3-methyl-8-(2-phenylethyliminomethyl)-5-propan-2-yl-2-[1,6,7-trihydroxy-3-methyl-8-(2-phenylethyliminomethyl)-5-propan-2-ylnaphthalen-2-yl]naphthalene-1,6,7-triol | 6974-00-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-methyl-8-(2-phenylethyliminomethyl)-5-propan-2-yl-2-[1,6,7-trihydroxy-3-methyl-8-(2-phenylethyliminomethyl)-5-propan-2-ylnaphthalen-2-yl]naphthalene-1,6,7-triol
• CAS: 6974-00-1
• 化学式: C₄₆H₄₈N₂O₆
• 分子量: 724.897
• InChiKey: IOMXQZQZJSROPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  146
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-(-)-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthyl-8,8'-dicarbaldehyde 、 2-苯乙胺 以 甲苯 为溶剂， 反应 2.0h， 以73%的产率得到3-methyl-8-(2-phenylethyliminomethyl)-5-propan-2-yl-2-[1,6,7-trihydroxy-3-methyl-8-(2-phenylethyliminomethyl)-5-propan-2-ylnaphthalen-2-yl]naphthalene-1,6,7-triol
  参考文献：
  名称：

  Chiral gossypol derivatives: Evaluation of their anticancer activity and molecular modeling

  摘要：

  To better use gossypol to find promising anticancer compounds, a series of new and known bis-Schiff base analogs of chiral gossypol were synthesized, and their anticancer activity on HeLa, U87 and M85 cells was tested. The results showed that through a simple chemical modification, less active (+)-gossypol could be converted into more active derivatives. When compared with (-)-gossypol, many more potent compounds that could be the promising anticancer agents were found, and some of them were more potent than the anticancer drug Cisplatin against all three cancer cell lines. By eliminating target functional groups, we observed that the major contributor to the anticancer activity of chiral gossypol seemed to be the phenolic groups, and not the aldehyde groups. Through comprehensive analysis of chiral gossypol analogs, the structure-activity relationships were elaborated. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.025

文献信息

• Chiral gossypol derivatives: Evaluation of their anticancer activity and molecular modeling
  作者：Long Zhang、Haixia Jiang、Xingxin Cao、Huiyun Zhao、Fan Wang、Yuxin Cui、Biao Jiang

  DOI：10.1016/j.ejmech.2009.04.025

  日期：2009.10

  To better use gossypol to find promising anticancer compounds, a series of new and known bis-Schiff base analogs of chiral gossypol were synthesized, and their anticancer activity on HeLa, U87 and M85 cells was tested. The results showed that through a simple chemical modification, less active (+)-gossypol could be converted into more active derivatives. When compared with (-)-gossypol, many more potent compounds that could be the promising anticancer agents were found, and some of them were more potent than the anticancer drug Cisplatin against all three cancer cell lines. By eliminating target functional groups, we observed that the major contributor to the anticancer activity of chiral gossypol seemed to be the phenolic groups, and not the aldehyde groups. Through comprehensive analysis of chiral gossypol analogs, the structure-activity relationships were elaborated. (C) 2009 Elsevier Masson SAS. All rights reserved.