4',7-bis(2,3-epoxypropoxy)isoflavone | 1268612-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4',7-bis(2,3-epoxypropoxy)isoflavone
• 英文别名: 7-oxiranylmethoxy-3-(4-oxiranylmethoxy-phenyl)-4H-chromen-4-one；7-(Oxiran-2-ylmethoxy)-3-[4-(oxiran-2-ylmethoxy)phenyl]chromen-4-one；7-(oxiran-2-ylmethoxy)-3-[4-(oxiran-2-ylmethoxy)phenyl]chromen-4-one
• CAS: 1268612-83-4
• 化学式: C₂₁H₁₈O₆
• 分子量: 366.37
• InChiKey: FEZJUCJCRGCMPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4',7-bis(2,3-epoxypropoxy)isoflavone 、 二正丙胺 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以65%的产率得到4',7-bis(3-dipropylamino-2-hydroxypropoxy)isoflavone
  参考文献：
  名称：

  替罗龙类似物作为潜在抗癌药的合成和活性评估

  摘要：

  噻洛酮是具有抗癌活性的干扰素诱导剂。通过改进芴酮骨架，侧链和氨基，合成了二十二种新颖的tilorone类似物，以筛选新的抗癌药。体外评估表明，十种新化合物具有比tilorone更好的抗癌活性。其中，图2c（IC 50  <7个μM针对癌细胞系和IC 50  > 35μM对非癌细胞系）和图5d（IC 50  <10μM的对癌症细胞系和IC 50 针对非癌细胞系> 53μM）表现出最佳的抗癌活性和选择性。通过分子操作环境（MOE）对高活性化合物进行了药效学建模，以生成用于化合物设计的可视化模型，以供将来研究之用。

  DOI：

  10.1016/j.ejmech.2013.03.050
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-羟基苯基)-乙酮 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.0h， 生成 4',7-bis(2,3-epoxypropoxy)isoflavone
  参考文献：
  名称：

  Synthetic analogs of daidzein, having more potent osteoblast stimulating effect

  摘要：

  A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.008

文献信息

• BISPHENOL POLYMER PRECURSOR REPLACEMENTS
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20160032043A1

  公开（公告）日：2016-02-04

  Use of biologically-derived polyphenols for the preparation of epoxy resins is described. Examples of biologically-derived polyphenols include resveratrol, genistein, daidzein, and polyphenols synthesized from tyrosine. Because the epoxy resins are prepared from biologically-derived materials, they provide epoxy resins that will degrade into biologically harmless materials. The epoxy resins can be used to provide coating compositions.

  本文描述了使用生物衍生多酚类物质制备环氧树脂的方法。生物衍生多酚类物质的例子包括白藜芦醇、异黄酮、大豆黄酮和从酪氨酸合成的多酚类物质。由于环氧树脂是由生物衍生材料制备而成的，因此它们可以提供会分解为生物无害物质的环氧树脂。这些环氧树脂可以用于制备涂料组合物。
• US9777106B2
  申请人：——

  公开号：US9777106B2

  公开（公告）日：2017-10-03
• [EN] BISPHENOL POLYMER PRECURSOR REPLACEMENTS<br/>[FR] REMPLACEMENTS D'UN PRÉCURSEUR DE POLYMÈRE DE BISPHÉNOL
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2014152714A1

  公开（公告）日：2014-09-25

  Use of biologically-derived polyphenols for the preparation of epoxy resins is described. Examples of biologically-derived polyphenols include resveretrol, genistein, daidzein, and polyphenols synthesized from tyrosine. Because the epoxy resins are prepared from biologically-derived materials, they provide epoxy resins that will degrade into biologically harmless materials. The epoxy resins can be used to provide coating compositions.
• Synthesis and activity evaluation of tilorone analogs as potential anticancer agents
  作者：Dingshan Zhou、Wei Tuo、Hao Hu、Jianrong Xu、Hongzhuan Chen、Zhigang Rao、Yuling Xiao、Xianming Hu、Peng Liu

  DOI：10.1016/j.ejmech.2013.03.050

  日期：2013.6

  Tilorone is an interferon inducer with anticancer activity. Twenty-two novel tilorone analogs were synthesized by improvements of fluorenone skeleton, side chains and amino groups to screen new anticancer agents. In vitro evaluation showed that ten new compounds had better anticancer activities than tilorone. Among them, 2c (IC50 < 7 μM against cancer cell lines and IC50 > 35 μM against non-cancer

  噻洛酮是具有抗癌活性的干扰素诱导剂。通过改进芴酮骨架，侧链和氨基，合成了二十二种新颖的tilorone类似物，以筛选新的抗癌药。体外评估表明，十种新化合物具有比tilorone更好的抗癌活性。其中，图2c（IC 50  <7个μM针对癌细胞系和IC 50  > 35μM对非癌细胞系）和图5d（IC 50  <10μM的对癌症细胞系和IC 50 针对非癌细胞系> 53μM）表现出最佳的抗癌活性和选择性。通过分子操作环境（MOE）对高活性化合物进行了药效学建模，以生成用于化合物设计的可视化模型，以供将来研究之用。
• Synthetic analogs of daidzein, having more potent osteoblast stimulating effect
  作者：Dinesh K. Yadav、Abnish K. Gautam、Jyoti Kureel、Kamini Srivastava、Mahendra Sahai、Divya Singh、Naibedya Chattopadhyay、Rakesh Maurya

  DOI：10.1016/j.bmcl.2010.12.008

  日期：2011.1

  A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein. (C) 2010 Elsevier Ltd. All rights reserved.