(S)-(tetrahydro-furan-3-yl) N-(3-[(4-amino-phenylsulfonyl)-isobutyl-amino]-2-oxo-propyl)-carbamate | 447402-87-1

• 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: (S)-(tetrahydro-furan-3-yl) N-(3-[(4-amino-phenylsulfonyl)-isobutyl-amino]-2-oxo-propyl)-carbamate
• 英文别名: [(3S)-oxolan-3-yl] N-[3-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-2-oxopropyl]carbamate
• CAS: 447402-87-1
• 化学式: C₁₈H₂₇N₃O₆S
• 分子量: 413.495
• InChiKey: BNEDAKBUBIKANV-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-(tetrahydro-furan-3-yl) N-(3-[(4-amino-phenylsulfonyl)-isobutyl-amino]-2-oxo-propyl)-carbamate 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 乙醇 、 正庚烷 、 various solvents 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 {3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-phenylsulfanyl-propyl}-carbamic acid (S)-(tetrahydro-furan-3-yl) ester
  参考文献：
  名称：

  Synthesis and Antiviral Activity of New Anti-HIV Amprenavir Bioisosteres

  摘要：

  Starting from the chemical structure of the recent FDA-approved anti-HIV drug Amprenavir (Agenerase), a potent HIV-protease inhibitor, we have designed new series of Amprenavir bioisoteres in which the methylene group of the benzyl group was replaced by a sulfur atom. This structural modification has required an original multistep synthesis. Unfortunately, introduction of the sulfur atom abolished or drastically decreased both inhibitory activity on recombinant HIV protease and HIV infection protection on MT4 cell cultures.

  DOI：

  10.1021/jm0208323
• 作为产物：
  描述：

  (S)-(tetrahydro-furan-3-yl) N-(3-[isobutyl-[4-nitro-phenylsulfonyl]-amino]-2-oxo-propyl)-carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以47%的产率得到(S)-(tetrahydro-furan-3-yl) N-(3-[(4-amino-phenylsulfonyl)-isobutyl-amino]-2-oxo-propyl)-carbamate
  参考文献：
  名称：

  Synthesis and Antiviral Activity of New Anti-HIV Amprenavir Bioisosteres

  摘要：

  Starting from the chemical structure of the recent FDA-approved anti-HIV drug Amprenavir (Agenerase), a potent HIV-protease inhibitor, we have designed new series of Amprenavir bioisoteres in which the methylene group of the benzyl group was replaced by a sulfur atom. This structural modification has required an original multistep synthesis. Unfortunately, introduction of the sulfur atom abolished or drastically decreased both inhibitory activity on recombinant HIV protease and HIV infection protection on MT4 cell cultures.

  DOI：

  10.1021/jm0208323

文献信息

• Synthesis and Antiviral Activity of New Anti-HIV Amprenavir Bioisosteres
  作者：Luc Rocheblave、Frédéric Bihel、Céline De Michelis、Ghislaine Priem、Jérôme Courcambeck、Brice Bonnet、Jean-Claude Chermann、Jean-Louis Kraus

  DOI：10.1021/jm0208323

  日期：2002.7.1

  Starting from the chemical structure of the recent FDA-approved anti-HIV drug Amprenavir (Agenerase), a potent HIV-protease inhibitor, we have designed new series of Amprenavir bioisoteres in which the methylene group of the benzyl group was replaced by a sulfur atom. This structural modification has required an original multistep synthesis. Unfortunately, introduction of the sulfur atom abolished or drastically decreased both inhibitory activity on recombinant HIV protease and HIV infection protection on MT4 cell cultures.