(E)-5-Bromo-α-(2-phenylethenyl)-2-methoxy-3-pyridinemethanol | 102830-77-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-5-Bromo-α-(2-phenylethenyl)-2-methoxy-3-pyridinemethanol
• 英文别名: (E)-1-(5-bromo-2-methoxypyridin-3-yl)-3-phenylprop-2-en-1-ol
• CAS: 102830-77-3
• 化学式: C₁₅H₁₄BrNO₂
• 分子量: 320.186
• InChiKey: NNJHWFACGYVGPT-BQYQJAHWSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  466.6±45.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-Bromo-α-(2-phenylethenyl)-2-methoxy-3-pyridinemethanol 在 W-2 Raney Ni 氢溴酸 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.25h， 生成 6-Brono-3,4-dihydro-2-phenyl-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 、 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 22.25h， 生成 (E)-5-Bromo-α-(2-phenylethenyl)-2-methoxy-3-pyridinemethanol
  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
  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：——
• US4588733A
  申请人：——

  公开号：US4588733A

  公开（公告）日：1986-05-13
• 3,4-Dihydro-2-phenyl-2H-pyrano[2,3-b]pyridines with potent antirhinovirus activity
  作者：Thomas M. Bargar、Jacqueline K. Dulworth、Michael T. Kenny、Renee Massad、John K. Daniel、Thomas Wilson、Roger N. Sargent

  DOI：10.1021/jm00159a006

  日期：1986.9

  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.