ethyl 2-(3-(p-tolyl)-1,2,4-oxadiazol-5-yl)acetate | 56935-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(3-(p-tolyl)-1,2,4-oxadiazol-5-yl)acetate
• 英文别名: (3-p-tolyl-[1,2,4]oxadiazol-5-yl)-acetic acid ethyl ester；(3-p-Tolyl-[1,2,4]oxadiazol-5-yl)-acetic acid ethyl ester；ethyl 2-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]acetate
• CAS: 56935-59-2
• 化学式: C₁₃H₁₄N₂O₃
• mdl: MFCD18088246
• 分子量: 246.266
• InChiKey: FMTSSLAFVSMTJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-(p-tolyl)-1,2,4-oxadiazol-5-yl)acetate 在 氢氧化钾 作用下， 生成 3-<(Acetyloxy)methyl>-7-<1,2,4-oxadiazol-5-yl-acetyl>-amino-3-cephem-4-carbon-saeure
  参考文献：
  名称：

  Malabarba; Cavalleri; Berti, Farmaco, Edizione Scientifica, 1977, vol. 32, # 9, p. 650 - 664

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲酰乙酸乙酯 、 4-甲基苯甲酰胺肟 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 1.0h， 以75%的产率得到ethyl 2-(3-(p-tolyl)-1,2,4-oxadiazol-5-yl)acetate
  参考文献：
  名称：

  Acetic Acid Aldose Reductase Inhibitors Bearing a Five-Membered Heterocyclic Core with Potent Topical Activity in a Visual Impairment Rat Model

  摘要：

  A number of 1,2,4-oxadiazol-5-yl-acetic acids and oxazol-4-yl-acetic acids were synthesized and tested for their ability to inhibit aldose reductase (ALR2). The oxadiazole derivatives, 7c, 7f, 7i, and 8h, 8i, proved to be the most active compounds, exhibiting inhibitory levels in the submicromolar range. In this series, the phenyl group turned out to be the preferred substitution pattern, as its lengthening to a benzyl moiety determined a general reduction of the inhibitory potency. The lead compound, 2-[3-(4-methoxyphenyl)1,2,4-oxadiazol-5-yl] acetic acid, 7c, showed an excellent in vivo activity, proving to prevent cataract development in severely galactosemic rats when administered as an eye-drop solution in the precorneal region of the animals. Computational studies on the ALR2 inhibitors were performed to rationalize the structure-activity relationships observed and to provide the basis for further structure-guided design of novel ALR2 inhibitors.

  DOI：

  10.1021/jm701613h

文献信息

• Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: synthesis of fully substituted pyrimidines
  作者：Ekaterina E. Galenko、Timur O. Zanakhov、Mikhail S. Novikov、Alexander F. Khlebnikov

  DOI：10.1039/d3ob00148b

  日期：——

  6-dihydropyrimidine-5-carboxylates can be easily prepared by a metal carbonyl mediated rearrangement of ethyl 3-oxo-2-(1,2,4-oxadiazol-5-yl)propanoates. The irradiation of a mixture of oxadiazoles and Fe(CO)5 in wet solvents with a 365 nm LED at room temperature for 2 h followed by heating at 80 °C for 2 h gives pyrimidines in up to 90% yield. This procedure enables the preparation of 6-oxo-1,6-dihydrop

  通过金属羰基介导的 3-氧代-2-(1,2,4-恶二唑-5-基) 丙酸乙酯的重排，可以很容易地制备各种取代的 6-氧代-1,6-二氢嘧啶-5-羧酸乙酯。在室温下用 365 nm LED 照射湿溶剂中恶二唑和Fe(CO) 5的混合物2 小时，然后在 80 °C 下加热 2 小时，得到高达 90% 产率的嘧啶。该程序能够制备 6-oxo-1,6-dihydropyrimidine-5-carboxylates，在 C2 位置具有各种芳基取代基，在 C4 位置具有烷基或芳基取代基。1-(1,2,4-Oxadiazol-5-yl)propan-2-ones 类似地得到 6-methylpyrimidin-4(3 H)-ones，尽管产量较低。Ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates 可以很容易地在 C6 位置通过溴化修饰，然后进行交叉偶联反应，得到带有吡啶基、氨基和乙炔基取代基的
• Acetic Acid Aldose Reductase Inhibitors Bearing a Five-Membered Heterocyclic Core with Potent Topical Activity in a Visual Impairment Rat Model
  作者：Concettina La Motta、Stefania Sartini、Silvia Salerno、Francesca Simorini、Sabrina Taliani、Anna Maria Marini、Federico Da Settimo、Luciana Marinelli、Vittorio Limongelli、Ettore Novellino

  DOI：10.1021/jm701613h

  日期：2008.6.1

  A number of 1,2,4-oxadiazol-5-yl-acetic acids and oxazol-4-yl-acetic acids were synthesized and tested for their ability to inhibit aldose reductase (ALR2). The oxadiazole derivatives, 7c, 7f, 7i, and 8h, 8i, proved to be the most active compounds, exhibiting inhibitory levels in the submicromolar range. In this series, the phenyl group turned out to be the preferred substitution pattern, as its lengthening to a benzyl moiety determined a general reduction of the inhibitory potency. The lead compound, 2-[3-(4-methoxyphenyl)1,2,4-oxadiazol-5-yl] acetic acid, 7c, showed an excellent in vivo activity, proving to prevent cataract development in severely galactosemic rats when administered as an eye-drop solution in the precorneal region of the animals. Computational studies on the ALR2 inhibitors were performed to rationalize the structure-activity relationships observed and to provide the basis for further structure-guided design of novel ALR2 inhibitors.
• Malabarba; Cavalleri; Berti, Farmaco, Edizione Scientifica, 1977, vol. 32, # 9, p. 650 - 664
  作者：Malabarba、Cavalleri、Berti、Arioli

  DOI：——

  日期：——