N-<4-fluoro-3-(hydroxymethyl)phenyl>-2-pyridinecarboxamide | 123207-52-3

• 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: N-<4-fluoro-3-(hydroxymethyl)phenyl>-2-pyridinecarboxamide
• 英文别名: N-(4-fluoro-3-hydroxymethylphenyl)-2-pyridinecarboxamide；N-[4-fluoro-3-(hydroxymethyl)phenyl]pyridine-2-carboxamide
• CAS: 123207-52-3
• 化学式: C₁₃H₁₁FN₂O₂
• 分子量: 246.241
• InChiKey: UOMPCUWIEHEBPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 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：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<4-fluoro-3-(hydroxymethyl)phenyl>-2-pyridinecarboxamide 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到N-<3-bromomethyl)-4-fluorophenyl>-2-pyridinecarboxamide
  参考文献：
  名称：

  N-Phenyl-2-pyridinecarbothioamides as gastric mucosal protectants

  摘要：

  A series of substituted 2-pyridinecarbothioamides was synthesized and evaluated for gastric mucosal protectant activity in the rat. Out of this investigation N-(3,5-difluorophenyl)-2- pyridinecarbothioamide (23, AY-31,574) was identified. This compound was much more potent than sucralfate and ranitidine against ethanol-induced lesions. Compound 23 was equipotent with ranitidine against gastric injury caused by stress. Unlike ranitidine, 23 was found to be devoid of antisecretory activity in the pylorus-ligated rat model, making it a selective mucosal protectant. Such a potent selective mucosal protectant may provide a novel clinical approach in treating ulcers.

  DOI：

  10.1021/jm00163a053
• 作为产物：
  描述：

  2-氟-5-硝基苄醇 在 potassium carbonate 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 75.5h， 生成 N-<4-fluoro-3-(hydroxymethyl)phenyl>-2-pyridinecarboxamide
  参考文献：
  名称：

  N-Phenyl-2-pyridinecarbothioamides as gastric mucosal protectants

  摘要：

  A series of substituted 2-pyridinecarbothioamides was synthesized and evaluated for gastric mucosal protectant activity in the rat. Out of this investigation N-(3,5-difluorophenyl)-2- pyridinecarbothioamide (23, AY-31,574) was identified. This compound was much more potent than sucralfate and ranitidine against ethanol-induced lesions. Compound 23 was equipotent with ranitidine against gastric injury caused by stress. Unlike ranitidine, 23 was found to be devoid of antisecretory activity in the pylorus-ligated rat model, making it a selective mucosal protectant. Such a potent selective mucosal protectant may provide a novel clinical approach in treating ulcers.

  DOI：

  10.1021/jm00163a053

文献信息

• 2-pyridinecarbothioamides, processes for preparation thereof and
  申请人：American Home Products Corporation

  公开号：US04958023A1

  公开（公告）日：1990-09-18

  There are provided gastric antiulcer and cytoprotective substituted N-phenyl-2-pyridinecarbothioamides. The process for their production and formulation is disclosed.

  提供了胃抗溃疡和细胞保护的取代N-苯基-2-吡啶羧硫脲。公开了它们的生产和配方过程。
• 2-Pyridinecarbothioamides and pharmaceutical compositions comprising the
  申请人：American Home Products Corporation

  公开号：US04873238A1

  公开（公告）日：1989-10-10

  There are provided gastric antiulcer and cytoprotective substituted N-phenyl-2-pyridinecarbothioamides. The process for their production and formulation is disclosed.

  提供了胃抗溃疡和细胞保护的取代的N-苯基-2-吡啶羧硫酰胺。公开了它们的生产和配方过程。
• KINNEY, WILLIAM A.;LEE, NANCY E.;BLANK, ROBERT M.;DEMERSON, CHRISTOPHER A+, J. MED. CHEM., 33,(1990) N, C. 327-336
  作者：KINNEY, WILLIAM A.、LEE, NANCY E.、BLANK, ROBERT M.、DEMERSON, CHRISTOPHER A+

  DOI：——

  日期：——
• US4873238A
  申请人：——

  公开号：US4873238A

  公开（公告）日：1989-10-10
• US4958023A
  申请人：——

  公开号：US4958023A

  公开（公告）日：1990-09-18