ethyl (2R)-2-(2-phenylethyl)oxirane-2-carboxylate | 1268152-06-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2R)-2-(2-phenylethyl)oxirane-2-carboxylate
• CAS: 1268152-06-2
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: FMBQPYLGRUOWBQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2R)-2-(2-phenylethyl)oxirane-2-carboxylate 在 乙醇 、 potassium hydroxide 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (R)-2-phenethyloxirane-2-carboxylic acid
  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：

  2-phenethyloxirane-2-carboxylic acid ethyl ester 在 Reprosil Chiral NR column 作用下， 以 2-甲基戊烷 、 异丙醇 为溶剂， 生成 ethyl (2S)-2-(2-phenylethyl)oxirane-2-carboxylate 、 ethyl (2R)-2-(2-phenylethyl)oxirane-2-carboxylate
  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