(6CI)-1-丁基-1,2,3,4-四氢喹噁啉 | 105105-31-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (6CI)-1-丁基-1,2,3,4-四氢喹噁啉
• 英文名称: 1-butyl-1,2,3,4-tetrahydroquinoxaline
• 英文别名: 1-Butyl-1,2,3,4-tetrahydro-chinoxalin；4-butyl-2,3-dihydro-1H-quinoxaline
• CAS: 105105-31-5
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: YLGJUYMPZIRPQB-UHFFFAOYSA-N

物化性质

• 沸点：
  187-191 °C(Press: 21 Torr)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (6CI)-1-丁基-1,2,3,4-四氢喹噁啉 、 在 三乙胺 作用下， 反应 3.0h， 以58%的产率得到C₂₃H₂₂Cl₂N₄O₂
  参考文献：
  名称：

  Design, Synthesis, and Antidiabetic Activity of 4-Phenoxynicotinamide and 4-Phenoxypyrimidine-5-carboxamide Derivatives as Potent and Orally Efficacious TGR5 Agonists

  摘要：

  4-Phenoxynicotinamide and 4-phenoxypyrimidine-5-carboxamide derivatives as potent and orally efficacious TGR5 agonists are reported. Several 4-phenoxynicotinamide derivatives were found to activate human and mouse TGR5 (hTGR5 and mTGR5) with EC50 values in the low nanomolar range. Compound 23g, with an EC50 value of 0.72 nM on hTGR5 and an EC50 value of 6.2 nM on mTGR5, was selected for further in vivo efficacy studies. This compound exhibited a significant dose-dependent glucagon-like peptide-1 (GLP-1) secretion effect. A single oral dose of 23g (50 mg/kg) significantly reduced blood glucose levels in db/db mice and caused a 49% reduction in the area under the blood glucose curve (AUC)(0-120) (min) following an oral glucose tolerance test (OGTT) in imprinting control region (ICR) mice. However, 23g stimulated gallbladder filling, which might result in side effects to the gallbladder.

  DOI：

  10.1021/jm301071h
• 作为产物：
  描述：

  1-benzenesulfonyl-4-butyl-1,2,3,4-tetrahydro-quinoxaline 在 硫酸 作用下， 生成 (6CI)-1-丁基-1,2,3,4-四氢喹噁啉
  参考文献：
  名称：

  1-Alkyl-1,2,3,4-tetrahydroquinoxalines¹

  摘要：

  DOI：

  10.1021/ja01196a015

文献信息

• Convenient Syntheses of 1,2,3,4-Tetrahydroquinoxalines
  作者：RICHARD F. SMITH、WILLIAM J. REBEL、THAISA N. BEACH

  DOI：10.1021/jo01084a014

  日期：1959.2
• Design, Synthesis, and Antidiabetic Activity of 4-Phenoxynicotinamide and 4-Phenoxypyrimidine-5-carboxamide Derivatives as Potent and Orally Efficacious TGR5 Agonists
  作者：Hongliang Duan、Mengmeng Ning、Xiaoyan Chen、Qingan Zou、Liming Zhang、Ying Feng、Lina Zhang、Ying Leng、Jianhua Shen

  DOI：10.1021/jm301071h

  日期：2012.12.13

  4-Phenoxynicotinamide and 4-phenoxypyrimidine-5-carboxamide derivatives as potent and orally efficacious TGR5 agonists are reported. Several 4-phenoxynicotinamide derivatives were found to activate human and mouse TGR5 (hTGR5 and mTGR5) with EC50 values in the low nanomolar range. Compound 23g, with an EC50 value of 0.72 nM on hTGR5 and an EC50 value of 6.2 nM on mTGR5, was selected for further in vivo efficacy studies. This compound exhibited a significant dose-dependent glucagon-like peptide-1 (GLP-1) secretion effect. A single oral dose of 23g (50 mg/kg) significantly reduced blood glucose levels in db/db mice and caused a 49% reduction in the area under the blood glucose curve (AUC)(0-120) (min) following an oral glucose tolerance test (OGTT) in imprinting control region (ICR) mice. However, 23g stimulated gallbladder filling, which might result in side effects to the gallbladder.
• 1-Alkyl-1,2,3,4-tetrahydroquinoxalines¹
  作者：J. C. Cavagnol、F. Y. Wiselogle

  DOI：10.1021/ja01196a015

  日期：1947.4