4-(2-(2-hydroxyethylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide | 1170668-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-(2-hydroxyethylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide
• 英文别名: 2-[2-[[4-(Benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]ethylamino]ethanol
• CAS: 1170668-02-6
• 化学式: C₁₂H₁₅N₃O₆S
• 分子量: 329.334
• InChiKey: GNWXBWLBSGZLIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(2-(2-hydroxyethylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide 、 2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)-benzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以420 mg的产率得到4-(2-(N-(2-hydroxyethyl)-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)benzamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide
  参考文献：
  名称：

  Novel Nitric Oxide-Releasing Derivatives of Farnesylthiosalicylic Acid: Synthesis and Evaluation of Antihepatocellular Carcinoma Activity

  摘要：

  Novel furoxan-based nitric oxide (NO) releasing derivatives (8a-p) of farnesylthiosalicylic acid (FTS) were synthesized. Compound 8l displayed the strongest inhibition on the proliferation of human hepatocellular carcinoma (HCC) cells in vitro, superior to FTS, sorafenib, and furoxan moiety, selectively induced high frequency of HCC cell apoptosis, and produced high levels of NO in HCC cells but not in nontumor liver cells. Furthermore, 8l exhibited low acute toxicity to mice and significantly inhibited the growth of HCC tumors in vivo and the Ras-related signaling in the tumors. Therefore, our novel findings may provide a new framework for the design of new NO-releasing furoxan/FTS hybrids for the intervention of human HCC.

  DOI：

  10.1021/jm1014814
• 作为产物：
  描述：

  呋咱氮氧化物供体 、 二乙醇胺 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以65%的产率得到4-(2-(2-hydroxyethylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide
  参考文献：
  名称：

  Novel Nitric Oxide-Releasing Derivatives of Farnesylthiosalicylic Acid: Synthesis and Evaluation of Antihepatocellular Carcinoma Activity

  摘要：

  Novel furoxan-based nitric oxide (NO) releasing derivatives (8a-p) of farnesylthiosalicylic acid (FTS) were synthesized. Compound 8l displayed the strongest inhibition on the proliferation of human hepatocellular carcinoma (HCC) cells in vitro, superior to FTS, sorafenib, and furoxan moiety, selectively induced high frequency of HCC cell apoptosis, and produced high levels of NO in HCC cells but not in nontumor liver cells. Furthermore, 8l exhibited low acute toxicity to mice and significantly inhibited the growth of HCC tumors in vivo and the Ras-related signaling in the tumors. Therefore, our novel findings may provide a new framework for the design of new NO-releasing furoxan/FTS hybrids for the intervention of human HCC.

  DOI：

  10.1021/jm1014814

文献信息

• Novel Nitric Oxide-Releasing Derivatives of Farnesylthiosalicylic Acid: Synthesis and Evaluation of Antihepatocellular Carcinoma Activity
  作者：Yong Ling、Xiaolei Ye、Zhenzhen Zhang、Yihua Zhang、Yisheng Lai、Hui Ji、Sixun Peng、Jide Tian

  DOI：10.1021/jm1014814

  日期：2011.5.12

  Novel furoxan-based nitric oxide (NO) releasing derivatives (8a-p) of farnesylthiosalicylic acid (FTS) were synthesized. Compound 8l displayed the strongest inhibition on the proliferation of human hepatocellular carcinoma (HCC) cells in vitro, superior to FTS, sorafenib, and furoxan moiety, selectively induced high frequency of HCC cell apoptosis, and produced high levels of NO in HCC cells but not in nontumor liver cells. Furthermore, 8l exhibited low acute toxicity to mice and significantly inhibited the growth of HCC tumors in vivo and the Ras-related signaling in the tumors. Therefore, our novel findings may provide a new framework for the design of new NO-releasing furoxan/FTS hybrids for the intervention of human HCC.