2,3-dimethoxy-4,5-methylenedioxybenzyl alcohol | 1291486-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2,3-dimethoxy-4,5-methylenedioxybenzyl alcohol
• 英文别名: (6,7-Dimethoxy-1,3-benzodioxol-5-yl)methanol
• CAS: 1291486-39-9
• 化学式: C₁₀H₁₂O₅
• mdl: MFCD23703727
• 分子量: 212.202
• InChiKey: BSXSTVQMWZEPBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-4,5-methylenedioxybenzyl alcohol 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 0.67h， 生成 6-(chloromethyl)-4,5-dimethoxybenzo[d][1,3]dioxole
  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：

  2,3-dimethoxy-4,5-methylenedioxybenzaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以88.4%的产率得到2,3-dimethoxy-4,5-methylenedioxybenzyl alcohol
  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

• <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.