N-<4-fluoro-3-(1H-imidazol-1-ylmethyl)phenyl>-2-pyridinecarbothioamide | 123207-50-1

• 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-(1H-imidazol-1-ylmethyl)phenyl>-2-pyridinecarbothioamide
• 英文别名: N-[4-fluoro-3-[(1H-imidazol-1-yl)methyl]phenyl]-2-pyridinecarbothioamide；N-[4-Fluoro-3-(1H-imidazol-1-ylmethyl)phenyl]-2-pyridinecarbothioamide；N-[4-fluoro-3-(imidazol-1-ylmethyl)phenyl]pyridine-2-carbothioamide
• CAS: 123207-50-1
• 化学式: C₁₆H₁₃FN₄S
• 分子量: 312.37
• InChiKey: SIMWROJHEVKXPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氟-5-硝基苄醇 在 tetraphosphorus decasulfide 、 四溴化碳 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.5h， 生成 N-<4-fluoro-3-(1H-imidazol-1-ylmethyl)phenyl>-2-pyridinecarbothioamide
  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

• 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
• N-Phenyl-2-pyridinecarbothioamides as gastric mucosal protectants
  作者：William A. Kinney、Nancy E. Lee、Robert M. Blank、Christopher A. Demerson、Carol S. Sarnella、Noreen T. Scherer、G. Nabi Mir、Luis E. Borella、John F. DiJoseph、Cheryl Wells

  DOI：10.1021/jm00163a053

  日期：1990.1

  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.