2,4-cis-7-methoxyflavan-4-ol | 22218-55-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2,4-cis-7-methoxyflavan-4-ol
• 英文别名: (2R,4R)-7-methoxy-2-phenyl-3,4-dihydro-2H-chromen-4-ol
• CAS: 22218-55-9；55539-24-7；63526-99-8；63527-00-4
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: GMKMWNMOLXKFNU-HUUCEWRRSA-N

物化性质

• 沸点：
  419.0±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-cis-7-methoxyflavan-4-ol 在 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 以71%的产率得到7-甲氧基黄酮
  参考文献：
  名称：

  4-黄烷醇和苄型醇的光氧化反应

  摘要：

  在氧气氛下在苯中照射顺式和反式 4- 黄烷醇产生对产率具有显着结构影响的黄烷酮：高顺式/反式选择性和电子给体取代基的增强作用。一系列苄型醇表现出类似的取代作用。根据对中间体有利重叠的立体电子要求来解释结构-反应性关系。为了推断活性氧化剂种类，将上述光反应与单线态氧和超氧离子的氧化进行比较。提出了超氧离子或其相关物种如电子转移络合物R+····O2-·的参与。还研究了添加剂和溶剂的影响。

  DOI：

  10.1246/bcsj.57.1870
• 作为产物：
  描述：

  7-甲氧基黄酮 在 Aspergillus niger KB 作用下， 反应 216.0h， 以76%的产率得到2,4-cis-7-methoxyflavan-4-ol
  参考文献：
  名称：

  Microbial Transformations of 7-Methoxyflavanone

  摘要：

  利用曲霉属（A. niger KB、A. ochraceus 456）和青霉菌（Penicillium chermesinum 113）菌株对外消旋7-美氧黄烷酮的微生物转化进行了描述。A. niger KB菌株催化了羰基的还原，生成了(±)-2,4-cis-7-美氧黄烷-4-醇。借助A. ochraceus 456进行的生物转化得到了两种产物：(+)-2,4-trans-7-美氧黄烷-4-醇和4'-羟基-7-美氧黄酮。通过P. chermesinum 113的转化结果是一个二氢查尔酮产物，即4,2'-二羟基-4'-美氧二氢查尔酮。DPPH清除活性测试表明，所有生物转化产物的抗氧化活性均高于底物。

  DOI：

  10.3390/molecules171214810

文献信息

• Synthesis and Structure of Flavan-4-ols and 4-Methoxyflavans as New Potential Anticancer Drugs
  作者：Christelle Pouget、Catherine Fagnere、Jean-Philippe Basly、Hubert Leveque、Albert-José Chulia

  DOI：10.1016/s0040-4020(00)00566-4

  日期：2000.8

  Reduction of a series of substituted flavanones afforded synthetic access to flavan-4-ols and was followed for some of them by an SN2-type acid-catalysis in methanol to provide 4-methoxyflavans. The stereochemistry of these compounds was established by 1H and 13C NMR data. Flavan-4-ols and 4-methoxyflavans have been resolved into enantiomers which are being evaluated as anticancer drugs.

  一系列得到合成获得黄烷-4-醇和取代的黄烷酮的还原，随后进行由S它们中的一些Ñ在甲醇2类型的酸催化，以提供4- methoxyflavans。这些化合物的立体化学由1 H和13 C NMR数据确定。黄烷-4-醇和4-甲氧基黄烷已被解析为对映体，其被评估为抗癌药。
• Flavonoids: structural requirements for antiproliferative activity on breast cancer cells
  作者：Christelle Pouget、Fabienne Lauthier、Alain Simon、Catherine Fagnere、Jean-Philippe Basly、Christiane Delage、Albert-José Chulia

  DOI：10.1016/s0960-894x(01)00617-5

  日期：2001.12

  Several classes of flavonoids (flavones, flavanones, 2'-hydroxychalcones and flavan-4-ols) having a variety of substituents on A ring were investigated for their antiproliferative activity against MCF-7 human breast cancer cells. Structure-activity relationships of these compounds were discussed. 2'-hydroxychalcones and methoxylated flavanones were found to be potent inhibitors of MCF-7 cells growth

  研究了在A环上具有各种取代基的几类类黄酮（类黄酮，黄烷酮，2'-羟基查耳酮和黄烷-4-醇）对MCF-7人乳腺癌细胞的抗增殖活性。讨论了这些化合物的构效关系。发现2'-羟基查耳酮和甲氧基黄酮是MCF-7细胞生长的有效抑制剂，而黄酮和flavan-4-ols除7,8-二羟基黄酮外似乎是弱抑制剂。
• Synthesis and evaluation of 4-triazolylflavans as new aromatase inhibitors
  作者：Samir Yahiaoui、Christelle Pouget、Catherine Fagnere、Yves Champavier、Gérard Habrioux、Albert José Chulia

  DOI：10.1016/j.bmcl.2004.07.090

  日期：2004.10

  Aromatase is a target of pharmacological interest for the treatment of estrogen-dependent cancers. Azole derivatives such as letrozole or anastrozole have been developed for aromatase inhibition and are used for the treatment of breast tumors. In this paper, four 4-triazolylflavans were synthesized and were found to exhibit moderate to high inhibitory activity against aromatase. (C) 2004 Elsevier Ltd. All rights reserved.
• Design, synthesis and evaluation of 4-imidazolylflavans as new leads for aromatase inhibition
  作者：Christelle Pouget、Catherine Fagnere、Jean-Philippe Basly、Gérard Habrioux、Albert José Chulia

  DOI：10.1016/s0960-894x(02)00565-6

  日期：2002.10

  Two 4-imidazolylflavans were synthesized and their relative stereochemistry was established by H-1 and C-13 NMR data. These compounds were tested for their activity to inhibit aromatase. It was observed that the introduction of an imidazolyl group at carbon 4 on flavan nucleus led to potent molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Bateman, Graham; Brown, Ben R.; Campbell, John B., Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2903 - 2912
  作者：Bateman, Graham、Brown, Ben R.、Campbell, John B.、Cotton, Charles A.、Johnson, Philip、et al.

  DOI：——

  日期：——