Ethyl 2-[2-(4-methoxyphenyl)-1,3-oxazol-4-yl]acetate | 84446-02-6

• 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-[2-(4-methoxyphenyl)-1,3-oxazol-4-yl]acetate
• CAS: 84446-02-6
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: APQUYWKQQBBISE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[2-(4-methoxyphenyl)-1,3-oxazol-4-yl]acetate 在 sodium hydroxide 、 水 作用下， 反应 1.0h， 以35%的产率得到2-[2-(4-Methoxyphenyl)-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-(Ethoxycarbonyl)methylene-5,6-dihydro-3-(p-methoxyphenyl)-4H-1,2,4-oxadiazine 以22%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

• LARGE CONDUCTANCE CALCIUM-ACTIVATED K CHANNEL OPENER
  申请人：Hongu Mitsuya

  公开号：US20100256165A1

  公开（公告）日：2010-10-07

  A large conductance calcium-activated K channel opener comprising as an active ingredient a nitrogen-containing 5-membered heterocyclic compound represented by the following formula (I): wherein X represents N—R 4 , O or S, R 1 and R 2 each independently represent hydrogen, halogen, carboxyl, amino, lower alkyl, lower alkoxycarbonyl, lower alkenyl, cyclo-lower alkyl, carbamoyl, aryl, heterocyclic or heterocyclic-substituted carbonyl group, R 3 represents aryl, heterocyclic or lower alkyl group, and R 4 represents hydrogen or lower alkyl group, or a pharmaceutically acceptable salt thereof.

  一种大导电性钙激活的K通道开放剂，其作为活性成分是一种含氮的5元杂环化合物，表示为以下式子（I）：其中X代表N—R4，O或S，R1和R2各自独立地表示氢、卤素、羧基、氨基、低碳基、低碳氧基羰基、低烯基、环-低碳基、氨基甲酰基、芳基、杂环或杂环取代的羰基基团，R3表示芳基、杂环或低碳基团，R4表示氢或低碳基团，或其药学上可接受的盐。
• 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, HETEROCYCLES, 1982, 19, N 11, 2061-2066
  作者：TABEI, KATSUMI、KAWASHIMA, ETSUKO、TAKADA, TOYOZO、KATO, TETSUZO

  DOI：——

  日期：——
• US7759373B2
  申请人：——

  公开号：US7759373B2

  公开（公告）日：2010-07-20