1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-1-ethanol | 137103-81-2

• 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: 1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-1-ethanol
• 英文别名: 1-(4-fluorophenyl)-1-[4-(4-pyridyl)phenyl]ethanol；1-(4-fluorophenyl)-1-[4-(pyridin-4-yl)phenyl]ethanol；1-(4-fluorophenyl)-1-(4-pyridin-4-ylphenyl)ethanol
• CAS: 137103-81-2
• 化学式: C₁₉H₁₆FNO
• 分子量: 293.341
• InChiKey: OHLVLRXFSBTSNM-UHFFFAOYSA-N

物化性质

• 沸点：
  441.6±40.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-1-ethanol 在 吡啶 、 四氧化锇 、 potassium tert-butylate 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 58.5h， 生成 1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-2-(1-imidazolyl)-1-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：

  4-溴吡啶 在 盐酸 、 bis(triphenylphosphine)nickel(II) chloride 、 正丁基锂 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-1-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

文献信息

• Pyridylphenyl nitrogen heterocycle-substituted carbinols and derivatives
  申请人：Du Pont Merck Pharmaceutical Company

  公开号：US05049570A1

  公开（公告）日：1991-09-17

  Pyridylphenyl nitrogen heterocycle-substituted carbinols and derivatives thereof and pharmaceutical compositions containing such compounds are useful for treating inflammatory diseases in mammals.

  吡啶基苯基氮杂环取代的羟甲基化合物及其衍生物，以及含有这些化合物的药物组合物，可用于治疗哺乳动物的炎症性疾病。
• PYRIDYLPHENYL NITROGEN HETEROCYCLE-SUBSTITUTED CARBINOLS AND DERIVATIVES THEREOF WITH ANTI-INFLAMMATORY ACTIVITY
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0513149B1

  公开（公告）日：1995-12-13
• 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.