3-苄氧基-5,7-二羟基-3,4-二甲氧基黄酮 | 62507-01-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3-苄氧基-5,7-二羟基-3,4-二甲氧基黄酮
• 英文名称: 2-(3-benzyloxy-4-methoxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-one
• 英文别名: 2-(3-Benzyloxy-4-methoxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on；3'-BENZYLOXY-5,7-DIHYDROXY-3,4'-DIMETHOXYFLAVONE；5,7-dihydroxy-3-methoxy-2-(4-methoxy-3-phenylmethoxyphenyl)chromen-4-one
• CAS: 62507-01-1
• 化学式: C₂₄H₂₀O₇
• 分子量: 420.419
• InChiKey: JPEXDMDZYIHQEF-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

ADMET

代谢

3p-苯甲氧基-5,7-二羟基-3,4p-二甲氧基黄酮已知的人类代谢物包括3p-苯甲氧基-5-羟基-3,4p-二甲氧基黄酮和7-O-葡萄糖苷酸。

3p-Benzyloxy-5,7-dihydroxy-3,4p-dimethoxyflavone has known human metabolites that include 3p-Benzyloxy-5-hydroxy-3,4p-dimethoxyflavone, 7-O-glucuronide.

来源:NORMAN Suspect List Exchange

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  3-苄氧基-5,7-二羟基-3,4-二甲氧基黄酮 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.5h， 生成 7-Ethoxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxychromen-4-one
  参考文献：
  名称：

  Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin

  摘要：

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

  DOI：

  10.1021/jm970842h
• 作为产物：
  描述：

  2-甲氧基-1-(2,4,6-三羟基苯基)乙酮 、 3-benzyloxy-4-methoxy-benzoic acid-anhydride 在 potassium 3-(benzyloxy)-4-methoxybenzoate 作用下， 以33%的产率得到3-苄氧基-5,7-二羟基-3,4-二甲氧基黄酮
  参考文献：
  名称：

  Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin

  摘要：

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

  DOI：

  10.1021/jm970842h

文献信息

• Tire with rubber containing flavone
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP1391327A1

  公开（公告）日：2004-02-25

  The invention relates to a rubber composition and a pneumatic tire having a component comprising a rubber containing the reaction product of a flavone and a methylene donor.

  本发明涉及一种橡胶组合物和充气轮胎，其成分包括含有黄酮和亚甲基供体反应产物的橡胶。
• Rubber composition and tire with rubber containing flavone
  申请人：The Goodyear Tire & Rubber Company

  公开号：EP2730431A1

  公开（公告）日：2014-05-14

  A rubber composition comprising a diene based elastomer and an adhesion promoter derived from a flavone, a methylene donor and a methylene acceptor is disclosed. The rubber composition is essentially free of cobalt. Also, a pneumatic tire comprising such a rubber composition is disclosed.

  本发明公开了一种橡胶组合物，该组合物包含一种二烯基弹性体和一种由黄酮、亚甲基供体和亚甲基受体衍生的附着力促进剂。该橡胶组合物基本上不含钴。此外，还公开了一种包含这种橡胶组合物的充气轮胎。
• Methods For Treating Wounds
  申请人：Kimberly-Clark Worldwide, Inc.

  公开号：US20030125264A1

  公开（公告）日：2003-07-03

  Pharmaceutical compositions, and methods of using the same, are provided utilizing effective amounts of one or more flavones, flavonols, flavanones, isoflavanones and isoflavones to increase cell proliferation in various tissues and cell lines. As examples, the composition and methods of the present invention can be used to increase proliferation of fibroblast cells and, more particularly, in the treatment of wounds as well as strengthening of the skin.

  本发明提供了利用有效量的一种或多种黄酮、黄酮醇、黄烷酮、异黄烷酮和异黄酮来增加各种组织和细胞系的细胞增殖的药物组合物及其使用方法。举例来说，本发明的组合物和方法可用于增加成纤维细胞的增殖，特别是用于治疗伤口和强化皮肤。
• King et al., Journal of the Chemical Society, 1952, p. 96,100
  作者：King et al.

  DOI：——

  日期：——
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.