5,5'-{3,3'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropoxy}bis(5-oxopentanoic acid)

• 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: 5,5'-{3,3'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropoxy}bis(5-oxopentanoic acid)
• 英文别名: 5-[3-[3-[3-(4-Carboxybutanoyloxy)propoxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochromen-7-yl]oxypropoxy]-5-oxopentanoic acid；5-[3-[3-[3-(4-carboxybutanoyloxy)propoxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochromen-7-yl]oxypropoxy]-5-oxopentanoic acid
• 化学式: C₃₇H₄₄O₁₄
• 分子量: 712.748
• InChiKey: KBGYLQGPALMHIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  51
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  201
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  去水淫羊藿黄素 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 14.0h， 生成 5,5'-{3,3'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropoxy}bis(5-oxopentanoic acid)
  参考文献：
  名称：

  Synthesis and cancer cell growth inhibitory activity of icaritin derivatives

  摘要：

  A series of icaritin derivatives bearing carboxylic acid or carboxylic ester groups are synthesized, and their in vitro cytotoxic activity against three cancer cell lines, MCF-7, MDA-MB-435s, and A549, are evaluated by MTT assay. Several derivatives including 2h, 2j, 5b and 5d show higher cytotoxic activity than the parent compound icaritin against these cancer cell lines. Compounds 5b and 5d are even more cytotoxic to MCF-7 cells than the clinic drug tamoxifen. Moreover, compound 5b is found to be non-toxic to normal cells (Vero) and both 5b and 5d exhibit good selectivity towards estrogen receptor positive MCF-7 breast cancer cells over estrogen receptor negative MDA-MB-435s breast cancer cells. The structure activity relationship analysis has revealed that mono-substitution at either C-3 or C-7 hydroxyl group of icaritin could improve the cytotoxicity of icaritin, and the C-3 hydroxyl group may be a preferable site for chemical modification. In addition, the length, the flexibility and the additional branching substituent group of the substitution chain(s) at both C-3 and C-7 hydroxyl groups can all affect the anticancer activity of these derivatives. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.006

文献信息

• 淫羊藿素衍生物及其制备方法和用途
  申请人：中国科学院华南植物园

  公开号：CN104610212B

  公开（公告）日：2017-04-26

  本发明公开了淫羊藿素衍生物及其制备方法和用途。淫羊藿素衍生物，其结构如式(1)表示，其中，化合物1：m＝2，n＝3；或化合物2：m＝3，n＝3。本发明的淫羊藿素衍生物水溶性更好，抗肿瘤活性更强，对正常细胞毒性更低，能用于制备抗肿瘤药物，具有广泛的应用前景。
• Synthesis and cancer cell growth inhibitory activity of icaritin derivatives
  作者：Chen Wang、Ping Wu、Jing-Fang Shi、Zi-Hua Jiang、Xiao-Yi Wei

  DOI：10.1016/j.ejmech.2015.06.006

  日期：2015.7

  A series of icaritin derivatives bearing carboxylic acid or carboxylic ester groups are synthesized, and their in vitro cytotoxic activity against three cancer cell lines, MCF-7, MDA-MB-435s, and A549, are evaluated by MTT assay. Several derivatives including 2h, 2j, 5b and 5d show higher cytotoxic activity than the parent compound icaritin against these cancer cell lines. Compounds 5b and 5d are even more cytotoxic to MCF-7 cells than the clinic drug tamoxifen. Moreover, compound 5b is found to be non-toxic to normal cells (Vero) and both 5b and 5d exhibit good selectivity towards estrogen receptor positive MCF-7 breast cancer cells over estrogen receptor negative MDA-MB-435s breast cancer cells. The structure activity relationship analysis has revealed that mono-substitution at either C-3 or C-7 hydroxyl group of icaritin could improve the cytotoxicity of icaritin, and the C-3 hydroxyl group may be a preferable site for chemical modification. In addition, the length, the flexibility and the additional branching substituent group of the substitution chain(s) at both C-3 and C-7 hydroxyl groups can all affect the anticancer activity of these derivatives. (C) 2015 Elsevier Masson SAS. All rights reserved.