(4-oxo-4,5-dihydro-[1,2,5]oxadiazol-3-yl)-acetic acid | 3201-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4-oxo-4,5-dihydro-[1,2,5]oxadiazol-3-yl)-acetic acid
• 英文别名: (4-Oxo-4,5-dihydro-[1,2,5]oxadiazol-3-yl)-essigsaeure；(4-oxo-4,5-dihydro-1,2,5-oxadiazol-3-yl)acetic acid；2-(4-oxo-1,2,5-oxadiazol-3-yl)acetic Acid
• CAS: 3201-54-5
• 化学式: C₄H₄N₂O₄
• mdl: MFCD00955574
• 分子量: 144.087
• InChiKey: PSTJTBFRVAIJNV-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C
• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (4-oxo-4,5-dihydro-[1,2,5]oxadiazol-3-yl)-acetic acid 以 乙醚 为溶剂， 生成 methyl 2-(4-methoxy-1,2,5-oxadiazol-3-yl)acetate
  参考文献：
  名称：

  The tautomerism of heteroaromatic compounds with five-membered rings—VIII

  摘要：

  DOI：

  10.1016/s0040-4020(01)98638-7
• 作为产物：
  描述：

  sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate 在 sodium hydroxide 、 羟胺 作用下， 生成 (4-oxo-4,5-dihydro-[1,2,5]oxadiazol-3-yl)-acetic acid
  参考文献：
  名称：

  The tautomerism of heteroaromatic compounds with five-membered rings—VIII

  摘要：

  DOI：

  10.1016/s0040-4020(01)98638-7

文献信息

• [EN] NOVEL M3 MUSCARINIC ACETYLCHOLINE RECEPTOR ANTAGONISTS<br/>[FR] NOUVEAUX ANTAGONISTES DU RECEPTEUR DE L'ACETYLCHOLINE MUSCARINIQUE M3
  申请人：GLAXO GROUP LTD

  公开号：WO2005087236A1

  公开（公告）日：2005-09-22

  Muscarinic Acetylcholine receptor antagonists and methods of using them are provided.

  提供了肌氢酸乙酰胆碱受体拮抗剂及其使用方法。
• [EN] SUBSTITUTED N-HYDROXYAMIDINOHETEROCYCLES AS MODULATORS OF INDOLEAMINE 2,3- DIOXYGENASE<br/>[FR] N-HYDROXYAMIDINOHÉTÉROCYCLES SUBSTITUÉS EN TANT QUE MODULATEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE
  申请人：PHENEX DISCOVERY VERWALTUNGS GMBH

  公开号：WO2018083241A1

  公开（公告）日：2018-05-11

  The invention provides modulators of indoleamine 2,3-dioxygenase (IDO1) and their use in the prophylaxis and/or treatment of IDO1-mediated diseases. Specifically, the present invention provides compounds according to Formula (I) an enantiomer, diastereomer, tautomer or pharmaceutically acceptable salt thereof.

  本发明提供了吲哚胺2,3-双加氧酶（IDO1）的调节剂及其在预防或治疗IDO1介导的疾病中的用途。具体而言，本发明提供的是符合公式（I）的化合物、其对应的手性异构体、对映异构体、互变异构体或药用可接受的盐。
• 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.
• Hantzsch; Urbahn, Chemische Berichte, 1895, vol. 28, p. 760
  作者：Hantzsch、Urbahn

  DOI：——

  日期：——
• The tautomerism of heteroaromatic compounds with five-membered rings—VIII
  作者：A.R. Katritzky、B. Wallis、R.T.C. Brownlee、R.D. Topsom

  DOI：10.1016/s0040-4020(01)98638-7

  日期：1965.1