4-hydroxy-5,7-dimethoxyflavan | 42508-82-7

• 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: 4-hydroxy-5,7-dimethoxyflavan
• 英文别名: 3,4-Dihydro-5,7-dimethoxy-2-phenyl-2H-1-benzopyran-4-ol；5,7-dimethoxy-2-phenyl-3,4-dihydro-2H-chromen-4-ol
• CAS: 42508-82-7
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: CWYZJSXIDDQYEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,7-二甲氧基磺烷酮 在 sodium tetrahydroborate 作用下， 生成 4-hydroxy-5,7-dimethoxyflavan
  参考文献：
  名称：

  类黄酮：对乳腺癌细胞抗增殖活性的结构要求。

  摘要：

  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。

  DOI：

  10.1016/s0960-894x(01)00617-5

文献信息

• 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。
• Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora
  作者：Chavi Yenjai、Suchana Wanich

  DOI：10.1016/j.bmcl.2010.03.054

  日期：2010.5

  Flavones 1-4 isolated from Kaempferia parviflora were used for structural modification. Sixteen flavonoid derivatives, including four new derivatives, were synthesized and evaluated for cytotoxicity against KB and NCI-H187 cell lines. Flavanones 2a-4a demonstrated higher cytotoxic activity than the parent compounds. Cytotoxicity against KB cell line of oxime 1c was about 7 times higher than the ellipticine standard. Interestingly, oximes 1c and 2c exhibited highly potent cytotoxicity against NCI-H187 cell line with IC50 values of 0.014 and 0.23 mu M, respectively. Oximes 4c and 5c showed strong cytotoxicity against NCI-H187 cell line with IC50 values of 4.04 and 2.32 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.