tert-butyl (4R)-4-(1,3-benzothiazole-2-carbonyl)-1,3-thiazolidine-3-carboxylate | 272129-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: tert-butyl (4R)-4-(1,3-benzothiazole-2-carbonyl)-1,3-thiazolidine-3-carboxylate
• CAS: 272129-65-4
• 化学式: C₁₆H₁₈N₂O₃S₂
• 分子量: 350.463
• InChiKey: KKBUBJZGYOWHQP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-(1,3-benzothiazole-2-carbonyl)-1,3-thiazolidine-3-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以73%的产率得到tert-butyl (4R)-4-[1,3-benzothiazol-2-yl(hydroxy)methyl]-1,3-thiazolidine-3-carboxylate
  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：

  N-Boc-(R)-噻唑-4-羧酸 在 正丁基锂 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl (4R)-4-(1,3-benzothiazole-2-carbonyl)-1,3-thiazolidine-3-carboxylate
  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