[(3S,2R)-3-amino-2-hydroxy-4-phenylbutyl]azide | 165331-67-9

• 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,2R)-3-amino-2-hydroxy-4-phenylbutyl]azide
• 英文别名: (2R,3S)-3-amino-1-azido-4-phenylbutan-2-ol
• CAS: 165331-67-9
• 化学式: C₁₀H₁₄N₄O
• 分子量: 206.247
• InChiKey: GTLBAINPYSXKOY-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3S,2R)-3-amino-2-hydroxy-4-phenylbutyl]azide 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 60.0 ℃ 、275.79 kPa 条件下， 生成 {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
  参考文献：
  名称：

  Novel arylsulfonamides possessing sub-picomolar HIV protease activities and potent anti-HIV activity against wild-type and drug-resistant viral strains

  摘要：

  A novel series of P1' chain-extended arylsufonamides was synthesiszed and evaluated for wild-type HIV protease inhibitory activity and in vitro antiviral activity against wild type virus and two protease inhibitor-resistant mutant viruses. All of the compounds showed dramatic increases in enzyme activity as compared to the currently marketed HIV protease inhibitors amprenavir, indinavir, and nelfinavir. In addition, significant improvements in antiviral potencies against wild type and the two mutant viruses were also realized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.008
• 作为产物：
  描述：

  1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 在 盐酸 、 sodium azide 、 氯化铵 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 [(3S,2R)-3-amino-2-hydroxy-4-phenylbutyl]azide
  参考文献：
  名称：

  Synthesis and absolute configuration of (+)-2,3,3-trimethyl-2-hydroxybutanoic acid

  摘要：

  The absolute configuration of (+)-2,3,3-trimethyl-2-hydroxybutanoic acid, a key intermediate in the synthesis of the HIV-protease inhibitor 1a (isomer A), has been confirmed as (R) on the basis of X-ray analysis.

  DOI：

  10.1016/0957-4166(95)00378-9

文献信息

• HIV protease inhibiting compounds
  申请人：Flentge Charles A.

  公开号：US20110003827A1

  公开（公告）日：2011-01-06

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

  公开了一种具有以下公式的化合物，作为HIV蛋白酶抑制剂。还公开了抑制HIV感染的方法和组合物。
• Inhibitors of aspartyl protease
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20020198388A1

  公开（公告）日：2002-12-26

  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.

  本发明涉及一种新型磺酰胺类物质，其为天冬氨酸蛋白酶抑制剂。在一种实施例中，本发明涉及一种新型的HIV天冬氨酸蛋白酶抑制剂，其具有特定的结构和物理化学特征。本发明还涉及包含这些化合物的制药组合物。本发明的化合物和制药组合物特别适合于抑制HIV-1和HIV-2蛋白酶活性，因此可以作为抗HIV-1和HIV-2病毒的抗病毒剂优势使用。本发明还涉及使用本发明化合物抑制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。
• HIV PROTEASE INHIBITING COMPOUNDS
  申请人：Flentge Charles A.

  公开号：US20130023463A1

  公开（公告）日：2013-01-24

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

  该化合物的公式被披露为HIV蛋白酶抑制剂。还披露了抑制HIV感染的方法和组合物。
• HYDROXYETHYLAMINO SULFONAMIDE DERIVATIVES
  申请人：Harbeson Scott L.

  公开号：US20100305173A1

  公开（公告）日：2010-12-02

  This invention relates to novel hydroxyethylamino sulfonamides, their derivatives, pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a compound with the ability to act as an HIV (human immunodeficiency virus) protease inhibitor.

  本发明涉及一种新型的羟乙基氨基磺酰胺及其衍生物、其药学上可接受的盐。本发明还提供了包含本发明化合物的组合物，并使用这些组合物治疗通过给予具有作为HIV（人类免疫缺陷病毒）蛋白酶抑制剂能力的化合物有益的疾病和病况的方法。
• Hiv protease inhibiting sulfonamides
  申请人：Abbott Laboratories

  公开号：EP2216334A1

  公开（公告）日：2010-08-11

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

  式中的化合物 公开了一种 I-IIV 蛋白酶抑制剂。还公开了抑制艾滋病毒感染的方法和组合物。