5.7.4'-Trimethoxyflavan-4-ol | 10493-01-3

• 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: 5.7.4'-Trimethoxyflavan-4-ol
• 英文别名: 4-hydroxy-5,7,4'-trimethoxyflavan；5,7-dimethoxy-2-(4-methoxy-phenyl)-chroman-4-ol；5,7-dimethoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-4-ol
• CAS: 10493-01-3
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: XCMICCXLNOOUBF-UHFFFAOYSA-N

物化性质

• 熔点：
  159-159.5 °C
• 沸点：
  477.1±45.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5.7.4'-Trimethoxyflavan-4-ol 生成 4-Acetoxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chroman
  参考文献：
  名称：

  黄烷酮及相关化合物；聚羟基黄酮的有色还原产物。

  摘要：

  DOI：

  10.1021/ja01208a052
• 作为产物：
  描述：

  4',5,7-trimethoxyflavanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以76%的产率得到5.7.4'-Trimethoxyflavan-4-ol
  参考文献：
  名称：

  Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.03.054

文献信息

• Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents
  申请人：——

  公开号：US20030229136A1

  公开（公告）日：2003-12-11

  Novel compounds useful as chemotherapeutic, chemopreventive, and antiangiogenic agents are provided. The compounds are flavanoids, including flavanones, flavanols, and chalcones. The compounds have the structure of formula (I) 1 wherein R 1 through R 3 and R 5 through R 11 are defined herein, and &agr;, &bgr; and &ggr; are optional bonds, providing that when &agr; is absent, &bgr; is present, and when &bgr; is absent, &agr; is present. When &agr; is present, preferred R 4 moieties are selected from O, S, NH and CH 2 , and when &agr; is absent, preferred R 4 groups are selected from OH, SH, NH 2 and CH 3 . When &ggr; is present, the preferred R 5 substituent is O, while when &ggr; is absent, the preferred R 5 substituent is OH. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.

  提供了作为化疗、化学预防和抗血管生成的有用化合物。这些化合物是类黄酮类化合物，包括黄酮酮、黄烷醇和香豆素。这些化合物具有公式（I）的结构，其中R1至R3和R5至R11在此定义，α、β和γ为可选键，当α不存在时，β存在，当β不存在时，α存在。当α存在时，首选的R4基团从O、S、NH和CH2中选择，当α不存在时，首选的R4基团从OH、SH、NH2和CH3中选择。当γ存在时，首选的R5取代基是O，而当γ不存在时，首选的R5取代基是OH。还提供了药物组合物，以及合成和使用方法。
• US7329687B2
  申请人：——

  公开号：US7329687B2

  公开（公告）日：2008-02-12