3-hydroxy-2-oxo-3-azetidinepropanoic acid benzyl ester | 144373-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-hydroxy-2-oxo-3-azetidinepropanoic acid benzyl ester
• 英文别名: Benzyl 3-(3-hydroxy-2-oxoazetidin-3-yl)propanoate
• CAS: 144373-45-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: ZMBLAQRDDGZPLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-oxo-3-azetidinepropanoic acid benzyl ester 以92%的产率得到
  参考文献：
  名称：

  Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzyl 3-[1-[tert-butyl(dimethyl)silyl]-2-oxo-3-trimethylsilyloxyazetidin-3-yl]-2-trimethylsilylpropanoate 以87%的产率得到
  参考文献：
  名称：

  Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884

  摘要：

  DOI：

文献信息

• ATP-citrate-lyase as a target for hypolipidemic intervention. Sulfoximine and 3-hydroxy-.beta.-lactam containing analogs of citric acid as potential tight-binding inhibitors
  作者：Roland E. Dolle、David McNair、Mark J. Hughes、Lawrence I. Kruse、Drake Eggelston、Barbara A. Saxty、Timothy N. C. Wells、Pieter H. E. Groot

  DOI：10.1021/jm00104a014

  日期：1992.12

  Citric acid analogues (+/-)-12a,b and (+/-)-17a,b, where one of the primary carboxylates has been replaced by a sulfoximinoyl and a 3-(3-hydroxy-beta-lactamyl) moiety, respectively, have been synthesized and evaluated as inhibitors of ATP-citrate lyase. The design of these inhibitors was based on methionine sulfoximine and tabtoxinine beta-lactam, potent, tight-binding inhibitors of glutamine synthetase. Both ATP-citrate lyase and glutamine synthetase employ phosphate-carboxylate anhydrides as a method for carboxylate activation during catalysis. Only one diastereomer, (+/-)-12a, displayed weak, reversible inhibition, while the remaining citrate analogues (+/-)-12b and (+/-)-17a,b were inactive against the lyase. No time-dependent inactivation of the enzyme was observed.
• Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884
  作者：Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+

  DOI：——

  日期：——