N-[acetyl-3-(3-phenylsulfonyl-1,2,5-oxadiazol-4-oxy)-propylester]-isosteviol-amide | 1606163-14-7

• 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-[acetyl-3-(3-phenylsulfonyl-1,2,5-oxadiazol-4-oxy)-propylester]-isosteviol-amide
• 英文别名: 3-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]propyl 2-[[(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carbonyl]amino]acetate
• CAS: 1606163-14-7
• 化学式: C₃₃H₄₃N₃O₉S
• 分子量: 657.785
• InChiKey: XZUCNBMTQVDXCO-SXHOGQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  异甜菊醇 在 4-二甲氨基吡啶 、 氯化亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 N-[acetyl-3-(3-phenylsulfonyl-1,2,5-oxadiazol-4-oxy)-propylester]-isosteviol-amide
  参考文献：
  名称：

  Synthesis and cytotoxic activity of nitric oxide-releasing isosteviol derivatives

  摘要：

  Fifteen novel hybrids containing diterpene skeleton and nitric oxide (NO) donor were prepared from isosteviol. All the compounds were tested on preliminary cytotoxicity, and the results showed that six target compounds (8c, 10b, 14a, 14c, 18c, and 18d) exhibited anti-proliferation activity on HepG2 cells, with 8c (IC50 = 4.24 mu M) and 18d (IC50 = 2.75 mu M) superior to the positive control CDDO-Me (2-cyano-3,12-dioxo-oleana-1,9(11)-dien-28-acid methyl ester, IC50 = 4.99 mu M); eleven target compounds(8a-c, 9a-c, 10a-b, 14a, 14c, 18d) exhibited anti-proliferation activities on B16F10 cells at different levels, among them, seven compounds were more potent than comptothecin (IC50 = 2.78 mu M) and CDDO-Me (IC50 = 5.85 mu M), particularly, 10b (IC50 = 0.02 mu M) presented the strongest effect, which was selected as a candidate for further study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.004

文献信息

• Synthesis and cytotoxic activity of nitric oxide-releasing isosteviol derivatives
  作者：Ting-ting Wang、Yan Liu、Li Chen

  DOI：10.1016/j.bmcl.2014.03.004

  日期：2014.5

  Fifteen novel hybrids containing diterpene skeleton and nitric oxide (NO) donor were prepared from isosteviol. All the compounds were tested on preliminary cytotoxicity, and the results showed that six target compounds (8c, 10b, 14a, 14c, 18c, and 18d) exhibited anti-proliferation activity on HepG2 cells, with 8c (IC50 = 4.24 mu M) and 18d (IC50 = 2.75 mu M) superior to the positive control CDDO-Me (2-cyano-3,12-dioxo-oleana-1,9(11)-dien-28-acid methyl ester, IC50 = 4.99 mu M); eleven target compounds(8a-c, 9a-c, 10a-b, 14a, 14c, 18d) exhibited anti-proliferation activities on B16F10 cells at different levels, among them, seven compounds were more potent than comptothecin (IC50 = 2.78 mu M) and CDDO-Me (IC50 = 5.85 mu M), particularly, 10b (IC50 = 0.02 mu M) presented the strongest effect, which was selected as a candidate for further study. (C) 2014 Elsevier Ltd. All rights reserved.