5-(4-carboxy-1,3-butadienyl)imidazo<1,5-a>pyridine | 85691-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5-(4-carboxy-1,3-butadienyl)imidazo<1,5-a>pyridine
• 英文别名: 5-(4-Carboxybuta-1,3-dienyl)-imidazo[1,5-a]pyridine；5-imidazo[1,5-a]pyridin-5-ylpenta-2,4-dienoic acid
• CAS: 85691-69-6
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: GHENEUQHDIPOPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  咪唑并[1,5-a]吡啶-5-甲醛 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 19.0h， 生成 5-(4-carboxy-1,3-butadienyl)imidazo<1,5-a>pyridine
  参考文献：
  名称：

  Imidazo[1,5-a]pyridines: a new class of thromboxane A2 synthetase inhibitors

  摘要：

  The synthesis and structure-activity profile of a new class of potent and highly specific thromboxane A2 synthetase inhibitors is described. The most potent member of this series in vitro is determined to be imidazo[1,5-a]-pyridine-5-hexanoic acid (9).

  DOI：

  10.1021/jm00380a003

文献信息

• Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane
  申请人：Ciba-Geigy Corporation

  公开号：US04588732A1

  公开（公告）日：1986-05-13

  Disclosed are compounds of the formula I ##STR1## or a 5,6,7,8-tetrahydro derivative thereof, wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, or aryl-lower alkoxy in which aryl represents phenyl or phenyl substituted by lower alkoxy, lower alkyl, halogen or trifluoromethyl; R.sub.2 represents hydrogen, halogen, or lower alkyl; C represents carboxy, lower alkoxycarbonyl, unsubstituted or mono- or di-(lower alkyl) substituted carbamoyl, cyano, formyl, hydroxymethyl, 5-tetrazolyl, dihydro-2-oxazolyl, dihydro-2-oxazolyl substituted by lower alkyl, or hydroxycarbamoyl; and (a) A represents ethenylene or ethenylene substituted by lower alkyl; B is straight chain or branched alkylene of 1 to 12 carbon atoms, alkynylene or alkenylene of 2 to 12 carbon atoms, phenylene-lower alkylene, phenylene-lower alkenylene, phenylene, or phenylene-(thio or oxy)-lower alkylene; or (b) A represents a direct bond; B represents lower alkylenephenylene, phenylene lower alkylene, phenylene, lower alkylene-(thio or oxy)-lower alkylene, lower alkylene-(thio or oxy)-phenylene, phenylene-(thio or oxy)-lower alkylene, phenylene-lower alkenylene, lower alkylenephenylene-lower alkenylene, or straight chain or branched alkadienylene of 5 to 12 carbon atoms; or a pharmaceutically acceptable salt thereof; and methods of synthesis thereof. Said compounds are useful as selective thromboxane synthetase inhibitors for the treatment of diseases such as cerebral ischaemia, shock, thrombosis and ischaemic heart disease.

  本发明涉及式I的化合物 ##STR1## 或其5,6,7,8-四氢衍生物，其中R.sub.1为氢、卤素、低烷基、低烷氧基、羟基或芳基-低烷氧基，其中芳基代表苯基或被低烷氧基、低烷基、卤素或三氟甲基取代的苯基；R.sub.2代表氢、卤素或低烷基；C代表羧基、低烷氧羰基、未取代或单烷基或二烷基取代的氨基甲酰基、氰基、甲酰基、羟甲基、5-四唑基、二氢-2-噁唑基、被低烷基取代的二氢-2-噁唑基或羟基氨基甲酰基；以及（a）A代表乙烯基或被低烷基取代的乙烯基；B为直链或支链1至12个碳原子的烷基、2至12个碳原子的炔基或烯基、苯基-低烷基、苯基-低烯基、苯基或苯基-(硫或氧)-低烷基；或（b）A代表直接键；B代表低烷基烷基苯、苯基-低烷基、苯基、低烷基-(硫或氧)-低烷基、低烷基-(硫或氧)-苯基、苯基-(硫或氧)-低烷基、苯基-低烯基、低烷基烷基苯-低烯基或直链或支链5至12个碳原子的烯烃基；或其药学上可接受的盐；以及其合成方法。所述化合物可用作选择性血栓素合酶抑制剂，用于治疗脑缺血、休克、血栓形成和缺血性心脏病等疾病。
• Imidazo[1,5-a]pyridines: a new class of thromboxane A2 synthetase inhibitors
  作者：Neville F. Ford、Leslie J. Browne、Thomas Campbell、Charles Gemenden、Robert Goldstein、Candido Gude、Jan W. F. Wasley

  DOI：10.1021/jm00380a003

  日期：1985.2

  The synthesis and structure-activity profile of a new class of potent and highly specific thromboxane A2 synthetase inhibitors is described. The most potent member of this series in vitro is determined to be imidazo[1,5-a]-pyridine-5-hexanoic acid (9).