3-(3-(phenylthio)furoxan-4-yloxy)propanol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(3-(phenylthio)furoxan-4-yloxy)propanol
• 英文别名: 3-[(5-Oxido-4-phenylsulfanyl-1,2,5-oxadiazol-5-ium-3-yl)oxy]propan-1-ol
• 化学式: C₁₁H₁₂N₂O₄S
• 分子量: 268.293
• InChiKey: AOGRJHPJLKYPKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-异丁基苯基)丙酰氯 、 3-(3-(phenylthio)furoxan-4-yloxy)propanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到3-[(5-Oxido-4-phenylsulfanyl-1,2,5-oxadiazol-5-ium-3-yl)oxy]propyl 2-[4-(2-methylpropyl)phenyl]propanoate
  参考文献：
  名称：

  A New Class of Ibuprofen Derivatives with Reduced Gastrotoxicity

  摘要：

  A new series of nonsteroidal and inflammatory drugs (NSAIDs) obtained by linking ibuprofen to selected furoxan moieties and to related furazans were synthesized and tested for their antiinflammatory, antiaggregatory, and ulcerogenic properties. All the derivatives are endowed with antiinflammatory activity comparable to that of ibuprofen, but, unlike this drug, they display reduced acute gastrotoxicity. The masking of the ibuprofen-free carboxylic group seems to be principally at the basis of this reduced topical irritant action. The two furoxan derivatives 8 and 9 also trigger potent antiaggregatory effects, principally as a consequence of their NO-donor ability.

  DOI：

  10.1021/jm0108799
• 作为产物：
  描述：

  potassium thiophenolate 、 3-苯磺酰基-4-(3-羟基丙氧基)-1,2,5-噁二唑-2-氧化物 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以45%的产率得到3-(3-(phenylthio)furoxan-4-yloxy)propanol
  参考文献：
  名称：

  A New Class of Ibuprofen Derivatives with Reduced Gastrotoxicity

  摘要：

  A new series of nonsteroidal and inflammatory drugs (NSAIDs) obtained by linking ibuprofen to selected furoxan moieties and to related furazans were synthesized and tested for their antiinflammatory, antiaggregatory, and ulcerogenic properties. All the derivatives are endowed with antiinflammatory activity comparable to that of ibuprofen, but, unlike this drug, they display reduced acute gastrotoxicity. The masking of the ibuprofen-free carboxylic group seems to be principally at the basis of this reduced topical irritant action. The two furoxan derivatives 8 and 9 also trigger potent antiaggregatory effects, principally as a consequence of their NO-donor ability.

  DOI：

  10.1021/jm0108799

文献信息

• A New Class of Ibuprofen Derivatives with Reduced Gastrotoxicity
  作者：Marco L. Lolli、Clara Cena、Claudio Medana、Loretta Lazzarato、Giuseppina Morini、Gabriella Coruzzi、Stefano Manarini、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm0108799

  日期：2001.10.1

  A new series of nonsteroidal and inflammatory drugs (NSAIDs) obtained by linking ibuprofen to selected furoxan moieties and to related furazans were synthesized and tested for their antiinflammatory, antiaggregatory, and ulcerogenic properties. All the derivatives are endowed with antiinflammatory activity comparable to that of ibuprofen, but, unlike this drug, they display reduced acute gastrotoxicity. The masking of the ibuprofen-free carboxylic group seems to be principally at the basis of this reduced topical irritant action. The two furoxan derivatives 8 and 9 also trigger potent antiaggregatory effects, principally as a consequence of their NO-donor ability.