Apiolsaeure-methylester | 109844-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Apiolsaeure-methylester
• 英文别名: Methyl 4,7-dimethoxy-1,3-benzodioxole-5-carboxylate
• CAS: 109844-90-8
• 化学式: C₁₁H₁₂O₆
• mdl: MFCD09261478
• 分子量: 240.213
• InChiKey: OFWWVWJAFWAQEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  76.5-77.5 °C
• 沸点：
  156-158 °C(Press: 2 Torr)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Apiolsaeure-methylester 在 盐酸肼 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 0.5h， 生成 4-(4-methoxyphenyl)-5-(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 、 氯化亚砜 、 四丁基溴化铵 、 过氧化脲素 、 臭氧 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 5.17h， 生成 Apiolsaeure-methylester
  参考文献：
  名称：

  Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

  摘要：

  DOI：

  10.1021/np1004278

文献信息

• Dill and parsley seed extracts in scale up synthesis of aminopolyalkoxybenzenes – beneficial synthons for fused nitrogen polyalkoxyheterocycles
  作者：Irina B. Karmanova、Sergei I. Firgang、Leonid D. Konyushkin、Victor N. Khrustalev、Alexander V. Ignatov、Leonid A. Kuznetsov、Yuriy A. Pinchuk、Ivan A. Kozlov、Victor V. Semenov

  DOI：10.1016/j.mencom.2016.01.026

  日期：2016.1

  Ecologically friendly transformation of readily accessible plant allylpolyalkoxybenzenes to hardly available aminotetraalkoxybenzenes has been developed. The efficacy of hydrogenation stage is substantially increased by the application of highly porous ceramic block Pd-catalysts featuring a large surface area, low hydraulic resistance, significant thermal and mechanical stabililty, multiple cycling and easy regeneration.
• Ciamician; Silber, Chemische Berichte, 1888, vol. 21, p. 1623,1624
  作者：Ciamician、Silber

  DOI：——

  日期：——
• Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes
  作者：Victor V. Semenov、Alex S. Kiselyov、Ilia Y. Titov、Irina K. Sagamanova、Natalie N. Ikizalp、Natalia B. Chernysheva、Dmitry V. Tsyganov、Leonid D. Konyushkin、Sergei I. Firgang、Roman V. Semenov、Irina B. Karmanova、Mikhail M. Raihstat、Marina N. Semenova

  DOI：10.1021/np1004278

  日期：2010.11.29
• <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.