2,6-bis(3-cyanophenoxy)pyridine-3-carboxylic acid, ethyl ester | 183306-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis(3-cyanophenoxy)pyridine-3-carboxylic acid, ethyl ester
• 英文别名: Ethyl 2,6-bis(3-cyanophenoxy)pyridine-3-carboxylate
• CAS: 183306-74-3
• 化学式: C₂₂H₁₅N₃O₄
• 分子量: 385.379
• InChiKey: APORXUURFBHFMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-bis(3-cyanophenoxy)pyridine-3-carboxylic acid, ethyl ester 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 2,6-bis(3-amidinophenoxy)-pyridine-3-carboxylic acid, ethyl ester
  参考文献：
  名称：

  Design, Synthesis, and Activity of 2,6-Diphenoxypyridine-Derived Factor Xa Inhibitors

  摘要：

  A novel series of 2,6-diphenoxypyridines has been designed to inhibit factor Xa, a serine protease strategically located in the coagulation cascade. The evolution from the photochemically unstable bisamidine (Z,Z)-BABCH to potent bisamidine compounds with a pyridine heterocycle as the core scaffold has been achieved. The most potent compound in the series, 6h, has a K-i for human factor Xa of 12 nM. The selectivity of 6h against bovine trypsin and human thrombin was greater than 90- and 1000-fold, respectively. Two proposed modes of binding of 6h Do factor Xa are made based on the crystal structures of 6h by itself and of 6h bound to bovine trypsin.

  DOI：

  10.1021/jm980667k
• 作为产物：
  描述：

  2,6-difluoropyridine 、 3-氰基苯酚 生成 2,6-bis(3-cyanophenoxy)pyridine-3-carboxylic acid, ethyl ester
  参考文献：
  名称：

  Benzamidine derivatives and their use as anti-coagulants

  摘要：

  这项发明涉及对苯甲酰胺衍生物的研究，这些衍生物可用作抗凝剂。该发明还涉及含有该发明中化合物的药物组合物，以及使用这些化合物治疗由血栓活动特征的疾病状态的方法。

  公开号：

  US06350746B1

文献信息

• Benzamidine derivatives and their use as anti-coagulants
  申请人：Berlex Laboratories, Inc.

  公开号：US06350746B1

  公开（公告）日：2002-02-26

  This invention is directed to benzamidine derivatives which are useful as anti-coagulants. This invention is also directed to pharmaceutical compositions containing the compounds of the invention, and methods of using the compounds to treat disease-states characterized by thrombotic activity.

  这项发明涉及对苯甲酰胺衍生物的研究，这些衍生物可用作抗凝剂。该发明还涉及含有该发明中化合物的药物组合物，以及使用这些化合物治疗由血栓活动特征的疾病状态的方法。
• Design, Synthesis, and Activity of 2,6-Diphenoxypyridine-Derived Factor Xa Inhibitors
  作者：Gary Phillips、David D. Davey、Keith A. Eagen、Sunil K. Koovakkat、Amy Liang、Howard P. Ng、Michael Pinkerton、Lan Trinh、Marc Whitlow、Alicia M. Beatty、Michael M. Morrissey

  DOI：10.1021/jm980667k

  日期：1999.5.1

  A novel series of 2,6-diphenoxypyridines has been designed to inhibit factor Xa, a serine protease strategically located in the coagulation cascade. The evolution from the photochemically unstable bisamidine (Z,Z)-BABCH to potent bisamidine compounds with a pyridine heterocycle as the core scaffold has been achieved. The most potent compound in the series, 6h, has a K-i for human factor Xa of 12 nM. The selectivity of 6h against bovine trypsin and human thrombin was greater than 90- and 1000-fold, respectively. Two proposed modes of binding of 6h Do factor Xa are made based on the crystal structures of 6h by itself and of 6h bound to bovine trypsin.