8-benzyl-5-(3-bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6(3H,7H)-dione | 265321-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-benzyl-5-(3-bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6(3H,7H)-dione
• 英文别名: 8-benzyl-5-(3-bromo-4-fluorophenyl)-5,7,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6-dione
• CAS: 265321-19-5
• 化学式: C₂₄H₂₀BrFN₂O₃
• 分子量: 483.337
• InChiKey: BZMKCBVYTUNNAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-benzyl-5-(3-bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6(3H,7H)-dione 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 5-(3-bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6(3H,7H)-dione hydrochloride
  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：

  2H-吡喃-3,5(4H,6H)-二酮 在 硫酸 、 氨 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 60.0h， 生成 8-benzyl-5-(3-bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1H-pyrano[3,4-b][1,7]naphthyridine-4,6(3H,7H)-dione
  参考文献：
  名称：

  5‐Amino‐2H‐pyran‐3(6H)‐one, 1, a Convenient Intermediate in the Synthesis of Pyran Containing 1,4‐Dihydropyridines

  摘要：

  5-Amino-2H-pyran-3(6H)-one, 1, is a novel intermediate that is useful in the synthesis of pyran containing dihydropyridines. The synthesis and use of I will be discussed.

  DOI：

  10.1081/scc-120027702

文献信息

• Pyrano, piperidino, and thiopyrano compounds and methods of use
  申请人：Abbott Laboratories

  公开号：US06191140B1

  公开（公告）日：2001-02-20

  The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

  本发明提供了一种新型的化合物，可能在超极化细胞膜、打开钾通道、放松平滑肌细胞和抑制膀胱收缩方面有用，其化学式为I。
• PYRANO, PIPERIDINO, AND THIOPYRANO COMPOUNDS AND METHODS OF USE
  申请人：ABBOTT LABORATORIES

  公开号：EP1124828B1

  公开（公告）日：2008-01-02
• US6191140B1
  申请人：——

  公开号：US6191140B1

  公开（公告）日：2001-02-20
• 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.
• 5‐Amino‐2H‐pyran‐3(6H)‐one, 1, a Convenient Intermediate in the Synthesis of Pyran Containing 1,4‐Dihydropyridines
  作者：Robert J. Altenbach、Konstantinos Agrios、Irene Drizin、William A. Carroll

  DOI：10.1081/scc-120027702

  日期：2004.12.31

  5-Amino-2H-pyran-3(6H)-one, 1, is a novel intermediate that is useful in the synthesis of pyran containing dihydropyridines. The synthesis and use of I will be discussed.