102060757A CN2010105871960A CN201010587196A CN102060757A CN 102060757 A CN102060757 A CN 102060757A CN 2010105871960 A CN2010105871960 A CN 2010105871960A CN 201010587196 A CN201010587196 A CN 201010587196A CN 102060757 A CN102060757 A CN 102060757A
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schiff alkali
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acylhydrazone
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CN102060757B (zh
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尹汉东
魏新庭
张启俊
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Liaocheng University
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Abstract

本发明公开了一种酰腙类Schiff碱化合物，结构式如下：

Description

酰腙类Schiff碱化合物及其制备方法与应用
技术领域
本发明涉及一种酰腙类Schiff碱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
酰腙类Schiff碱有机化合物因其良好的配位能力引起了人们的广泛兴趣，人们在对有机抗癌药物的研究和筛选过程中，发现一些酰腙类Schiff碱有机化合物较高的抗肿瘤活性。此后，随着人们对酰腙类Schiff碱化合物的研究不断深入，酰腙类Schiff碱化合物的研究领域和应用范围也随之不断扩大。
发明内容
针对上述现有技术，本发明提供了一种新的有机酰腙类Schiff碱化合物，并提供了该化合物的制备方法及其应用。
一种酰腙类Schiff碱化合物，结构式如下：
Figure BDA0000038144330000011
所述酰腙类Schiff碱化合物的制备方法：向烧瓶中加入10mmol的邻香草醛、10～15mmol的2-吡啶酰肼、30ml的乙醇，在温度为50～70℃范围内，搅拌回流2～3小时，旋转蒸发去除约25ml的溶剂，静置过夜，得到大量晶状物，用0℃冰冻乙醇淋洗，自然干燥，乙醇重结晶，得到无色透明晶体，即为酰腙类Schiff碱化合物。
反应式为：
Figure BDA0000038144330000012
所述酰腙类Schiff碱化合物在制备治疗肝癌、肺腺癌、乳腺癌、前列腺癌、结肠癌或早幼粒白血病的药物中的应用。本发明的酰腙类Schiff碱化合物分子式为C13H13N3O3，分子量为259.2607，具有较高的抗癌活性，可以以其为原料制备治疗肝癌、肺腺癌、乳腺癌、前列腺癌、结肠癌和早幼粒白血病的药物。与目前普遍使用的铂类抗癌相比，本发明的酰腙类Schiff碱化合物具有抗癌活性高、脂溶性好、成本低、制备方法简单环保等特点，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：制备酰腙类Schiff碱化合物：向烧瓶中加入10mmol的邻香草醛、10mmol的2-吡啶酰肼、30ml的乙醇，在温度为50℃范围内，搅拌回流2小时，旋转蒸发去除约25ml溶剂，静置过夜，得到大量晶状物，用0℃冰冻乙醇淋洗，自然干燥，乙醇重结晶，得到无色透明晶体，即为酰腙类Schiff碱化合物。产率96％，熔点175～177℃。
经红外光谱分析和核磁共振分析，结果如下：IR(KBr，cm-1)：v(O-H)3448.8w，v(N-H)3271.9s，v(Ar-H)3066.4m，vas(-CH3)2971.4s，vs(-CH3)2840s，v(C＝O)1677.7s，v(C＝N)1607.9s，v(C-O)1299.8m，v(N-N)1043.1w，v(pyridine-H)998.2m，619.3m，402.5w；
1H核磁(400.15MHz，CDCl3，ppm)：δ11.148，(1H，-OH)，10.973(s，1H，-NH)，6.872-6.980(m，3H，Ar-H)，7.508-8.306(m，4H，pyridine-H)，8.608(s，1H，-CH＝N)，3.948(s，3H，-OCH3)。13C核磁(100.62MHz，CDCl3，ppm)：δ159.654(O＝C-N)，114.02，117.718，122.557，122.846，148.383，151.04(aromatic carbons)，119.044，126.7，137.714，148.383，148.726(pyridine carbons)148.139(CH＝N-)，56.241(-OCH3)。
元素分析：C13H13N3O3计算值C，61.99；H，4.83；N，15.41％；实测值C，61.95；，4.92；N，15.37％。
实施例2：制备酰腙类Schiff碱化合物物：向烧瓶中加入10mmol的邻香草醛、14mmol的2-吡啶酰肼、30ml的乙醇，在温度为50℃范围内，搅拌回流2小时，旋转蒸发去除约25ml溶剂，静置过夜，得到大量晶状物，用0℃冰冻乙醇淋洗，自然干燥，乙醇重结晶，得到无色透明晶体，即为酰腙类Schiff碱化合物。产率95％，熔点175～177℃。
实施例3：制备酰腙类Schiff碱化合物：向烧瓶中加入10mmol的邻香草醛、10mmol的2-吡啶酰肼、30ml的乙醇，在温度为70℃范围内，搅拌回流2小时，旋转蒸发去除25ml溶剂，静置过夜，得到大量晶状物，用0℃冰冻乙醇淋洗，自然干燥，乙醇重结晶，得到无色透明晶体，即为酰腙类Schiff碱化合物。产率94％，熔点175～177℃。
试验例：本发明的酰腙类Schiff碱化合物，其体外抗癌活性测定是通过SRB两种实验方法实现的，其原理为：
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分析法对人肝癌细胞株SMMC-7721，人肺腺癌细胞株A549，人乳腺癌细胞株MCF-7，人前列腺癌胞PC-3M，人结肠癌细胞株HCT-8，人早幼粒白血病细胞株HL60(悬浮细胞)，进行分析，测定其IC50值，结果见表1，结论为：根据表中数据可知，本发明的抗癌药物，对人肝癌，人肺腺癌，人乳腺癌，人前列腺癌，人结肠癌，人早幼粒白血病(悬浮细胞)具有良好的的抗癌活性，可作为抗癌药物的候选化合物。
表1酰腙类Schiff碱化合物抗癌药物体外活性测试数据
Figure BDA0000038144330000031

