[(S)-1-(2-Amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-2-((S)-3-fluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester | 815581-00-1

• 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)-1-(2-Amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-2-((S)-3-fluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(1S)-1-(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)-2-[(3S)-3-fluoropyrrolidin-1-yl]-2-oxoethyl]carbamate
• CAS: 815581-00-1
• 化学式: C₂₁H₂₅FN₄O₃S
• 分子量: 432.519
• InChiKey: XXACBUFYMMQWJL-UFFKYAFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 [(S)-1-(2-Amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-2-((S)-3-fluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester 在 碘代三甲硅烷 作用下， 以 乙腈 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; compound with trifluoro-acetic acid
  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：

  Boc-L-4-hydroxycyclohexylglycine 在 phenyltrimethylammonium tribromide 、 碳酸氢钠 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(S)-1-(2-Amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-2-((S)-3-fluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid benzyl 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

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