2-bromo-4'-(4-pyridyl)acetophenone hydrobromide | 137103-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-4'-(4-pyridyl)acetophenone hydrobromide
• 英文别名: 2-Bromo-1-(4-pyridin-4-ylphenyl)ethanone;hydrobromide；2-bromo-1-(4-pyridin-4-ylphenyl)ethanone;hydrobromide
• CAS: 137103-79-8
• 化学式: BrH*C₁₃H₁₀BrNO
• 分子量: 357.044
• InChiKey: WUJQWXDMCDWIJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4'-(4-pyridyl)acetophenone hydrobromide 在 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 生成 1-(4-trifluoromethylphenyl)-1-[4-(4-pyridyl)phenyl]-2-(1-imidazolyl)ethanol
  参考文献：
  名称：

  Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols are described. These compounds show potent dose-dependent topical antiinflammatory activity in murine models of skin inflammation. This effect is likely due to inhibition of cytochrome P450 and consequent reduction in levels of 12R-HETE in the skin. These compounds were examined for their ability to inhibit the oxidative metabolism of arachidonic acid; they specifically inhibit the formation of prostacyclins in mouse macrophages. To study the effects of structure on the in vivo activity, three general features of the molecules were varied: the position of attachment of the pyridine nucleus (A), the second aromatic residue (B), and the nitrogen base on the ethanol chain (C). 1-[4-(4-Pyridyl)phenyl]-1-(4-fluorophenyl)-2-imidazolylethanol (2a, DuP 983) shows a very attractive profile of antiinflammatory activity and has been selected for clinical evaluation as a topical antiinflammatory agent.

  DOI：

  10.1021/jm00095a009
• 作为产物：
  描述：

  1-(4-(吡啶-4-基)苯基)乙烷-1-酮 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 以97%的产率得到2-bromo-4'-(4-pyridyl)acetophenone hydrobromide
  参考文献：
  名称：

  Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols are described. These compounds show potent dose-dependent topical antiinflammatory activity in murine models of skin inflammation. This effect is likely due to inhibition of cytochrome P450 and consequent reduction in levels of 12R-HETE in the skin. These compounds were examined for their ability to inhibit the oxidative metabolism of arachidonic acid; they specifically inhibit the formation of prostacyclins in mouse macrophages. To study the effects of structure on the in vivo activity, three general features of the molecules were varied: the position of attachment of the pyridine nucleus (A), the second aromatic residue (B), and the nitrogen base on the ethanol chain (C). 1-[4-(4-Pyridyl)phenyl]-1-(4-fluorophenyl)-2-imidazolylethanol (2a, DuP 983) shows a very attractive profile of antiinflammatory activity and has been selected for clinical evaluation as a topical antiinflammatory agent.

  DOI：

  10.1021/jm00095a009

文献信息

• PYRIDYLPHENYL NITROGEN HETEROCYCLE-SUBSTITUTED CARBINOLS AND DERIVATIVES THEREOF WITH ANTI-INFLAMMATORY ACTIVITY
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0513149A1

  公开（公告）日：1992-11-19
• US5049570A
  申请人：——

  公开号：US5049570A

  公开（公告）日：1991-09-17
• [EN] PYRIDYLPHENYL NITROGEN HETEROCYCLE-SUBSTITUTED CARBINOLS AND DERIVATIVES THEREOF WITH ANTI-INFLAMMATORY ACTIVITY
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1991011445A1

  公开（公告）日：1991-08-08

  (EN) Pyridylphenyl nitrogen heterocycle-substituted carbinols and derivatives thereof and pharmaceutical compositions containing such compounds are useful for treating inflammatory diseases in mammals.(FR) Des carbinols à substitution hétérocyclique d'azote de pyridylphényle ainsi que leurs dérivés et des compositions pharmaceutiques contenant lesdits composés, sont utiles dans le traitement de maladies inflammatoires chez les mammifères.
• Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity
  作者：Stephen W. Wright、Richard R. Harris、Robert J. Collins、Ronald L. Corbett、Alicia M. Green、Eric A. Wadman、Douglas G. Batt

  DOI：10.1021/jm00095a009

  日期：1992.8

  The synthesis, biological evaluation, and structure-activity relationships of a series of 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols are described. These compounds show potent dose-dependent topical antiinflammatory activity in murine models of skin inflammation. This effect is likely due to inhibition of cytochrome P450 and consequent reduction in levels of 12R-HETE in the skin. These compounds were examined for their ability to inhibit the oxidative metabolism of arachidonic acid; they specifically inhibit the formation of prostacyclins in mouse macrophages. To study the effects of structure on the in vivo activity, three general features of the molecules were varied: the position of attachment of the pyridine nucleus (A), the second aromatic residue (B), and the nitrogen base on the ethanol chain (C). 1-[4-(4-Pyridyl)phenyl]-1-(4-fluorophenyl)-2-imidazolylethanol (2a, DuP 983) shows a very attractive profile of antiinflammatory activity and has been selected for clinical evaluation as a topical antiinflammatory agent.