(2-p-Tolyl-oxazol-4-yl)-acetic acid ethyl ester | 84446-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-p-Tolyl-oxazol-4-yl)-acetic acid ethyl ester
• 英文别名: Ethyl 2-[2-(4-methylphenyl)-1,3-oxazol-4-yl]acetate
• CAS: 84446-04-8
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: IWCUQNDXZQBCLS-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C(Solv: ligroine (8032-32-4))
• 沸点：
  160 °C(Press: 7 Torr)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-p-Tolyl-oxazol-4-yl)-acetic acid ethyl ester 在 sodium hydroxide 、 水 作用下， 反应 1.0h， 以54%的产率得到2-[2-(4-Methylphenyl)-1,3-oxazol-4-yl]acetic acid
  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
• 作为产物：
  描述：

  (Z)-5-ethoxycarbonylmethylene-5,6-dihydro-3-p-methylphenyl-4H-1,2,4-oxadiazine 以6%的产率得到
  参考文献：
  名称：

  TABEI, KATSUMI;KAWASHIMA, ETSUKO;TAKADA, TOYOZO;KATO, TETSUZO, HETEROCYCLES, 1982, 19, N 11, 2061-2066

  摘要：

  DOI：

文献信息

• Tabei, Katsumi; Kawashima, Etsuko; Takada, Toyozo, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 569 - 574
  作者：Tabei, Katsumi、Kawashima, Etsuko、Takada, Toyozo、Kato, Tetsuzo

  DOI：——

  日期：——
• Tabei, Katsumi; Kawashima, Etsuko; Takada, Toyozo, Heterocycles, 1982, vol. 19, # 11, p. 2061 - 2066
  作者：Tabei, Katsumi、Kawashima, Etsuko、Takada, Toyozo、Kato, Tetsuzo

  DOI：——

  日期：——
• TABEI, KATSUMI;KAWASHIMA, ETSUKO;TAKADA, TOYOZO;KATO, TETSUZO, J. HETEROCYCL. CHEM., 1985, 22, N 2, 569-574
  作者：TABEI, KATSUMI、KAWASHIMA, ETSUKO、TAKADA, TOYOZO、KATO, TETSUZO

  DOI：——

  日期：——