1-tert-butoxycarbonyl-2(S)-[2-phenylsulphonyl-(E)-ethenyl]pyrrolidine | 272129-63-2

• 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: 1-tert-butoxycarbonyl-2(S)-[2-phenylsulphonyl-(E)-ethenyl]pyrrolidine
• 英文别名: tert-butyl (2S)-2-[(E)-2-(benzenesulfonyl)ethenyl]pyrrolidine-1-carboxylate
• CAS: 272129-63-2
• 化学式: C₁₇H₂₃NO₄S
• 分子量: 337.44
• InChiKey: RWFXJNBRONWHJA-CMPYXILNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-tert-butoxycarbonyl-2(S)-[2-phenylsulphonyl-(E)-ethenyl]pyrrolidine 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 benzyl N-[(2S)-1-[[2-[(2S)-2-[(E)-2-(benzenesulfonyl)ethenyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and activity of pyrrolidinyl- and thiazolidinyl-dipeptide derivatives as inhibitors of the Tc80 prolyl oligopeptidase from Trypanosoma cruzi

  摘要：

  Pyrrolidinyl- and thiazolidinyl- dipeptide derivatives, featuring either a vinyl sulfone-, a 2-ketobenzothiazole-, a nitrile-, or a benzimidazole group at the C-terminus, were designed and synthesized as potential inhibitors of the prolyl-specific Tc80 proteinase from Trypanosoma cruzi, the agent of Chagas' disease. These compounds were evaluated in vitro towards the target enzyme which was classified as a serine protease belonging to the prolyl oligopeptidase family (EC 3.4.21.26). A peptidyl nitrile and two peptidyl alpha-ketobenzothiazoles were shown to be potent reversible and competitive inhibitors of Tc 80 proteinase, with K-i values in the range 38-219 nM, and compared advantageously with some known mammalian prolyl oligopeptidase inhibitors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00118-5
• 作为产物：
  描述：

  苯砜基甲基膦酸二乙酯 、 (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到1-tert-butoxycarbonyl-2(S)-[2-phenylsulphonyl-(E)-ethenyl]pyrrolidine
  参考文献：
  名称：

  Synthesis and activity of pyrrolidinyl- and thiazolidinyl-dipeptide derivatives as inhibitors of the Tc80 prolyl oligopeptidase from Trypanosoma cruzi

  摘要：

  Pyrrolidinyl- and thiazolidinyl- dipeptide derivatives, featuring either a vinyl sulfone-, a 2-ketobenzothiazole-, a nitrile-, or a benzimidazole group at the C-terminus, were designed and synthesized as potential inhibitors of the prolyl-specific Tc80 proteinase from Trypanosoma cruzi, the agent of Chagas' disease. These compounds were evaluated in vitro towards the target enzyme which was classified as a serine protease belonging to the prolyl oligopeptidase family (EC 3.4.21.26). A peptidyl nitrile and two peptidyl alpha-ketobenzothiazoles were shown to be potent reversible and competitive inhibitors of Tc 80 proteinase, with K-i values in the range 38-219 nM, and compared advantageously with some known mammalian prolyl oligopeptidase inhibitors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00118-5

文献信息

• Synthesis and activity of pyrrolidinyl- and thiazolidinyl-dipeptide derivatives as inhibitors of the Tc80 prolyl oligopeptidase from Trypanosoma cruzi
  作者：Roger Joyeau、Chanfi Maoulida、Cindy Guillet、François Frappier、Antonio R.L. Teixeira、Joseph Schrével、Jaime Santana、Philippe Grellier

  DOI：10.1016/s0223-5234(00)00118-5

  日期：2000.2

  Pyrrolidinyl- and thiazolidinyl- dipeptide derivatives, featuring either a vinyl sulfone-, a 2-ketobenzothiazole-, a nitrile-, or a benzimidazole group at the C-terminus, were designed and synthesized as potential inhibitors of the prolyl-specific Tc80 proteinase from Trypanosoma cruzi, the agent of Chagas' disease. These compounds were evaluated in vitro towards the target enzyme which was classified as a serine protease belonging to the prolyl oligopeptidase family (EC 3.4.21.26). A peptidyl nitrile and two peptidyl alpha-ketobenzothiazoles were shown to be potent reversible and competitive inhibitors of Tc 80 proteinase, with K-i values in the range 38-219 nM, and compared advantageously with some known mammalian prolyl oligopeptidase inhibitors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.