赤配位-N-BOC-苄基-L-酪氨酸环氧化物 | 162536-84-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 赤配位-N-BOC-苄基-L-酪氨酸环氧化物
• 中文别名: 赤式-N-BOC-O-苄基-L-酪氨酸环氧乙烷
• 英文名称: tert-butyl ((S)-2-(4-(benzyloxy)phenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate
• 英文别名: tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate；erythro-N-Boc-O-benzyl-L-tyrosine epoxide；tert-butyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-(4-phenylmethoxyphenyl)ethyl]carbamate
• CAS: 162536-84-7
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: WKKSCOKVTJQVPD-VQTJNVASSA-N

物化性质

• 沸点：
  528.5±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  赤配位-N-BOC-苄基-L-酪氨酸环氧化物 在 palladium on activated charcoal 偶氮二甲酸二叔丁酯 、 氢气 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 生成 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate
  参考文献：
  名称：

  Novel P1 chain-extended HIV protease inhibitors possessing potent anti-HIV activity and remarkable inverse antiviral resistance profiles

  摘要：

  A novel series of tyro si ne-derived HIV protease inhibitors was synthesized and evaluated for in vitro antiviral activity against wild-type virus and two protease inhibitor-resistant viruses. All of the compounds had wild-type antiviral activities that were similar to or greater than several currently marketed HIV protease inhibitors. In addition, a number of compounds in this series were more potent against the drug-resistant mutant viruses than they were against wild-type virus. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.129
• 作为产物：
  描述：

  (2S,3S)-1-(4-(苄氧基)苯基)-4-氯-3-羟基丁烷-2-氨基甲酸叔丁酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 赤配位-N-BOC-苄基-L-酪氨酸环氧化物
  参考文献：
  名称：

  Novel P1 chain-extended HIV protease inhibitors possessing potent anti-HIV activity and remarkable inverse antiviral resistance profiles

  摘要：

  A novel series of tyro si ne-derived HIV protease inhibitors was synthesized and evaluated for in vitro antiviral activity against wild-type virus and two protease inhibitor-resistant viruses. All of the compounds had wild-type antiviral activities that were similar to or greater than several currently marketed HIV protease inhibitors. In addition, a number of compounds in this series were more potent against the drug-resistant mutant viruses than they were against wild-type virus. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.129

文献信息

• Inhibitors of aspartyl protease
  申请人：Vertex Pharmaceuticals Incorporated.

  公开号：US20040122000A1

  公开（公告）日：2004-06-24

  The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.

  本发明涉及一类新型磺胺类化合物，其为天冬氨酸蛋白酶抑制剂。在一个实施例中，本发明涉及一类新型HIV天冬氨酸蛋白酶抑制剂，其具有特定的结构和理化特征。本发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制HIV-1和HIV-2蛋白酶活性，因此，可以有利地用作抗HIV-1和HIV-2病毒的抗病毒剂。本发明还涉及使用本发明的化合物抑制HIV天冬氨酸蛋白酶活性的方法以及筛选具有抗HIV活性的化合物的方法。
• Potent and selective isophthalamide S2 hydroxyethylamine inhibitors of BACE1
  作者：Steven W. Kortum、Timothy E. Benson、Michael J. Bienkowski、Thomas L. Emmons、D. Bryan Prince、Donna J. Paddock、Alfredo G. Tomasselli、Joseph B. Moon、Alice LaBorde、Ruth E. TenBrink

  DOI：10.1016/j.bmcl.2007.03.096

  日期：2007.6

  The design and synthesis of a novel series of potent BACE1 hydroxyethylamine inhibitors. These inhibitors feature hydrogen bonding substituents at the C-5 position of the isophthalamide ring with improved selectivity over cathepsin D.

  设计和合成一系列新型的有效BACE1羟乙基胺抑制剂。这些抑制剂在间苯二甲酰胺环的C-5位置具有氢键取代基，与组织蛋白酶D相比具有更高的选择性。
• Antiviral Compounds
  申请人：University of Massachusetts

  公开号：US20210371439A1

  公开（公告）日：2021-12-02

  The present application provides compounds and methods of treating viral infections, including viral infections caused by HIV or HTLV.

  本申请提供了化合物和治疗病毒感染的方法，包括由HIV或HTLV引起的病毒感染。
• Substituted hydroxyethylamines
  申请人：John Varghese

  公开号：US20060106256A1

  公开（公告）日：2006-05-18

  This invention relates to prodrugs of a class of amine compounds which are useful in the treatment of Alzheimer's disease and similar diseases.

  本发明涉及一类氨基化合物的前药，该类化合物在治疗阿尔茨海默病和类似疾病方面具有用途。
• Compounds to treat alzheimer's disease
  申请人：——

  公开号：US20020128255A1

  公开（公告）日：2002-09-12

  The present invention is substituted amines of formula (X) 1 and of the formula (X′) 2 useful in treating Alzheimer's disease and other similar diseases.

  本发明提供的公式（X）1和公式（X'）2的取代胺在治疗阿尔茨海默病和其他类似疾病中有用。