{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-chloro-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester | 681028-79-5

• 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: {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-chloro-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
• CAS: 681028-79-5
• 化学式: C₃₂H₄₃ClN₂O₉S
• 分子量: 667.22
• InChiKey: NBBICDFEQQWBRZ-UGSBDYSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  132.86
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-chloro-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 在 镍 氨 、 氢气 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 60.0 ℃ 、275.79 kPa 条件下， 生成 [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-3-[(7-amino-2,2-dimethyl-heptyl)-(1,3-benzodioxol-5-ylsulfonyl)amino]-1-benzyl-2-hydroxy-propyl]carbamate
  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 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 100.0 ℃ 、275.79 kPa 条件下， 生成 {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-chloro-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