benzyl [(1S)-2-oxo-1-(4-oxocyclohexyl)-2-pyrrolidinylethyl]carbamate | 676517-00-3

• 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: benzyl [(1S)-2-oxo-1-(4-oxocyclohexyl)-2-pyrrolidinylethyl]carbamate
• 英文别名: benzyl N-[(1S)-2-oxo-1-(4-oxocyclohexyl)-2-pyrrolidin-1-ylethyl]carbamate
• CAS: 676517-00-3
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: XCBSFSJWCOJZQY-SFHVURJKSA-N

物化性质

• 沸点：
  582.6±35.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl [(1S)-2-oxo-1-(4-oxocyclohexyl)-2-pyrrolidinylethyl]carbamate 在 palladium dihydroxide 氢气 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 (S)-2-Amino-1-pyrrolidin-1-yl-2-(6-trifluoromethoxy-2,3,4,9-tetrahydro-1H-carbazol-3-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：

  [(S)-2-Oxo-1-(4-oxo-cyclohexyl)-2-pyrrolidin-1-yl-ethyl]-carbamic acid tert-butyl ester 在 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 benzyl [(1S)-2-oxo-1-(4-oxocyclohexyl)-2-pyrrolidinylethyl]carbamate
  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

• [EN] FUSED INDOLES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] INDOLES FUSIONNES EN TANT QU'INHIBITEURS DE DIPEPTIDYLE PEPTIDASE DESTINES AU TRAITEMENT OU A LA PREVENTION DES DIABETES
  申请人：MERCK & CO INC

  公开号：WO2004110436A1

  公开（公告）日：2004-12-23

  The present invention is directed to fused indole 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.

  本发明涉及融合的吲哚衍生物，其是二肽基肽酶-IV酶（“DP-IV抑制剂”）的抑制剂，并且在治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病和特别是2型糖尿病方面非常有用。本发明还涉及包含这些化合物的制药组合物，以及在预防或治疗二肽基肽酶-IV酶参与的这些疾病方面使用这些化合物和组合物。
• US7332520B2
  申请人：——

  公开号：US7332520B2

  公开（公告）日：2008-02-19
• 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).