5-(1-imidazolylmethyl)benzofuran-2-carboxylic acid methyl ester | 82788-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-(1-imidazolylmethyl)benzofuran-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-(imidazol-1-ylmethyl)-1-benzofuran-2-carboxylate
• CAS: 82788-36-1
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: UWLXUPXWOKLGCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(1-imidazolylmethyl)benzofuran-2-carboxylic acid methyl ester 在 氨 作用下， 以 乙醇 为溶剂， 生成 5-(1-imidazolylmethyl)benzofuran-2-carboxamide
  参考文献：
  名称：

  Heterocyclic thromboxane synthetase inhibitors and pharmaceutical

  摘要：

  杂环血栓素合成酶抑制剂的化学式为##STR1##其中R.sup.1，连接到2-、3-或4-位置，是氢、卤素、C.sub.1 -C.sub.4烷基、羟基或C.sub.1 -C.sub.4烷氧基；Y，连接到2-或3-位置，是--COOH、--COO(C.sub.1 -C.sub.4烷基)或--CONH.sub.2；X为O、S、NH、N(C.sub.1 -C.sub.4烷基)或N(苄基)；R，连接到5-、6-或7-位置，是化学式##STR2##或(3-或4-吡啶基)-Z.sup.2-其中Z.sup.1为--CH.sub.2 --、--CH.sub.2 CH.sub.2 --或--CH.sub.2 CH.sub.2 O--，Z.sup.2为--CH.sub.2 --、--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--、--CH.sub.2 O--或--OCH.sub.2 --；以及它们的药学上可接受的盐；它们的制备方法和含有它们的药物组合物。

  公开号：

  US04410539A1
• 作为产物：
  描述：

  5-甲基苯并呋喃-2-羧酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 生成 5-(1-imidazolylmethyl)benzofuran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 3. 1H-Imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene- and indole-2- and 3-carboxylic acids

  摘要：

  The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).

  DOI：

  10.1021/jm00159a012

文献信息

• Heterocyclic thromboxane synthetase inhibitors, processes for their preparation, and pharmaceutical compositions containing them
  申请人：Pfizer Limited

  公开号：EP0050957A1

  公开（公告）日：1982-05-05

  Heterocyclic thromboxane synthetase inhibitors of the formula:- wherein R', which is attached to the 2-, 3- or 4- position, is hydrogen, halogen, C1-C4 alkyl, hydroxy or C1-C4 alkoxy; Y, which is attached to the 2- or 3-position, is -COOH, -COO(C1-C4 alkyl) or-CONH2; X is O, S, NH. N(C1-C4 alkyl) or N(benzyi): and R. which is attached to the 5-, 6- or 7-position, is a group of the formula:- or/3-or 4- pyridyl)-Z2- whereinZ' is.CH2.,-CH2CH2-or-CH2CH2O. and Z2 is-CH2.,-CH2CH2-.-CH=CH--CH2O-or-OCH2-: and their pharmaceutically acceptable satts; processes for their preparation, and pharmaceutical compositions containing them.

  式中的杂环血栓素合成酶抑制剂 其中连接到 2-、3-或 4-位的 R'为氢、卤素、C1-C4 烷基、羟基或 C1-C4 烷氧基； 连接到 2-或 3-位的 Y 是-COOH、-COO（C1-C4 烷基）或-CONH2； X 是 O、S、NHN（C1-C4 烷基）或 N（苄基）： 而连接在 5-、6- 或 7-位的 R.是式中的一个基团：- R. 或/3-或 4-吡啶基）-Z2- 其中Z'是.CH2.,-CH2CH2-或-CH2CH2O.和Z2是-CH2.,-CH2CH2-.-CH=CH--CH2O-或-OCH2-：及其药学上可接受的饱和物；它们的制备工艺和含有它们的药物组合物。
• CROSS P. E.; DICKINSON R. P.; PARRY M. J.; RANDALL M. J., J. MED. CHEM., 1986, 29, N 9, 1637-1643
  作者：CROSS P. E.、 DICKINSON R. P.、 PARRY M. J.、 RANDALL M. J.

  DOI：——

  日期：——
• US4410539A
  申请人：——

  公开号：US4410539A

  公开（公告）日：1983-10-18
• US4551468A
  申请人：——

  公开号：US4551468A

  公开（公告）日：1985-11-05
• Selective thromboxane synthetase inhibitors. 3. 1H-Imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene- and indole-2- and 3-carboxylic acids
  作者：Peter E. Cross、Roger P. Dickinson、M. John Parry、Michael J. Randall

  DOI：10.1021/jm00159a012

  日期：1986.9

  The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).