prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate | 1414867-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate
• CAS: 1414867-52-9
• 化学式: C₃₀H₃₇N₃O₉
• 分子量: 583.638
• InChiKey: PBTUGXWKEOJHRT-PLIULALBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  191.39
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate 在 四氢吡咯 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以22%的产率得到1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid
  参考文献：
  名称：

  Design and Optimization of Pyrazinecarboxamide-Based Inhibitors of Diacylglycerol Acyltransferase 1 (DGAT1) Leading to a Clinical Candidate Dimethylpyrazinecarboxamide Phenylcyclohexylacetic Acid (AZD7687)

  摘要：

  A new series of pyrazinecarboxamide DGAT1 inhibitors was designed to address the need for a candidate drug with good potency, selectivity, and physical and DMPK properties combined with a low predicted dose in man. Rational design and optimization of this series led to the discovery of compound 30 (AZD7687), which met the project objectives for potency, selectivity, in particular over ACAT1, solubility, and preclinical PK profiles. This compound showed the anticipated excellent pharmacokinetic properties in human volunteers.

  DOI：

  10.1021/jm301296t
• 作为产物：
  描述：

  2-((1R,4R)-4-(4-(((三氟甲基)磺酰基)氧基)苯基)环己基)乙酸甲酯 在 三乙烯二胺 、 1,1'-双(二苯基膦)二茂铁 、 potassium dihydrogenphosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 乙醇 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 37.0h， 生成 prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate
  参考文献：
  名称：

  Design and Optimization of Pyrazinecarboxamide-Based Inhibitors of Diacylglycerol Acyltransferase 1 (DGAT1) Leading to a Clinical Candidate Dimethylpyrazinecarboxamide Phenylcyclohexylacetic Acid (AZD7687)

  摘要：

  A new series of pyrazinecarboxamide DGAT1 inhibitors was designed to address the need for a candidate drug with good potency, selectivity, and physical and DMPK properties combined with a low predicted dose in man. Rational design and optimization of this series led to the discovery of compound 30 (AZD7687), which met the project objectives for potency, selectivity, in particular over ACAT1, solubility, and preclinical PK profiles. This compound showed the anticipated excellent pharmacokinetic properties in human volunteers.

  DOI：

  10.1021/jm301296t