(4R,5S)-4-氨基-3-氧代-1,2-恶唑烷-5-甲酰胺 | 66620-06-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (4R,5S)-4-氨基-3-氧代-1,2-恶唑烷-5-甲酰胺
• 英文名称: 4t-amino-3-oxo-isoxazolidine-5r-carboxylic acid amide
• 英文别名: (4R,5S)-4-Amino-3-oxoisoxazolidine-5-carboxamide；(4R,5S)-4-amino-3-oxo-1,2-oxazolidine-5-carboxamide
• CAS: 66620-06-2
• 化学式: C₄H₇N₃O₃
• 分子量: 145.118
• InChiKey: GDJHRXTXBJAERL-NCGGTJAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-氨基-3-氧代-1,2-恶唑烷-5-甲酰胺 在 platinum(IV) oxide 氢气 作用下， 生成 DL-erythro-3-hydroxy-aspartic acid diamide
  参考文献：
  名称：

  5-Carboxamido-4-amino-3-isoxazolidone, an asparagine analog

  摘要：

  trans-Aziridine-2,3-dicarboxylic ester was used to prepare the required beta-chlorohydroxamic acid used in the synthesis of the title compound. The trans configuration of the asparagine analogue was established by hydrogenolysis to erythro-beta-hydroxyasparagine amide. Neither the title compound nor the intermediate aziridinehydroxamic acid (8) showed significant activity against the L1210 and P-388 tumors. The title compound was inactive as an inhibitor of asparagine synthetase from Novikoff hepatoma and did not inhibit the growth of some 25 bacteria and fungi.

  DOI：

  10.1021/jm00205a026
• 作为产物：
  描述：

  4t-amino-3-oxo-isoxazolidine-5r-carboxylic acid methyl ester 在 ammonium hydroxide 作用下， 生成 (4R,5S)-4-氨基-3-氧代-1,2-恶唑烷-5-甲酰胺
  参考文献：
  名称：

  5-Carboxamido-4-amino-3-isoxazolidone, an asparagine analog

  摘要：

  trans-Aziridine-2,3-dicarboxylic ester was used to prepare the required beta-chlorohydroxamic acid used in the synthesis of the title compound. The trans configuration of the asparagine analogue was established by hydrogenolysis to erythro-beta-hydroxyasparagine amide. Neither the title compound nor the intermediate aziridinehydroxamic acid (8) showed significant activity against the L1210 and P-388 tumors. The title compound was inactive as an inhibitor of asparagine synthetase from Novikoff hepatoma and did not inhibit the growth of some 25 bacteria and fungi.

  DOI：

  10.1021/jm00205a026

文献信息

• 5-Carboxamido-4-amino-3-isoxazolidone, an asparagine analog
  作者：Charles H. Stammer、Masayuki Sato

  DOI：10.1021/jm00205a026

  日期：1978.7

  trans-Aziridine-2,3-dicarboxylic ester was used to prepare the required beta-chlorohydroxamic acid used in the synthesis of the title compound. The trans configuration of the asparagine analogue was established by hydrogenolysis to erythro-beta-hydroxyasparagine amide. Neither the title compound nor the intermediate aziridinehydroxamic acid (8) showed significant activity against the L1210 and P-388 tumors. The title compound was inactive as an inhibitor of asparagine synthetase from Novikoff hepatoma and did not inhibit the growth of some 25 bacteria and fungi.