(S)-2-Amino-2-(2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-1-((S)-3-fluoro-pyrrolidin-1-yl)-ethanone | 676517-23-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Amino-2-(2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-1-((S)-3-fluoro-pyrrolidin-1-yl)-ethanone
• 英文别名: (2S)-2-amino-2-(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)-1-[(3S)-3-fluoropyrrolidin-1-yl]ethanone
• CAS: 676517-23-0
• 化学式: C₁₃H₁₉FN₄OS
• 分子量: 298.384
• InChiKey: WHOXJXRVTHVXEZ-ZEMFGHSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-2-(2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-1-((S)-3-fluoro-pyrrolidin-1-yl)-ethanone 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 {(S)-2-((S)-3-Fluoro-pyrrolidin-1-yl)-1-[2-(4-fluoro-3-trifluoromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzothiazol-6-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Heterocycle Fused Cyclohexyl-glycine Derivatives as Novel Dipeptidyl Peptidase-IV Inhibitors

  摘要：

  A new class of potent inhibitors of dipeptidyl peptidase IV (DP-IV) for the treatment of type II diabetes are described. Presented herein is the synthesis of indole-fused and thiazole-fused cyclohexylglycines. Pyrrolidine-derived amides of these novel heterocycles led to the discovery of thiazole derivatives (3f) and (11a), both low nanomolar inhibitors of DP-IV (IC50 = 6 nM).

  DOI：

  10.3987/com-03-s(p)50
• 作为产物：
  描述：

  [(S)-2-((S)-3-Fluoro-pyrrolidin-1-yl)-2-oxo-1-(4-oxo-cyclohexyl)-ethyl]-carbamic acid tert-butyl ester 在 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (S)-2-Amino-2-(2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-1-((S)-3-fluoro-pyrrolidin-1-yl)-ethanone
  参考文献：
  名称：

  Heterocycle Fused Cyclohexyl-glycine Derivatives as Novel Dipeptidyl Peptidase-IV Inhibitors

  摘要：

  A new class of potent inhibitors of dipeptidyl peptidase IV (DP-IV) for the treatment of type II diabetes are described. Presented herein is the synthesis of indole-fused and thiazole-fused cyclohexylglycines. Pyrrolidine-derived amides of these novel heterocycles led to the discovery of thiazole derivatives (3f) and (11a), both low nanomolar inhibitors of DP-IV (IC50 = 6 nM).

  DOI：

  10.3987/com-03-s(p)50

文献信息

• Cyclohexylglycine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
  申请人：Edmondson D. Scott

  公开号：US20070021477A1

  公开（公告）日：2007-01-25

  The present invention is directed to novel cyclohexylglycine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.
• US7456204B2
  申请人：——

  公开号：US7456204B2

  公开（公告）日：2008-11-25
• Heterocycle Fused Cyclohexyl-glycine Derivatives as Novel Dipeptidyl Peptidase-IV Inhibitors
  作者：Anthony Mastracchio、Emma R. Parmee、Barbara Leiting、Frank Marsilio、Reshma Patel、Nancy A. Thornberry、Ann E. Weber、Scott D. Edmondson

  DOI：10.3987/com-03-s(p)50

  日期：——

  A new class of potent inhibitors of dipeptidyl peptidase IV (DP-IV) for the treatment of type II diabetes are described. Presented herein is the synthesis of indole-fused and thiazole-fused cyclohexylglycines. Pyrrolidine-derived amides of these novel heterocycles led to the discovery of thiazole derivatives (3f) and (11a), both low nanomolar inhibitors of DP-IV (IC50 = 6 nM).