3-(4-phenylfurazan-3-yloxy)propanoic acid | 1339138-42-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-phenylfurazan-3-yloxy)propanoic acid
• 英文别名: 3-[(4-Phenyl-1,2,5-oxadiazol-3-yl)oxy]propanoic acid
• CAS: 1339138-42-9
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: XHUXRRXEEYZHJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-phenylfurazan-3-yloxy)propanoic acid 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2-({3-[(4-phenylfurazan-3-yl)oxy]propanoyl}oxy)benzoic acid
  参考文献：
  名称：

  Searching for new NO-donor aspirin-like molecules: Furoxanylacyl derivatives of salicylic acid and related furazans

  摘要：

  A new group of derivatives of salicylic acid containing NO-donor furoxans, and the related des-NO-furazans, were synthesized and evaluated as new aspirin-like molecules. Their stability was assessed in acid (pH 1) and physiological solutions (pH 7.4), and in human serum. No compound exhibited COX-inhibitory activity against COX-1 and COX-2 isoforms, when tested up to 100 mu M, respectively, on isolated platelets and on monocytes. Phenylsulfonyl- and cyano-substituted furoxans inhibited platelet aggregation induced by collagen in human platelet-rich plasma, through a cGMP dependent mechanism. Furoxan derivatives displayed cGMP-dependent vasodilator activities, tested on rat aorta strips precontracted with phenylephrine. All products showed anti-inflammatory activity similar to that of ASA, tested on rats by the carrageenan-induced paw edema assay. Unlike ASA, all products showed markedly reduced gastrotoxicity in a rat lesion model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.018
• 作为产物：
  描述：

  3-(4-phenylfurazan-3-yloxy)propanol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以71%的产率得到3-(4-phenylfurazan-3-yloxy)propanoic acid
  参考文献：
  名称：

  Searching for new NO-donor aspirin-like molecules: Furoxanylacyl derivatives of salicylic acid and related furazans

  摘要：

  A new group of derivatives of salicylic acid containing NO-donor furoxans, and the related des-NO-furazans, were synthesized and evaluated as new aspirin-like molecules. Their stability was assessed in acid (pH 1) and physiological solutions (pH 7.4), and in human serum. No compound exhibited COX-inhibitory activity against COX-1 and COX-2 isoforms, when tested up to 100 mu M, respectively, on isolated platelets and on monocytes. Phenylsulfonyl- and cyano-substituted furoxans inhibited platelet aggregation induced by collagen in human platelet-rich plasma, through a cGMP dependent mechanism. Furoxan derivatives displayed cGMP-dependent vasodilator activities, tested on rat aorta strips precontracted with phenylephrine. All products showed anti-inflammatory activity similar to that of ASA, tested on rats by the carrageenan-induced paw edema assay. Unlike ASA, all products showed markedly reduced gastrotoxicity in a rat lesion model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.018

文献信息

• Searching for new NO-donor aspirin-like molecules: Furoxanylacyl derivatives of salicylic acid and related furazans
  作者：Loretta Lazzarato、Clara Cena、Barbara Rolando、Elisabetta Marini、Marco Lucio Lolli、Stefano Guglielmo、Elena Guaita、Giuseppina Morini、Gabriella Coruzzi、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.bmc.2011.08.018

  日期：2011.10

  A new group of derivatives of salicylic acid containing NO-donor furoxans, and the related des-NO-furazans, were synthesized and evaluated as new aspirin-like molecules. Their stability was assessed in acid (pH 1) and physiological solutions (pH 7.4), and in human serum. No compound exhibited COX-inhibitory activity against COX-1 and COX-2 isoforms, when tested up to 100 mu M, respectively, on isolated platelets and on monocytes. Phenylsulfonyl- and cyano-substituted furoxans inhibited platelet aggregation induced by collagen in human platelet-rich plasma, through a cGMP dependent mechanism. Furoxan derivatives displayed cGMP-dependent vasodilator activities, tested on rat aorta strips precontracted with phenylephrine. All products showed anti-inflammatory activity similar to that of ASA, tested on rats by the carrageenan-induced paw edema assay. Unlike ASA, all products showed markedly reduced gastrotoxicity in a rat lesion model. (C) 2011 Elsevier Ltd. All rights reserved.