5,7-Diallyloxy-2-(3-allyloxy-4-methoxyphenyl)-4H-1-benzopyran-4-one | 178366-78-4

• 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-Diallyloxy-2-(3-allyloxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
• 英文别名: 2-(4-methoxy-3-prop-2-enoxyphenyl)-5,7-bis(prop-2-enoxy)chromen-4-one
• CAS: 178366-78-4
• 化学式: C₂₅H₂₄O₆
• 分子量: 420.462
• InChiKey: QIILCTBEQGPCQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  香叶木素 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以80.4%的产率得到5,7-Diallyloxy-2-(3-allyloxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis, characterization, anti-inflammatory and anti-proliferative activity against MCF-7 cells of O-alkyl and O-acyl flavonoid derivatives

  摘要：

  A series of O-alkyl and O-acyl flavonoid derivatives was synthesized in high efficiency. Alkylation and acylation of 5-hydroxyflavonoids showed that the low reactivity hydroxyl group, 5-OH, well reacted with strong reagents whereas with weaker reagents, the different products were obtained dependently on structural characteristic of ring C of respective flavonoid. In order to evaluate anti-inflammatory activity, all compounds were tested for in vitro inhibition of bovine serum albumin denaturation and in vivo inhibition of carrageenan-induced mouse paw edema. Among them, the compounds 3, 3b, 4b and 4c demonstrated more effective anti-inflammatory activity than standard drugs (diclofenac sodium and ketoprofen) in both tests. Meanwhile, the flavonoids 2, 2c, 3a and 4b displayed anti-proliferative activity against MCF-7 cell lines. Triacetyl derivative of hesperetin 4b inducing degradation of DNA in MCF-7 cells was observed. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.09.005

文献信息

• Diosmetin compounds
  申请人：Adir et Compagnie

  公开号：US05629339A1

  公开（公告）日：1997-05-13

  Disclosed herein are new diosmetin compounds of formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description. The said compounds are useful in the treatment of chronic venous insufficiency.

  本文披露了新的二氧化黄酮化合物，其化学式为：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6如描述中所定义。该化合物在治疗慢性静脉功能不全方面具有用途。
• Dérivés de la diosmétine, leur procédé de préparation et les compositions pharmaceutiques les contenant
  申请人：ADIR ET COMPAGNIE

  公开号：EP0709383B1

  公开（公告）日：1999-12-15
• US5629339A
  申请人：——

  公开号：US5629339A

  公开（公告）日：1997-05-13
• Synthesis, characterization, anti-inflammatory and anti-proliferative activity against MCF-7 cells of O-alkyl and O-acyl flavonoid derivatives
  作者：T. Kim-Dung Hoang、T. Kim-Chi Huynh、Thanh-Danh Nguyen

  DOI：10.1016/j.bioorg.2015.09.005

  日期：2015.12

  A series of O-alkyl and O-acyl flavonoid derivatives was synthesized in high efficiency. Alkylation and acylation of 5-hydroxyflavonoids showed that the low reactivity hydroxyl group, 5-OH, well reacted with strong reagents whereas with weaker reagents, the different products were obtained dependently on structural characteristic of ring C of respective flavonoid. In order to evaluate anti-inflammatory activity, all compounds were tested for in vitro inhibition of bovine serum albumin denaturation and in vivo inhibition of carrageenan-induced mouse paw edema. Among them, the compounds 3, 3b, 4b and 4c demonstrated more effective anti-inflammatory activity than standard drugs (diclofenac sodium and ketoprofen) in both tests. Meanwhile, the flavonoids 2, 2c, 3a and 4b displayed anti-proliferative activity against MCF-7 cell lines. Triacetyl derivative of hesperetin 4b inducing degradation of DNA in MCF-7 cells was observed. (C) 2015 Elsevier Inc. All rights reserved.