echioidinin | 4308-56-9

• 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: echioidinin
• 英文别名: 5,2'-dihydroxy-7-methoxyflavone；5-hydroxy-2-(2-hydroxyphenyl)-7-methoxychromen-4-one
• CAS: 4308-56-9
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: PXFLNHWWYOVFDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2',6'-trihydroxy-4'-methoxychalcone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以58.7%的产率得到echioidinin
  参考文献：
  名称：

  Synthesis, growth inhibition, and cell cycle evaluations of novel flavonoid derivatives

  摘要：

  As a continuation of our search for potential new anticancer agents, a series of ten flavonoid derivatives has been synthesized by cyclization of substituted chalcones. Target compounds were evaluated for their biological activity. Among them, compounds 1-4 and 9 displayed a significant growth inhibitory action against a panel of tumor cell lines including Jurkat, PC-3, and Colon 205. On treatment with an equitoxic (IC50) concentration, compounds 1-5 and 7-9 blocked cells in the G2/M phase of the Jurkat cell cycle, whereas compound 6 blocked the same in the G0/G1 phase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.062

文献信息

• Dihydroechioidinin, a flavanone from Andrographis echioides
  作者：B Jayaprakasam、A.G Damu、D Gunasekar、A Blond、B Bodo

  DOI：10.1016/s0031-9422(99)00295-2

  日期：1999.11

  A reinvestigation of the whole plant of Andrographis echioides has led to the isolation of a new flavanone, dihydroechioidinin together with four known flavones, echioidinin, echioidin, skullcapflavone I 2'-O-methyl ether, and skullcapflavone I 2'-O-glucoside. The structure of dihydroechioidinin was established as (2S)-5,2'-dihydroxy-7-methoxyflavanone on the basis of spectral and chemical evidence. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A flavone glycoside from Andrographis alata
  作者：A.G. Damu、B. Jayaprakasam、K.V. Rao、D. Gunasekar

  DOI：10.1016/s0031-9422(98)00342-2

  日期：1998.11

  A new flavone glycoside, echioidinin 5-glucoside along-with its known aglycone, echioidinin have been isolated from the whole plant of Andrographis alata. The structure of the new compound was established as 5,2'-dihydroxy-7-methoxyflavone 5-O-beta-D-glucopyranoside on the basis of spectral and chemical studies. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.