tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate | 854754-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate
• 英文别名: tert-butyl N-[(2S,4S,5S)-5-amino-4-hydroxy-1-phenyl-6-(4-pyridin-2-ylphenyl)hexan-2-yl]carbamate
• CAS: 854754-98-6
• 化学式: C₂₈H₃₅N₃O₃
• 分子量: 461.604
• InChiKey: JPAOAXNAMKOZRW-GNKBHMEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate 、 N-甲氧羰基-L-叔亮氨酸 在 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以56%的产率得到tert-butyl (1S,3S,4S)-1-benzyl-3-hydroxy-4-({(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}amino)-5-[4-(2-pyridinyl)phenyl]pentylcarbamate
  参考文献：
  名称：

  HIV protease inhibiting compounds

  摘要：

  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。

  公开号：

  US20050131017A1
• 作为产物：
  描述：

  tert-butyl (2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1-phenyl-6-(4-(pyridin-2-yl)phenyl)hexan-2-ylcarbamate 在 盐酸 、 palladium hydroxide on carbon 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 乙酸乙酯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate
  参考文献：
  名称：

  2-Pyridyl P1′-Substituted Symmetry-Based Human Immunodeficiency Virus Protease Inhibitors (A-792611 and A-790742) with Potential for Convenient Dosing and Reduced Side Effects

  摘要：

  A series of symmetry-based HIV protease inhibitors was designed and synthesized. Modification of the core regiochemistry and stereochemistry significantly affected the potency, metabolic stability, and oral bioavailability of the inhibitors, as did the variation of a pendent arylmethyl P3 group. Optimization led to the selection of two compounds, 10c (A-790742) and 9d (A-792611), for advancement to preclinical studies. Both compounds displayed low nanomolar potency against wild type HIV in the presence of human serum, low rates of metabolism in human liver microsomes, and high oral bioavailability in animal models. The compounds were examined in a preclinical model for the hyperbilirubinemia observed with some HIV PIs, and both exhibited less bilirubin elevation than comparator compounds. X-ray crystallographic analyses of the new cores were used to examine differences in their binding modes. The antiviral activity of the compounds against protease inhibitor resistant strains of HIV was also determined.

  DOI：

  10.1021/jm900044w

文献信息

• HIV Protease Inhibiting Compounds
  申请人：AbbVie Inc.

  公开号：US20140194349A1

  公开（公告）日：2014-07-10

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

  一种化合物公式如下所示，作为HIV蛋白酶抑制剂被揭示。还揭示了用于抑制HIV感染的方法和组合物。