Claims (3)

1.酰腙类Schiff碱化合物，结构式如下：
Figure FDA0000038144320000011
2.权利要求1所述的酰腙类Schiff碱化合物的制备方法，其特征在于：向反应容器中加入10mmol的邻香草醛、10～15mmol的2-吡啶酰肼、30ml的乙醇，在温度为50～70℃范围内，搅拌回流2～3小时，旋转蒸发去除溶剂，静置过夜，得到晶状物，用冰冻乙醇淋洗，自然干燥，乙醇重结晶，得到无色透明晶体，即为酰腙类Schiff碱化合物。
3.权利要求1所述的酰腙类Schiff碱化合物在制备治疗肝癌、肺腺癌、乳腺癌、前列腺癌、结肠癌或早幼粒白血病的药物中的应用。
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CN104546843A (zh) * 2015-01-28 2015-04-29 山东大学齐鲁医院 一种吡唑酰腙衍生物在制备抗乳腺癌药物中的应用
CN104546844A (zh) * 2015-01-28 2015-04-29 山东大学 (e)-n-胡椒基-1-(3-(6-氯吡啶)甲基)- 3-（4-甲氧基苯基）-1h-吡唑-5-碳酰肼的应用
CN110128343A (zh) * 2019-06-18 2019-08-16 四川省人民医院 一种酰肼类化合物

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TWI586641B (zh) * 2016-04-13 2017-06-11 國立中興大學 雙鑭系金屬錯合物、其製備方法、其用途、聚碳酸酯及聚碳酸酯的製造方法

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CN104546844A (zh) * 2015-01-28 2015-04-29 山东大学 (e)-n-胡椒基-1-(3-(6-氯吡啶)甲基)- 3-（4-甲氧基苯基）-1h-吡唑-5-碳酰肼的应用
CN110128343A (zh) * 2019-06-18 2019-08-16 四川省人民医院 一种酰肼类化合物

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