2,4-cis-7-hydroxyflavan-4-ol

• 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-hydroxyflavan-4-ol
• 英文别名: (2R,4R)-2-phenyl-3,4-dihydro-2H-chromene-4,7-diol
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: KYPVDKAIGIDYLB-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 2,4-cis-7-hydroxyflavan-4-ol 以 四氢呋喃 为溶剂， 以37%的产率得到2,4-trans-4-imidazolyl-7-hydroxyflavan-4-ol
  参考文献：
  名称：

  Design, synthesis and evaluation of 4-imidazolylflavans as new leads for aromatase inhibition

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(02)00565-6
• 作为产物：
  描述：

  7-羟基黄烷酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以38%的产率得到2,4-cis-7-hydroxyflavan-4-ol
  参考文献：
  名称：

  Flavan-4-ols和4-Methoxyflavans的合成和结构作为新的潜在抗癌药物

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(00)00566-4

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。
• 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.