4-((1-hydroxypropan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide | 930117-23-0

• 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-((1-hydroxypropan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
• CAS: 930117-23-0
• 化学式: C₁₁H₁₂N₂O₆S
• 分子量: 300.292
• InChiKey: MOYGNQFKHXYQJR-UHFFFAOYSA-N

物化性质

• 沸点：
  554.1±60.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116.57
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-((1-hydroxypropan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  Synthesis and Bioactivity of Furoxan-Based Nitric Oxide-Releasing Colchicine Derivatives as Anticancer Agents

  摘要：

  通过将呋喃并[1,2-a]唑酮与N-甲基秋水仙酰胺通过适当的间隔臂偶联，合成了一系列新的NO供体型秋水仙碱衍生物（9a-j），并采用MTT法评估了它们对四种人癌细胞系的体外细胞毒性。结果发现，许多衍生物表现出显著的活性，特别是化合物9f的细胞毒性活性显著强于秋水仙碱。

  DOI：

  10.14233/ajchem.2013.13635
• 作为产物：
  描述：

  1,2-丙二醇 、 呋咱氮氧化物供体 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-((1-hydroxypropan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Synthesis and Bioactivity of Furoxan-Based Nitric Oxide-Releasing Colchicine Derivatives as Anticancer Agents

  摘要：

  通过将呋喃并[1,2-a]唑酮与N-甲基秋水仙酰胺通过适当的间隔臂偶联，合成了一系列新的NO供体型秋水仙碱衍生物（9a-j），并采用MTT法评估了它们对四种人癌细胞系的体外细胞毒性。结果发现，许多衍生物表现出显著的活性，特别是化合物9f的细胞毒性活性显著强于秋水仙碱。

  DOI：

  10.14233/ajchem.2013.13635

文献信息

• Synthesis and Biological Study of 3-Butyl-1-(2,6-dichlorophenyl)-1H-[1,2,4]triazol- 5(4H)-one Derivatives as Anti-hypertension Drugs
  作者：Yanchun Zhang、Jinpei Zhou、Weihong Pan、Xiaoming Wu、Shuai Wang

  DOI：10.2174/157018010789869370

  日期：2010.1.1

  A series of nitric oxide-donating derivatives of [1,2,4]triazol-5(4H)-one (9a-f and 15a-f) as a novel class of angiotensin II receptor AT1 antagonists have been designed and synthesized by coupling furoxan and nitric oxide with lead compound 1. The synthesized compounds were evaluated for their antagonism of AT1 receptor with induced contraction in the rabbit thoracic aortic ring and the results showed that compounds 9b, 15b and 15d exhibited potent antagonistic activity of AT1 receptor. Moreover 9b, 15b, 15d, 15e had good maximum NO release amount of this series.

  一系列新型血管紧张素II受体AT1拮抗剂——[1,2,4]三唑-5(4H)-酮（9a-f和15a-f）的硝酸氧化物衍生物，通过将呋喃并氧和硝酸氧化物与前导化合物1结合而设计并合成。合成的化合物在兔胸主动脉环中诱导收缩的情况下，对其AT1受体的拮抗作用进行了评估，结果显示化合物9b、15b和15d展现出强大的AT1受体拮抗活性。此外，9b、15b、15d、15e在这一系列化合物中具有良好的最大NO释放量。
• Design, synthesis and biological evaluation of novel furoxan-based coumarin derivatives as antitumor agents
  作者：Zhuo Zhang、Zhi-Wei Bai、Yong Ling、Li-Qin He、Peng Huang、Hong-Xia Gu、Rong-Feng Hu

  DOI：10.1007/s00044-018-2140-x

  日期：2018.4

  In order to find new anticancer drugs, a series of novel furoxan-based coumarin derivatives (10a-k) were synthesized and evaluated for their antiproliferative activities in vitro. All compounds displayed more potent inhibition on human cervical cancer HeLa cell proliferation than coumarin-3-carboxylic acid, and compounds 10b, 10c, 10f, 10h, and 10i with IC50 values ranging from 0.88 to 5.95 mu M were even stronger than doxorubicin (IC50 = 10.21 mu M). The further study showed that compound 10i exerted the highest antiproliferative activity (IC50 = 0.60 mu M) against human breast cancer MCF-7 cells, and compound 10f had broader spectrum antiproliferative activity against five cancer cells with IC50 values in the low micromolar range of 1.86-9.85 mu M. More interestingly, compound 10f had little effect on normal intestinal epithelial CCD841 cells. Our findings suggest that these novel furoxan-based coumarin derivatives may provide a new framework for the discovery of novel antitumor agents for the intervention of human carcinoma cells.