3-[(3-phenylsulfonyl)furoxan-4-yloxy]propan-1-ol | 373369-11-0

• 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: 3-[(3-phenylsulfonyl)furoxan-4-yloxy]propan-1-ol
• 英文别名: 3-(4-(benzenesulfonyl)furazan-3-yloxy)propanol；4-(3-Hydroxypropoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole；3-[[4-(benzenesulfonyl)-1,2,5-oxadiazol-3-yl]oxy]propan-1-ol
• CAS: 373369-11-0
• 化学式: C₁₁H₁₂N₂O₅S
• 分子量: 284.293
• InChiKey: HVSZXZWHPNQHIG-UHFFFAOYSA-N

物化性质

• 沸点：
  512.8±60.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(3-phenylsulfonyl)furoxan-4-yloxy]propan-1-ol 在 吡啶 、 Jones reagent 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 11.0h， 生成 2-[(3-{[(4-phenylsulfonyl)furazan-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-bis-(phenylsulfonyl)furazan 、 1,3-丙二醇 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到3-[(3-phenylsulfonyl)furoxan-4-yloxy]propan-1-ol
  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

• Antiinflammatory, Gastrosparing, and Antiplatelet Properties of New NO-Donor Esters of Aspirin
  作者：Clara Cena、Marco L. Lolli、Loretta Lazzarato、Elena Guaita、Giuseppina Morini、Gabriella Coruzzi、Stuart P. McElroy、Ian L. Megson、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm020969t

  日期：2003.2.1

  aspirin is joined by an ester linkage to furoxan moieties, with different ability to release NO, were synthesized and tested for NO-releasing, antiinflammatory, antiaggregatory, and ulcerogenic properties. Related furazan derivatives, aspirin, its propyl ester, and its gamma-nitrooxypropyl ester were taken as references. All the products described present an antiinflammatory trend, maximized in derivatives

  合成了一系列新的非甾体抗炎药，其中阿司匹林通过酯键连接到具有不同释放NO能力的呋喃喃部分上，并测试了其释放NO，抗炎，抗聚集和致溃疡的特性。相关的呋喃山衍生物，阿司匹林，其丙基酯和其γ-硝基氧丙基酯均作为参考。所描述的所有产品均表现出抗炎趋势，在衍生物12、16和17中达到最大，主要由于其酯类性质，它们没有急性胃毒性，并且显示出主要由其释放NO的能力决定的抗血小板活性。它们在人血清中不具有阿司匹林前药的作用。
• Design, synthesis, and biological characterization of potential antiatherogenic nitric oxide releasing tocopherol analogs
  作者：Gloria V. López、Carlos Batthyány、Fabiana Blanco、Horacio Botti、Andrés Trostchansky、Eduardo Migliaro、Rafael Radi、Mercedes González、Hugo Cerecetto、Homero Rubbo

  DOI：10.1016/j.bmc.2005.05.060

  日期：2005.10

  Synthesis and biological characterization of a series of alpha-tocopherol analogs with NO-releasing capacity are reported. The selected NO-donor moieties were nitrooxy and furoxan. All products were tested for their in vitro NO-releasing capacities, vasodilating properties, and antiplatelet activity. They were also capable of preventing LDL oxidation. (c) 2005 Elsevier Ltd. All rights reserved.
• Nitric Oxide Donor Doxorubicins Accumulate into Doxorubicin-Resistant Human Colon Cancer Cells Inducing Cytotoxicity
  作者：Konstantin Chegaev、Chiara Riganti、Loretta Lazzarato、Barbara Rolando、Stefano Guglielmo、Ivana Campia、Roberta Fruttero、Amalia Bosia、Alberto Gasco

  DOI：10.1021/ml100302t

  日期：2011.7.14

  Products 4 and 5, obtained by conjugation of doxorubicin with nitric oxide (NO) donor nitrooxy and phenylsulfonyl furoxan moieties, respectively, accumulate in doxorubicin-resistant human colon cancer cells (HT29-dx), inducing high cytotoxicity. This behavior parallels the ability of the compounds to generate NO, detected as nitrite, in these cells. Preliminary immunoblotting studies suggest that the mechanism that underlies the cytotoxic effect could involve inhibition of cellular drug efflux due to nitration of tyrosine residues of the MRP3 protein pump.