3-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]propan-1-ol | 906096-83-1

• 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-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]propan-1-ol
• 英文别名: 3-[4-(Benzenesulfonyl)-1,2,5-oxadiazol-3-yl]propan-1-ol
• CAS: 906096-83-1
• 化学式: C₁₁H₁₂N₂O₄S
• 分子量: 268.293
• InChiKey: HNHAFWYPPNQEHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]propan-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 tert-butyl {3-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]propyl}carbamate
  参考文献：
  名称：

  羟基1,2,5-恶二唑基部分是羧基的生物等排体。γ-氨基丁酸（GABA）相关化合物的合成，电离常数和药理学表征。

  摘要：

  合成了三个含有氨基烷基取代基的4-取代的1,2,5-恶二唑-3-醇（γ-氨基丁酸（GABA）的类似物和同系物），以研究羟基1,2,5-恶二唑基部分是GABA受体上的羧基。目标化合物的pK（a）值接近GABA。在培养的大脑皮层神经元的GABA（A）受体上，鉴定出弱激动剂和部分激动剂谱，表明4-羟基-1,2,5-恶二唑-3-基单元是非经典的羧基生物等排体。

  DOI：

  10.1021/jm051288b
• 作为产物：
  描述：

  、 3,4-bis-(phenylsulfonyl)furazan 以 四氢呋喃 为溶剂， 以88%的产率得到3-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]propan-1-ol
  参考文献：
  名称：

  羟基1,2,5-恶二唑基部分是羧基的生物等排体。γ-氨基丁酸（GABA）相关化合物的合成，电离常数和药理学表征。

  摘要：

  合成了三个含有氨基烷基取代基的4-取代的1,2,5-恶二唑-3-醇（γ-氨基丁酸（GABA）的类似物和同系物），以研究羟基1,2,5-恶二唑基部分是GABA受体上的羧基。目标化合物的pK（a）值接近GABA。在培养的大脑皮层神经元的GABA（A）受体上，鉴定出弱激动剂和部分激动剂谱，表明4-羟基-1,2,5-恶二唑-3-基单元是非经典的羧基生物等排体。

  DOI：

  10.1021/jm051288b

文献信息

• 4-Hydroxy-1,2,5-oxadiazol-3-yl Moiety as Bioisoster of the Carboxy Function. Synthesis, Ionization Constants, and Molecular Pharmacological Characterization at Ionotropic Glutamate Receptors of Compounds Related to Glutamate and Its Homologues
  作者：Marco L. Lolli、Cecilia Giordano、Darryl S. Pickering、Barbara Rolando、Kasper B. Hansen、Antonio Foti、Alberto Contreras-Sanz、Ahmad Amir、Roberta Fruttero、Alberto Gasco、Birgitte Nielsen、Tommy N. Johansen

  DOI：10.1021/jm1001452

  日期：2010.5.27

  In order to investigate the 4-hydroxy-1,2,5-oxadiazol-3-yl moiety as a carboxylic acid bioisoster at ionotropic glutamate receptors (iGluRs), a series of acidic alpha-aminocarboxylic acids in which the distal carboxy group was replaced by the 4-hydroxy-1,2,5-oxadiazol-3-yl group was synthesized. Ionization constants were determined. All target compounds, except the Asp analogue 12, were resolved using chiral HPLC. Whereas 12 showed good affinity exclusively at NMDA receptors, the Glu analogue, (+)-10, was an unselective, though potent AMPA receptor preferring agonist (EC(50) = 10 mu M at iGluR2) showing only low stereoselectivity. The two higher Glu homologues, (+)-15 and (+)-18, turned out to be weak agonists at iGluR2 as well as weak antagonists at NR1/NR2A, whereas the corresponding (-)-isomers were selective NR1/NR2A antagonists with somewhat higher potency. The results proved the 4-hydroxy-1,2,5-oxadiazol-3-yl moiety to be a useful bioisoster at all three classes of iGluRs, capable of being integrated into agonists as well as antagonists.
• Hydroxy-1,2,5-oxadiazolyl Moiety as Bioisoster of the Carboxy Function. Synthesis, Ionization Constants, and Pharmacological Characterization of γ-Aminobutyric Acid (GABA) Related Compounds
  作者：Marco L. Lolli、Suzanne L. Hansen、Barbara Rolando、Birgitte Nielsen、Petrine Wellendorph、Karsten Madsen、Orla Miller Larsen、Uffe Kristiansen、Roberta Fruttero、Alberto Gasco、Tommy N. Johansen

  DOI：10.1021/jm051288b

  日期：2006.7.1

  Three 4-substituted 1,2,5-oxadiazol-3-ols containing aminoalkyl substituents (analogues and homologues of gamma-aminobutyric acid (GABA)) were synthesized to investigate the hydroxy-1,2,5-oxadiazolyl moiety as a bioisoster for a carboxyl group at GABA receptors. The pK(a) values of the target compounds were close to those of GABA. At GABA(A) receptors of cultured cerebral cortical neurons, weak agonist

  合成了三个含有氨基烷基取代基的4-取代的1,2,5-恶二唑-3-醇（γ-氨基丁酸（GABA）的类似物和同系物），以研究羟基1,2,5-恶二唑基部分是GABA受体上的羧基。目标化合物的pK（a）值接近GABA。在培养的大脑皮层神经元的GABA（A）受体上，鉴定出弱激动剂和部分激动剂谱，表明4-羟基-1,2,5-恶二唑-3-基单元是非经典的羧基生物等排体。