methyl 4-(3-bromo-4-fluorophenyl)-4,5,6,7-tetrahydro-2-methyl-5-oxo-1H-cyclopenta[b]pyridine-3-carboxylate | 265994-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(3-bromo-4-fluorophenyl)-4,5,6,7-tetrahydro-2-methyl-5-oxo-1H-cyclopenta[b]pyridine-3-carboxylate
• 英文别名: methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate；methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,6,7-tetrahydrocyclopenta[b]pyridine-3-carboxylate
• CAS: 265994-08-9
• 化学式: C₁₇H₁₅BrFNO₃
• 分子量: 380.213
• InChiKey: YMNHQSYCTKAAEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  484.6±45.0 °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)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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 4-(3-bromo-4-fluorophenyl)-4,5,6,7-tetrahydro-2-methyl-5-oxo-1H-cyclopenta[b]pyridine-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 醋酸异丙酯 为溶剂， 反应 0.75h， 以1.19 g的产率得到methyl 4-(3-bromo-4-fluorophenyl)-2-(bromomethyl)-4,5,6,7-tetrahydro-5-oxo-1H-cyclopenta[b]pyridine-3-carboxylate
  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：

  3-氨基环戊-2-烯-1-酮 、 乙酰乙酸甲酯 、 3-溴-4-氟苯甲醛 在 甲醇 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以to provide 2.29 g of the title compound的产率得到methyl 4-(3-bromo-4-fluorophenyl)-4,5,6,7-tetrahydro-2-methyl-5-oxo-1H-cyclopenta[b]pyridine-3-carboxylate
  参考文献：
  名称：

  CYCLOPENTANONE DIHYDROPYRIDINE COMPOUNDS USEFUL AS POTASSIUM CHANNEL OPENERS

  摘要：

  公式I1的化合物在治疗由钾通道开放剂预防或改善的疾病方面非常有用。还披露了开放钾通道的组合物和在哺乳动物中开放钾通道的方法。

  公开号：

  US20020007065A1

文献信息

• CYCLOPENTANONE DIHYDROPYRIDINE COMPOUNDS USEFUL AS POTASSIUM CHANNEL OPENERS
  申请人：——

  公开号：US20020007065A1

  公开（公告）日：2002-01-17

  Compounds of formula I 1 are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.

  公式I1的化合物在治疗由钾通道开放剂预防或改善的疾病方面是有用的。同时还披露了钾通道开放组合物以及在哺乳动物中打开钾通道的方法。
• Cyclopentanone dihydropyridine compounds useful as potassium channel openers
  申请人：Abbott Laboratories

  公开号：US06518279B2

  公开（公告）日：2003-02-11

  Compounds of formula I are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.

  I式化合物在治疗由钾通道开放剂预防或缓解的疾病中具有用途。本文还公开了钾通道开放剂组合物和在哺乳动物中开放钾通道的方法。
• US6518279B2
  申请人：——

  公开号：US6518279B2

  公开（公告）日：2003-02-11
• 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.