isomyristicin | 487-62-7

• 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: isomyristicin
• 英文别名: 3,4-Methylendioxy-5-methoxy-1-propenylbenzol；4-methoxy-6-prop-1-enyl-1,3-benzodioxole
• CAS: 487-62-7
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD00016901
• 分子量: 192.214
• InChiKey: DHUZAAUGHUHIDS-UHFFFAOYSA-N

物化性质

• 沸点：
  289.3±9.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isomyristicin 在 吡啶 、 ammonium hydroxide 、 氯化亚砜 、 碘 、 臭氧 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 29.0h， 生成 7-methoxybenzo[d][1,3]dioxole-5-carbohydrazide
  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：

  肉豆蔻醚 在 potassium hydroxide 作用下， 反应 0.67h， 生成 isomyristicin
  参考文献：
  名称：

  植物聚烷氧基苯衍生物的氢化：方便获得辅酶Q0类似物

  摘要：

  已经开发出技术上先进的方案，用于将植物烯丙基（聚烷氧基）苯转化为甲基和丙基（聚烷氧基）苯，它们是辅酶Q0类似物合成中的中间体。烯丙基和苯甲醛部分氢化的关键阶段是以周期性的高压釜模式在高度多孔的陶瓷嵌段Pd催化剂上进行的。这些催化剂具有大的表面积，低的水力阻力，显着的热稳定性和机械稳定性，多次循环和易于再生，可显着减少Pd的消耗。

  DOI：

  10.1016/j.mencom.2020.09.015

文献信息

• Pseudonitrosites as masked nitroalkenes in the Barton–Zard pyrrole synthesis
  作者：Daniil A. Rusanov、Andrey B. Myshlyavtsev、Eugenia A. Silyanova、Alexander V. Samet、Victor V. Semenov

  DOI：10.1016/j.mencom.2020.07.026

  日期：2020.7

  3-Aryl-4-methylpyrrole-2-carboxylates were prepared via the Barton–Zard reaction using pseudonitrosites as a source of the corresponding nitroalkenes. The starting pseudonitrosites were, in turn, obtained via addition of N2O3 to propenylbenzenes available from the natural plant essential oils.

  3-Baryl-4-吡咯-2-甲酸3-芳基酯是通过使用伪亚硝酸盐作为相应硝基烯烃的来源的Barton-Zard反应制备的。反过来，通过将N2O3加到可从天然植物精油中得到的丙烯基苯中获得起始假亚硝酸盐。
• Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents
  作者：Natalia B. Chernysheva、Dmitry V. Tsyganov、Alex A. Philchenkov、Michael P. Zavelevich、Alex S. Kiselyov、Roman V. Semenov、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2012.01.128

  日期：2012.4

  A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3',5'-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity. (C) 2012 Elsevier Ltd. All rights reserved.
• <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.
• 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.