methyl (4S)-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate | 265994-14-7

• 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: methyl (4S)-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate
• 英文别名: methyl (4S)-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate
• CAS: 265994-14-7
• 化学式: C₁₈H₁₇BrFNO₃
• 分子量: 394.24
• InChiKey: UKWXFDHJGVKEIX-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4S)-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate 在 吡啶 、 pyridinium hydrobromide perbromide 、 氨 作用下， 以 氯仿 为溶剂， 反应 21.0h， 生成 (9S)-9-(3-bromo-4-fluorophenyl)-3,4,5,6,7,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-1,8-dione
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of Tricyclic Dihydropyridine-Based K_ATP Openers That Potently Inhibit Bladder Contractions in Vitro

  摘要：

  Structure-activity relationships were investigated on a novel series of tricyclic dihydropyridine-containing K-ATP openers. This diverse group of analogues, comprising a variety of heterocyclic rings fused to the dihydropyridine nucleus, was designed to determine the influence on activity of hydrogen-bond-donating and -accepting groups and their stereochemical disposition. Compounds were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a subset of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation.

  DOI：

  10.1021/jm030357o
• 作为产物：
  描述：

  甲醇 、 (2R',4S)-({[4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinyl]carbonyl}oxy)(phenyl)ethanoic acid 在 sodium methylate 作用下， 反应 16.0h， 以153 mg的产率得到methyl (4S)-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of Tricyclic Dihydropyridine-Based K_ATP Openers That Potently Inhibit Bladder Contractions in Vitro

  摘要：

  Structure-activity relationships were investigated on a novel series of tricyclic dihydropyridine-containing K-ATP openers. This diverse group of analogues, comprising a variety of heterocyclic rings fused to the dihydropyridine nucleus, was designed to determine the influence on activity of hydrogen-bond-donating and -accepting groups and their stereochemical disposition. Compounds were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a subset of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation.

  DOI：

  10.1021/jm030357o