4-[hydroxy-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-methyl]-benzonitrile | 1386443-33-9

• 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: 4-[hydroxy-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-methyl]-benzonitrile
• CAS: 1386443-33-9
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: IRPCRGLJCTUTAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  咪唑 、 4-[hydroxy-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-methyl]-benzonitrile 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以56%的产率得到4-[(2,4,5,6-tetrahydro-4-oxo-1H-pyrrolo[3,2,1-ij]quinolin-8-yl)(1H-imidazol-1-yl)methyl]benzonitrile
  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：

  4-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carbonyl)-benzonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以67%的产率得到4-[hydroxy-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-methyl]-benzonitrile
  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