8-cyclobutanecarbonyl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one | 1386443-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-cyclobutanecarbonyl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one
• CAS: 1386443-14-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: DMQKIYUXLCTQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-cyclobutanecarbonyl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到8-(cyclobutyl-hydroxymethyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one
  参考文献：
  名称：

  Novel Imidazol-1-ylmethyl Substituted 1,2,5,6-Tetrahydropyrrolo[3,2,1-ij]quinolin-4-ones as Potent and Selective CYP11B1 Inhibitors for the Treatment of Cushing’s Syndrome

  摘要：

  CYP11B1 inhibition is a promising therapy for Cushing's syndrome. Starting from etomidate, references I and II, the title compounds were designed and synthesized. Cyclopropyl analogue 4 was identified as a CYP11B1 inhibitor more potent (IC50 = 2.2 nM) than leads and more selective (SF = 11) than I and metyrapone. Since it also showed potent inhibition of rat CYP11B1 and good selectivity over human CYP17 and CYP19, it is a promising candidate for further development.

  DOI：

  10.1021/jm3003872
• 作为产物：
  描述：

  咯喹酮 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 六正丁基二锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 8-cyclobutanecarbonyl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one
  参考文献：
  名称：

  Novel Imidazol-1-ylmethyl Substituted 1,2,5,6-Tetrahydropyrrolo[3,2,1-ij]quinolin-4-ones as Potent and Selective CYP11B1 Inhibitors for the Treatment of Cushing’s Syndrome

  摘要：

  CYP11B1 inhibition is a promising therapy for Cushing's syndrome. Starting from etomidate, references I and II, the title compounds were designed and synthesized. Cyclopropyl analogue 4 was identified as a CYP11B1 inhibitor more potent (IC50 = 2.2 nM) than leads and more selective (SF = 11) than I and metyrapone. Since it also showed potent inhibition of rat CYP11B1 and good selectivity over human CYP17 and CYP19, it is a promising candidate for further development.

  DOI：

  10.1021/jm3003872