(2R',4R)-({[4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinyl]carbonyl}oxy)(phenyl)ethanoic acid | 265994-11-4

• 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: (2R',4R)-({[4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinyl]carbonyl}oxy)(phenyl)ethanoic acid
• 英文别名: (2R)-2-[(4R)-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carbonyl]oxy-2-phenylacetic acid
• CAS: 265994-11-4
• 化学式: C₂₅H₂₁BrFNO₅
• 分子量: 514.348
• InChiKey: JTUSZZQQCXQEGT-JTHBVZDNSA-N

物化性质

• 沸点：
  647.3±55.0 °C(predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R',4R)-({[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 17.0h， 生成 (9R)-9-(3-bromo-4-fluorophenyl)-3,4,5,6,7,9-hexahydrofuro[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：

  methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate 在 氯化亚砜 、 三氯化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2R',4R)-({[4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinyl]carbonyl}oxy)(phenyl)ethanoic acid
  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

文献信息

• Synthesis and Structure−Activity Relationships of a Novel Series of Tricyclic Dihydropyridine-Based K_ATP Openers That Potently Inhibit Bladder Contractions in Vitro
  作者：William A. Carroll、Konstantinos A. Agrios、Robert J. Altenbach、Steven A. Buckner、Yiyuan Chen、Michael J. Coghlan、Anthony V. Daza、Irene Drizin、Murali Gopalakrishnan、Rodger F. Henry、Michael E. Kort、Philip R. Kym、Ivan Milicic、Jamie C. Smith、Rui Tang、Sean C. Turner、Kristi L. Whiteaker、Henry Zhang、James P. Sullivan

  DOI：10.1021/jm030357o

  日期：2004.6.1

  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.