3-(3-amino-2-hydroxy-propionylamino)-benzoic acid tert-butyl ester | 1268152-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-amino-2-hydroxy-propionylamino)-benzoic acid tert-butyl ester
• CAS: 1268152-54-0
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: USJROQXQBABPAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101.65
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 3-(3-amino-2-hydroxy-propionylamino)-benzoic acid tert-butyl ester 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Investigation of α-phenylnorstatine and α-benzylnorstatine as transition state isostere motifs in the search for new BACE-1 inhibitors

  摘要：

  Inhibition of the BACE-1 protease enzyme has over the recent decade developed into a promising drug strategy for Alzheimer therapy. In this report, more than 20 new BACE-1 protease inhibitors based on alpha-phenylnorstatine, alpha-benzylnorstatine, iso-serine, and beta-alanine moieties have been prepared. The inhibitors were synthesized by applying Fmoc solid phase methodology and evaluated for their inhibitory properties. The most potent inhibitor, tert-alcohol containing (R)-12 (IC50 = 0.19 mu M) was co-crystallized in the active site of the BACE-1 protease, furnishing a novel binding mode in which the N-terminal amine makes a hydrogen bond to one of the catalytic aspartic acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.042
• 作为产物：
  描述：

  3-(oxiranecarbonyl-amino)-benzoic acid tert-butyl ester 在 氨 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.5h， 生成 3-(3-amino-2-hydroxy-propionylamino)-benzoic acid tert-butyl ester
  参考文献：
  名称：

  Investigation of α-phenylnorstatine and α-benzylnorstatine as transition state isostere motifs in the search for new BACE-1 inhibitors

  摘要：

  Inhibition of the BACE-1 protease enzyme has over the recent decade developed into a promising drug strategy for Alzheimer therapy. In this report, more than 20 new BACE-1 protease inhibitors based on alpha-phenylnorstatine, alpha-benzylnorstatine, iso-serine, and beta-alanine moieties have been prepared. The inhibitors were synthesized by applying Fmoc solid phase methodology and evaluated for their inhibitory properties. The most potent inhibitor, tert-alcohol containing (R)-12 (IC50 = 0.19 mu M) was co-crystallized in the active site of the BACE-1 protease, furnishing a novel binding mode in which the N-terminal amine makes a hydrogen bond to one of the catalytic aspartic acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.042