(2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid | 1013401-21-2

• 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
• 英文名称: (2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid
• 英文别名: phenylthionorstatine；(2R,3R)-3-amino-2-hydroxy-4-phenylsulfanylbutanoic acid
• CAS: 1013401-21-2
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: SBXKOCVYMHUXQE-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of BACE1 inhibitors containing a novel norstatine derivative (2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid

  摘要：

  A novel norstatine derivative, phenylthionorstatine [(2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid; Pins], containing a hydroxymethylcarbonyl (HMC) isostere was designed, synthesized, and stereochemically determined. Then, Pins was introduced into the structure of BACE1 inhibitors at the P-1 position. Finally, Ptns was found as a suitable P-1 moiety for potent BACE1 inhibitor design. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.097
• 作为产物：
  描述：

  在 盐酸 、 sodium hydroxide 、 二甲基硫 、 水 、 苯甲醚 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid
  参考文献：
  名称：

  Design and synthesis of BACE1 inhibitors containing a novel norstatine derivative (2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid

  摘要：

  A novel norstatine derivative, phenylthionorstatine [(2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid; Pins], containing a hydroxymethylcarbonyl (HMC) isostere was designed, synthesized, and stereochemically determined. Then, Pins was introduced into the structure of BACE1 inhibitors at the P-1 position. Finally, Ptns was found as a suitable P-1 moiety for potent BACE1 inhibitor design. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.097

文献信息

• PEPTIDE DERIVATIVES HAVING BETA-SECRETASE INHIBITORY ACTIVITY
  申请人：Kiso, Yoshiaki

  公开号：EP1600457B1

  公开（公告）日：2013-02-20
• Design and synthesis of BACE1 inhibitors containing a novel norstatine derivative (2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid
  作者：Zyta Ziora、Soko Kasai、Koushi Hidaka、Ayaka Nagamine、Tooru Kimura、Yoshio Hayashi、Yoshiaki Kiso

  DOI：10.1016/j.bmcl.2006.12.097

  日期：2007.3

  A novel norstatine derivative, phenylthionorstatine [(2R,3R)-3-amino-2-hydroxy-4-(phenylthio)butyric acid; Pins], containing a hydroxymethylcarbonyl (HMC) isostere was designed, synthesized, and stereochemically determined. Then, Pins was introduced into the structure of BACE1 inhibitors at the P-1 position. Finally, Ptns was found as a suitable P-1 moiety for potent BACE1 inhibitor design. (c) 2007 Elsevier Ltd. All rights reserved.