(R)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester | 385836-94-2

• 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: (R)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester
• 英文别名: (R)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester；benzyl {[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methyl}carbamate；Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamate；benzyl N-[[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 385836-94-2
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: QEXXAWVEXVEOJU-LLVKDONJSA-N

物化性质

• 沸点：
  447.4±30.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester 在 盐酸 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以87%的产率得到(R)-3-benzyloxycarbonylamino-2-hydroxypropionic acid
  参考文献：
  名称：

  Novel Glucagon Receptor Antagonists with Improved Selectivity over the Glucose-Dependent Insulinotropic Polypeptide Receptor

  摘要：

  Optimization of a new series of small molecule human glucagon receptor (hGluR) antagonists is described. In the process of optimizing glucagon receptor antagonists, we counter-screened against the closeli related human gastric inhibitory polypeptide receptor (hGIPR), and through structure activity analysis, we obtained compounds with low nanomolar affinities toward the hGluR, which were selective against the hGIPR and the human glucagon-like peptide-1 receptor (hGLP-1R). In the best cases, we obtained a >50 fold selectivity for the hGluR over the hGIPR and a > 1000 fold selectivity over the hGLP-1R. A potent and selective glucagon receptor antagonist was demonstrated to inhibit glucagon-induced glycogenolysis in primary rat hepatocytes as well as to lower glucagon-induced hyperolycemia in Sprague-Dawley rats. Furthermore. the compound was shown to lower blood glucose in the ob/ob mouse after oral dosing.

  DOI：

  10.1021/jm7015599
• 作为产物：
  描述：

  苯甲醇 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 21.5h， 以35%的产率得到(R)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester
  参考文献：
  名称：

  WO2007/57767

  摘要：

  公开号：

文献信息

• Glucagon antagonists/inverse agonists
  申请人：——

  公开号：US20020143186A1

  公开（公告）日：2002-10-03

  A novel class of compounds, which act to antagonize the action of the glucagon hormone on the glucagon receptor. Owing to their antagonizing effect of the glucagon receptor the compounds may be suitable for the treatment and/or prevention of any diseases and disorders, wherein a glucagon antagonistic action is beneficial, such as hyperglycemia, Type 1 diabetes, Type 2 diabetes, disorders of the lipid metabolism, such as dyslipidemia, and obesity.

  一种新型化合物类别，其作用是拮抗胰高血糖素激素对胰高血糖素受体的作用。由于这些化合物对胰高血糖素受体的拮抗作用，这些化合物可能适用于治疗和/或预防任何胰高血糖素拮抗作用有益的疾病和疾病，如高血糖症、1型糖尿病、2型糖尿病、脂质代谢紊乱疾病，如血脂异常和肥胖症。
• [EN] GLUCAGON ANTAGONISTS/INVERSE AGONISTS<br/>[FR] ANTAGONISTES/AGONISTES INVERSES DU GLUCAGON
  申请人：NOVO NORDISK AS

  公开号：WO2002000612A1

  公开（公告）日：2002-01-03

  A novel class of compounds, which act to antagonize the action of the glucagon hormone on the glucagon receptor. Owing to their antagonizing effect of the glucagon receptor the compounds may be suitable for the treatment and/or prevention of any diseases and disorders, wherein a glucagon antagonistic action is beneficial, such as hyperglycemia, Type 1 diabetes, Type 2 diabetes, disorders of the lipid metabolism and obesity.

  一种新型化合物，其作用是对抗胰高血糖素激素对胰高血糖素受体的作用。由于这些化合物对胰高血糖素受体的拮抗作用，因此这些化合物可能适用于治疗和/或预防任何需要胰高血糖素拮抗作用的疾病和障碍，例如高血糖症、1型糖尿病、2型糖尿病、脂质代谢障碍和肥胖症。
• Substituted pyrazoles, compositions containing such compounds and methods of use
  申请人：Parmee Emma

  公开号：US20060084681A1

  公开（公告）日：2006-04-20

  The present invention relates to substituted pyrazoles, compositions containing such compounds and methods of treatment The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes mellitus.

  本发明涉及取代的吡唑，含有这种化合物的组合物和治疗方法。这些化合物是胰高血糖素受体拮抗剂，因此可用于治疗、预防或延迟2型糖尿病的发作。
• Spirocyclic ureas, compositions containing such compounds and methods of use
  申请人：Parmee R. Emma

  公开号：US20060116366A1

  公开（公告）日：2006-06-01

  The present invention relates to spirocyclic ureas, compositions containing such compounds and methods of treatment The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes mellitus.

  本发明涉及螺环脲类化合物、含有此类化合物的组合物以及治疗方法。这些化合物是葡萄糖高原素受体拮抗剂，因此可用于治疗、预防或延迟2型糖尿病的发生。
• SUBSTITUTED PYRAZOLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE
  申请人：Parmee Emma

  公开号：US20090215825A1

  公开（公告）日：2009-08-27

  The present invention relates to substituted pyrazoles, compositions containing such compounds and methods of treatment The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes mellitus.

  本发明涉及取代的吡唑，包含此类化合物的组合物和治疗方法。这些化合物是胰高血糖素受体拮抗剂，因此可用于治疗、预防或延缓2型糖尿病的发生。