6-Bromo-2-(3,4-dichlorophenyl)-2H-pyrano<2,3-b>pyridine | 102830-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 6-Bromo-2-(3,4-dichlorophenyl)-2H-pyrano<2,3-b>pyridine
• 英文别名: 6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine
• CAS: 102830-82-0
• 化学式: C₁₄H₈BrCl₂NO
• 分子量: 357.034
• InChiKey: KUQJOQDSCMXOEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  100.5-101.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  453.4±45.0 °C(Predicted)
• 密度：
  1.637±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Bromo-2-(3,4-dichlorophenyl)-2H-pyrano<2,3-b>pyridine 在 W-2 Raney Ni 甲醇 、 氢气 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.33h， 生成 2-(3,4-Dichlorophenyl)-3,4-dihydro-2H-pyrano<2,3-b>pyridine
  参考文献：
  名称：

  3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity

  摘要：

  A general synthesis to the title compounds 1, substituted in the 6-position and on the phenyl ring, is outlined. Eighteen analogues were compared with respect to in vitro activity against rhinovirus types 1A, 9, and 64. Compounds 1c and 1h, the 6-bromo- and 6-(methylsulfonyl)-3',4'-dichlorophenyl analogues, afforded median MIC50 values against 23 rhinovirus serotypes of 0.05 and 0.13 micrograms/mL, respectively. Mice dosed orally with 200 mg/kg of 1c or 1h exhibited serum levels well in excess of each compound's MIC50, indicating that some analogues have the potential to be orally effective drugs.

  DOI：

  10.1021/jm00159a006
• 作为产物：
  描述：

  2-甲氧基吡啶 在 正丁基锂 、 氢溴酸 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 22.5h， 生成 6-Bromo-2-(3,4-dichlorophenyl)-2H-pyrano<2,3-b>pyridine
  参考文献：
  名称：

  3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity

  摘要：

  A general synthesis to the title compounds 1, substituted in the 6-position and on the phenyl ring, is outlined. Eighteen analogues were compared with respect to in vitro activity against rhinovirus types 1A, 9, and 64. Compounds 1c and 1h, the 6-bromo- and 6-(methylsulfonyl)-3',4'-dichlorophenyl analogues, afforded median MIC50 values against 23 rhinovirus serotypes of 0.05 and 0.13 micrograms/mL, respectively. Mice dosed orally with 200 mg/kg of 1c or 1h exhibited serum levels well in excess of each compound's MIC50, indicating that some analogues have the potential to be orally effective drugs.

  DOI：

  10.1021/jm00159a006

文献信息

• 2-phenylpyrano[2,3-b]pyridines and their use in inhibiting viruses
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04588733A1

  公开（公告）日：1986-05-13

  2-Phenylpyrano[2,3-b]pyridines are described herein. These compounds are active against a variety of viruses. A number of procedures can be used to prepare the compounds of this invention but, at some point, they would all make use of the cyclization of a (phenyl) (pyridyl)propanol or (phenyl) (pyridyl)propenol.

  本文描述了2-苯基吡喃并[2,3-b]吡啶。这些化合物对各种病毒具有活性。可以使用多种方法来制备本发明的化合物，但在某个阶段，它们都会利用(苯基)(吡啶基)丙醇或(苯基)(吡啶基)丙烯醇的环化。
• 2-phenylpyrano[2,3-b]pyridines
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0178633A2

  公开（公告）日：1986-04-23

  2-Phenylpyrano [2,3-b]pyridines are described herein. These compounds are active against a variety of viruses. A number of procedures can be used to prepare the compounds of this invention but, at some point, they would all make use of the cyclization of a (phenyl) (pyridyl) propanol or (phenyl) (pyridyl) propenol.

  这里描述的是 2-苯基吡喃并[2,3-b]吡啶。 这些化合物对多种病毒具有活性。 本发明化合物的制备可采用多种方法，但在某些情况下，它们都会利用（苯基）（吡啶基）丙醇或（苯基）（吡啶基）丙烯醇的环化作用。
• Bargar, T. M.; Wilson, T.; Daniel, J. K., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1583 - 1592
  作者：Bargar, T. M.、Wilson, T.、Daniel, J. K.

  DOI：——

  日期：——
• BARGAR, T. M.;WILSON, T.;DANIEL, J. K., J. HETEROCYCL. CHEM., 1985, 22, N 6, 1583-1592
  作者：BARGAR, T. M.、WILSON, T.、DANIEL, J. K.

  DOI：——

  日期：——
• ——
  作者：BARGAR TH. M.、 DANIEL J. K.

  DOI：——

  日期：——