dillapiolic acid | 22027-56-1

• 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: dillapiolic acid
• 英文别名: dillapionic acid；6,7-dimethoxy-benzo[1,3]dioxole-5-carboxylic acid；6,7-Dimethoxy-benzo[1,3]dioxol-5-carbonsaeure；Dillapiolsaeure；6,7-Dimethoxy-1,3-benzodioxole-5-carboxylic acid
• CAS: 22027-56-1
• 化学式: C₁₀H₁₀O₆
• mdl: MFCD09028348
• 分子量: 226.186
• InChiKey: FRDRMVXVIUVAPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  dillapiolic acid 在 氯化亚砜 、 sodium methylate 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 3-(3-hydroxy-4-methoxyphenyl)-5-(2,3-dimethoxy-4,5-methylenedioxyphenyl)-1,2,4-triazole
  参考文献：
  名称：

  Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

  摘要：

  DOI：

  10.1021/np1004278
• 作为产物：
  描述：

  2,3-dimethoxy-4,5-methylenedioxybenzaldehyde 在 过氧化脲素 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以87%的产率得到dillapiolic acid
  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

• 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.
• 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.
• Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues
  作者：Ilia Y. Titov、Irina K. Sagamanova、Roman T. Gritsenko、Irina B. Karmanova、Olga P. Atamanenko、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2011.01.124

  日期：2011.3

  Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.
• Ciamician; Silber, Chemische Berichte, 1896, vol. 29, p. 1804
  作者：Ciamician、Silber

  DOI：——

  日期：——