N,N'-(oxybis(ethane-2,1-diyl))bis(2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide) | 1531591-34-0

• 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: N,N'-(oxybis(ethane-2,1-diyl))bis(2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide)
• 英文别名: 2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanyl-N-[2-[2-[[2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylbenzoyl]amino]ethoxy]ethyl]benzamide
• CAS: 1531591-34-0
• 化学式: C₄₈H₆₈N₂O₃S₂
• 分子量: 785.212
• InChiKey: CWYUWBPGECXRDQ-JLFQPTCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  55
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反,反-法呢基溴 在 草酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.5h， 生成 N-(2-(2-aminoethoxy)ethyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide 、 N,N'-(oxybis(ethane-2,1-diyl))bis(2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide)
  参考文献：
  名称：

  Synthesis and biological evaluation of farnesylthiosalicylamides as potential anti-tumor agents

  摘要：

  Fourteen hybrids of farnesylthiosalicylic acid (FTS) with various diamines were synthesized and biologically evaluated. It was found that FTS-monoamide molecules (10a-g) displayed strong anti-proliferative activity against seven human cancer cell lines, superior to FTS and FTS-bisamide compounds (11a-g). The mono-amide 10f was the most active, with IC(50)s of 3.78-7.63 mu M against all tested cancer cells, even more potent than sorafenib (9.12-22.9 mu M). In addition, 10f induced SMMC-7721 cell apoptosis, down-regulated the expression of Bcl-2 and up-regulated Bax and caspase-3. Furthermore, 10f had the improved aqueous solubility relative to FTS. Finally, treatment with 10f dose-dependently inhibited the Ras-related signaling pathways in SMMC-7721 cells. Collectively, 10f could be a promising candidate for the intervention of human cancers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.013

文献信息

• Synthesis and biological evaluation of farnesylthiosalicylamides as potential anti-tumor agents
  作者：Yong Ling、Zhiqiang Wang、Hongyan Zhu、Xuemin Wang、Wei Zhang、Xinyang Wang、Li Chen、Zhangjian Huang、Yihua Zhang

  DOI：10.1016/j.bmc.2013.11.013

  日期：2014.1

  Fourteen hybrids of farnesylthiosalicylic acid (FTS) with various diamines were synthesized and biologically evaluated. It was found that FTS-monoamide molecules (10a-g) displayed strong anti-proliferative activity against seven human cancer cell lines, superior to FTS and FTS-bisamide compounds (11a-g). The mono-amide 10f was the most active, with IC(50)s of 3.78-7.63 mu M against all tested cancer cells, even more potent than sorafenib (9.12-22.9 mu M). In addition, 10f induced SMMC-7721 cell apoptosis, down-regulated the expression of Bcl-2 and up-regulated Bax and caspase-3. Furthermore, 10f had the improved aqueous solubility relative to FTS. Finally, treatment with 10f dose-dependently inhibited the Ras-related signaling pathways in SMMC-7721 cells. Collectively, 10f could be a promising candidate for the intervention of human cancers. (C) 2013 Elsevier Ltd. All rights reserved.