(3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid | 390377-67-0

• 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: (3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid
• 英文别名: (3S,4S)-4-(dibenzylamino)-3-hydroxy-5-phenylpentanoic acid
• CAS: 390377-67-0
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: FIAJCVPNNFSBMD-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid 在 palladium hydroxide - carbon 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 22.0h， 以99%的产率得到(3S,4s)-4-氨基-3-羟基-5-苯基戊酸
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

  摘要：

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00804-3
• 作为产物：
  描述：

  苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

  摘要：

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00804-3

文献信息

• Cyanobacterial peptides as a prototype for the design of cathepsin D inhibitors
  作者：Hao Xu、Keting Bao、Shuai Tang、Jing Ai、Haiyan Hu、Wei Zhang

  DOI：10.1002/psc.3014

  日期：2017.9

  Cathepsin D (Cath D) is overexpressed and secreted in a number of solid tumors and involved in the progress of tumor invasion, proliferation, metastasis, and apoptosis. Inhibition of Cath D is regarded as an attractive pathway for the development of novel anticancer drugs. Our previous studies revealed that tasiamide B, a cyanobacterial peptide that contained a statine‐like unit, exhibited good inhibition

  组织蛋白酶D（Cath D）在许多实体瘤中过度表达和分泌，并参与肿瘤侵袭，增殖，转移和凋亡的进程。抑制Cath D被认为是开发新型抗癌药物的诱人途径。我们以前的研究表明，含有他汀类单元的蓝细菌肽tasiamide B对Cath D和其他天冬氨酸蛋白酶表现出良好的抑制作用。使用该天然产物，为原型，我们设计并合成了三个新的类似物，其承担间苯二甲酸片段在Ñ -末端和异丁基胺（1），环丙基胺（2），或3-甲氧基苄基胺（3）部分在Ç终点站。酶法分析表明，这三种化合物均对Cath D表现出中等至良好的抑制作用，IC 50分别为15、884和353 nM。值得注意的是，化合物1对Cath D具有极高的选择性，比Cath E高576倍，比BACE1高554倍，这对于设计高效和选择性Cath D抑制剂可能是有价值的模板。此外，化合物1对HeLa细胞系的活性中等，IC 50为41.8μM。版权所有©2017欧洲多肽协会和John
• Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes
  作者：José M Andrés、Rafael Pedrosa、Alberto Pérez、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4020(01)00804-3

  日期：2001.10

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.