(2S)-Benzyl 3-(4-benzyloxyphenyl)-2-dibenzylaminopropanoate | 177748-39-9

• 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: (2S)-Benzyl 3-(4-benzyloxyphenyl)-2-dibenzylaminopropanoate
• 英文别名: benzyl (2S)-3-[4-(benzyloxy)phenyl]-2-(dibenzylamino)propanoate；benzyl(2S)-3-[4-(benzyloxy)phenyl]-2-(dibenzylamino)propanoate；benzyl (2S)-2-(dibenzylamino)-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 177748-39-9
• 化学式: C₃₇H₃₅NO₃
• 分子量: 541.69
• InChiKey: WTJWSWJGHZTLLQ-BHVANESWSA-N

物化性质

• 沸点：
  670.7±55.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-Benzyl 3-(4-benzyloxyphenyl)-2-dibenzylaminopropanoate 在 lithium aluminium tetrahydride 、 三氧化硫吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 (S)-2-(N,N-dibenzylamino)-3-(4'-benzyloxyphenyl)-propionaldehyde
  参考文献：
  名称：

  氨基烷基氯代醇盐酸盐的制备：羟乙胺基HIV蛋白酶抑制剂的关键组成部分。

  摘要：

  对映体纯的N，N-二苄基-α-氨基乙醛与（氯甲基）锂发生反应，从溴氯甲烷和锂金属就地生成，主要生成赤型氨基烷基环氧化物。用盐酸水溶液处理粗环氧化合物，得到结晶（2S，3S）-N，N-二苄基氨基氯醇盐酸盐，总产率为32-56％，且异构体纯度高。这些化合物是用于直接或通过转化为相应的N-Boc-（2S，3S）-氨基烷基环氧化物制备基于羟乙胺的HIV蛋白酶抑制剂的通用合成中间体。所描述的方法不使用危险的试剂或中间体，不需要色谱纯化，因此适合制备大量这些通用模块。

  DOI：

  10.1021/jo960109i
• 作为产物：
  描述：

  溴甲苯 、 L-酪氨酸 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以97%的产率得到(2S)-Benzyl 3-(4-benzyloxyphenyl)-2-dibenzylaminopropanoate
  参考文献：
  名称：

  Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

  摘要：

  将一系列N-苄基三级胺与水合铈铵硝酸盐反应，结果发生N-去苄基化，得到相应的二级胺。在N-苄基酰胺、O-苄基醚、O-苄基酯、O-苄基酚酸盐和S-苄基醚存在的情况下，显示出N-苄基三级胺的化学选择性单N-去苄基化反应的发生。

  DOI：

  10.1039/b006852g

文献信息

• HIV protease inhibiting compounds
  申请人：DeGoey A. David

  公开号：US20050131017A1

  公开（公告）日：2005-06-16

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  公开了一种公式的化合物作为HIV蛋白酶抑制剂。还公开了用于抑制HIV感染的方法和组合物。
• Chemoselective oxidative debenzylation of tertiary N-benzyl amines
  作者：Steven D. Bull、Stephen G. Davies、Andrew W. Mulvaney、R. Shyam Prasad、Andrew D. Smith、Garry Fenton

  DOI：10.1039/b000071j

  日期：——

  Treatment of tertiary amines containing one or more N-benzyl protecting groups with aqueous ceric ammonium nitrate results in clean N-debenzylation to afford the corresponding secondary amine.

  含有一种或多种叔胺的处理 用硝酸高铈铵水溶液保护 N-苄基 导致干净的 N-脱苄基反应以提供相应的 仲胺。
• HIV Protease Inhibiting Compounds
  申请人：DeGoey David A.

  公开号：US20100249181A1

  公开（公告）日：2010-09-30

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  公开了一种化合物，其化学式为，用作HIV蛋白酶抑制剂。还公开了用于抑制HIV感染的方法和组合物。
• Synthesis and identification of unprecedented selective inhibitors of CK1ε
  作者：Gastón Silveira-Dorta、Inês J. Sousa、Miguel X. Fernandes、Victor S. Martín、José M. Padrón

  DOI：10.1016/j.ejmech.2015.03.046

  日期：2015.5

  A small and structure-biased library of enantiopure anti-beta-amino alcohols was prepared in a straightforward manner by a simplified version of the Reetz protocol. Antiproliferative activity testing against a panel of five human solid tumor cell lines gave GI(50) values in the range 1-20 mu M. The reverse screening by computational methods against 58 proteins involved in cancer pointed to kinases as possible therapeutic target candidates. The experimental determination of the interaction with 456 kinases indicated that the compounds behave as selective CK1 epsilon inhibitors. Our results demonstrate that the lead compound represents the first selective CK1 epsilon inhibitor with proven antiproliferative activity in cancer cell lines. (C) 2015 Elsevier Masson SAS. All rights reserved.
• P1-Substituted Symmetry-Based Human Immunodeficiency Virus Protease Inhibitors with Potent Antiviral Activity against Drug-Resistant Viruses
  作者：David A. DeGoey、David J. Grampovnik、Hui-Ju Chen、William J. Flosi、Larry L. Klein、Tatyana Dekhtyar、Vincent Stoll、Mulugeta Mamo、Akhteruzzaman Molla、Dale J. Kempf

  DOI：10.1021/jm201109t

  日期：2011.10.27

  Because there is currently no cure for HIV infection, patients must remain on long-term drug therapy, leading to concerns over potential drug side effects and the emergence of drug resistance. For this reason, new and safe antiretroviral agents with improved potency against drug-resistant strains of HIV are needed. A series of HIV protease inhibitors (PIs) with potent activity against both wild-type (WT) virus and drug-resistant strains of HIV was designed and synthesized. The incorporation of substituents with hydrogen bond donor and acceptor groups at the PI position of our symmetry-based inhibitor series resulted in significant potency improvements against the resistant mutants. By this approach, several compounds, such as 13, 24, and 29, were identified that demonstrated similar or improved potencies compared to 1 against highly mutated strains of HIV derived from patients who previously failed HIV PI therapy. Overall, compound 13 demonstrated the best balance of potency against drug resistant strains of HIV and oral bioavailability in pharmacokinetic studies. X-ray analysis of an HIV PI with an improved resistance profile bound to WT HIV protease is also reported.