3-(4-methoxyphenyl)-3-oxo-2-(2,5-dimethoxy-3,4-methylenedioxyphenyl)propanenitrile | 1282474-10-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-methoxyphenyl)-3-oxo-2-(2,5-dimethoxy-3,4-methylenedioxyphenyl)propanenitrile
• 英文别名: 2-(4,7-Dimethoxy-1,3-benzodioxol-5-yl)-3-(4-methoxyphenyl)-3-oxopropanenitrile
• CAS: 1282474-10-5
• 化学式: C₁₉H₁₇NO₆
• 分子量: 355.347
• InChiKey: DXZGHYMYIWEYPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-3-oxo-2-(2,5-dimethoxy-3,4-methylenedioxyphenyl)propanenitrile 在 盐酸肼 作用下， 以 乙醇 为溶剂， 以35%的产率得到5-(4-methoxyphenyl)-4-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-1H-pyrazol-3-amine
  参考文献：
  名称：

  cis-Restricted 3-Aminopyrazole Analogues of Combretastatins: Synthesis from Plant Polyalkoxybenzenes and Biological Evaluation in the Cytotoxicity and Phenotypic Sea Urchin Embryo Assays

  摘要：

  We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl-3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multidrug-resistant cancer cells.

  DOI：

  10.1021/np400310m
• 作为产物：
  描述：

  洋芹脑 在 吡啶 、 sodium tetrahydroborate 、 二苯并-18-冠醚-6 、 氯化亚砜 、 sodium hydride 、 臭氧 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙腈 、 mineral oil 、 苯 为溶剂， 反应 11.84h， 生成 3-(4-methoxyphenyl)-3-oxo-2-(2,5-dimethoxy-3,4-methylenedioxyphenyl)propanenitrile
  参考文献：
  名称：

  cis-Restricted 3-Aminopyrazole Analogues of Combretastatins: Synthesis from Plant Polyalkoxybenzenes and Biological Evaluation in the Cytotoxicity and Phenotypic Sea Urchin Embryo Assays

  摘要：

  We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl-3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multidrug-resistant cancer cells.

  DOI：

  10.1021/np400310m

文献信息

• 3-(5-)-Amino-o-diarylisoxazoles: Regioselective synthesis and antitubulin activity
  作者：Dmitry V. Tsyganov、Victor N. Khrustalev、Leonid D. Konyushkin、Mikhail M. Raihstat、Sergei I. Firgang、Roman V. Semenov、Alex S. Kiselyov、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.ejmech.2013.12.006

  日期：2014.2

  materials for the synthetic scheme were easily available from plant extracts. The targeted molecules were further tested in the phenotypic sea urchin embryo assay to identify compounds with antimitotic microtubule destabilizing activity. Structure–activity relationship studies suggested that the structural features essential for potent antiproliferative activity include: 1) 5-aminoisoxazole bridge linking

  已经验证了被聚烷氧基芳基药效基团取代的5-氨基-和3-氨基二芳基异恶唑的区域选择性合成。合成方案的起始原料很容易从植物提取物中获得。在表型海胆胚胎试验中进一步测试了目标分子，以鉴定具有抗有丝分裂微管去稳定活性的化合物。结构与活性之间的关系研究表明，有效的抗增殖活性必不可少的结构特征包括：1）5-氨基异恶唑桥联双芳基取代基（环A和B）；2）未取代的5-氨基；3）3,4,5-甲氧基取代的苯和4-甲氧基苯的药效基团分别作为环A和B。
• <i>cis</i>-Restricted 3-Aminopyrazole Analogues of Combretastatins: Synthesis from Plant Polyalkoxybenzenes and Biological Evaluation in the Cytotoxicity and Phenotypic Sea Urchin Embryo Assays
  作者：Dmitry V. Tsyganov、Leonid D. Konyushkin、Irina B. Karmanova、Sergei I. Firgang、Yuri A. Strelenko、Marina N. Semenova、Alex S. Kiselyov、Victor V. Semenov

  DOI：10.1021/np400310m

  日期：2013.8.23

  We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl-3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multidrug-resistant cancer cells.