benzyl 8-iodo-7-oxo-1,2,5,5a,6,7-hexahydro-[1,4]diazepino[1,7-a]quinazoline-3(4H)-carboxylate | 1221408-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: benzyl 8-iodo-7-oxo-1,2,5,5a,6,7-hexahydro-[1,4]diazepino[1,7-a]quinazoline-3(4H)-carboxylate
• CAS: 1221408-12-3
• 化学式: C₂₀H₂₀IN₃O₃
• 分子量: 477.302
• InChiKey: JMTCBQQRZBVOFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.88
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  三甲基环三硼氧烷 、 benzyl 8-iodo-7-oxo-1,2,5,5a,6,7-hexahydro-[1,4]diazepino[1,7-a]quinazoline-3(4H)-carboxylate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以20%的产率得到Benzyl 8-methyl-7-oxo-1,2,5,5a,6,7-hexahydro-[1,4]diazepino[1,7-a]quinazoline-3(4H)-carboxylate
  参考文献：
  名称：

  Tricyclic dihydroquinazolinones as novel 5-HT2C selective and orally efficacious anti-obesity agents

  摘要：

  Agonists of the 5-HT2C receptor have been shown to suppress appetite and reduce body weight in animal models as well as in humans. However, agonism of the related 5-HT2B receptor has been associated with valvular heart disease. Synthesis and biological evaluation of a series of novel and highly selective dihydroquinazolinone-derived 5-HT2C agonists with no detectable agonism of the 5-HT2B receptor is described. Among these, compounds (+)-2a and (+)-3c were identified as potent and highly selective agonists which exhibited weight loss in a rat model upon oral dosing. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.014
• 作为产物：
  描述：

  在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl 8-iodo-7-oxo-1,2,5,5a,6,7-hexahydro-[1,4]diazepino[1,7-a]quinazoline-3(4H)-carboxylate
  参考文献：
  名称：

  Tricyclic dihydroquinazolinones as novel 5-HT2C selective and orally efficacious anti-obesity agents

  摘要：

  Agonists of the 5-HT2C receptor have been shown to suppress appetite and reduce body weight in animal models as well as in humans. However, agonism of the related 5-HT2B receptor has been associated with valvular heart disease. Synthesis and biological evaluation of a series of novel and highly selective dihydroquinazolinone-derived 5-HT2C agonists with no detectable agonism of the 5-HT2B receptor is described. Among these, compounds (+)-2a and (+)-3c were identified as potent and highly selective agonists which exhibited weight loss in a rat model upon oral dosing. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.014