5-氰基苯并呋喃-2-羧酸甲酯 | 84102-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 5-氰基苯并呋喃-2-羧酸甲酯
• 中文别名: 5-氰基苯并呋喃-2-甲酸甲酯
• 英文名称: methyl 5-cyanobenzofuran-2-carboxylate
• 英文别名: methyl 5-cyano-1-benzofuran-2-carboxylate
• CAS: 84102-77-2
• 化学式: C₁₁H₇NO₃
• 分子量: 201.181
• InChiKey: JHRYAFRCGFDTSK-UHFFFAOYSA-N

物化性质

• 沸点：
  338.1±22.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5-氰基苯并呋喃-2-羧酸甲酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以53%的产率得到5-氰基-2-苯并[b]呋喃甲酸
  参考文献：
  名称：

  Use of Conformationally Restricted Benzamidines as Arginine Surrogates in the Design of Platelet GPIIb-IIIa Receptor Antagonists

  摘要：

  The use of 5,6-bicyclic amidines as arginine surrogates in the design of a novel class of potent platelet glycoprotein IIb-IIIa receptor (GPIIb-IIIa) antagonists is described. The additional conformational restriction offered by the bicyclic nucleus results in 20-400-fold increases in potency compared to the freely flexible, acyclic benzamidine counterpart. The design, synthesis, structure-activity relationships (SAR), and in vitro activity of this novel class of GPIIb-IIIa antagonists are presented.

  DOI：

  10.1021/jm970020k
• 作为产物：
  描述：

  (4-溴-2-甲酰基苯氧基)乙酸甲酯 在 盐酸 、 copper(l) iodide 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 5-氰基苯并呋喃-2-羧酸甲酯
  参考文献：
  名称：

  Use of Conformationally Restricted Benzamidines as Arginine Surrogates in the Design of Platelet GPIIb-IIIa Receptor Antagonists

  摘要：

  The use of 5,6-bicyclic amidines as arginine surrogates in the design of a novel class of potent platelet glycoprotein IIb-IIIa receptor (GPIIb-IIIa) antagonists is described. The additional conformational restriction offered by the bicyclic nucleus results in 20-400-fold increases in potency compared to the freely flexible, acyclic benzamidine counterpart. The design, synthesis, structure-activity relationships (SAR), and in vitro activity of this novel class of GPIIb-IIIa antagonists are presented.

  DOI：

  10.1021/jm970020k

文献信息

• Fibrinogen Receptor (GPIIb-IIIa) Antagonists Derived from 5,6-Bicyclic Templates. Amidinoindoles, Amidinoindazoles, and Amidinobenzofurans Containing the <i>N</i>-α-Sulfonamide Carboxylic Acid Function as Potent Platelet Aggregation Inhibitors
  作者：Ting Su、Mary Ann H. Naughton、Mark S. Smyth、Jack W. Rose、Ann E. Arfsten、Jefferson R. McCowan、Joseph A. Jakubowski、Virginia L. Wyss、Kenneth J. Ruterbories、Daniel J. Sall、Robert M. Scarborough

  DOI：10.1021/jm9704863

  日期：1997.12.1

  potent and novel amidinobenzofuran-containing derivatives 46-49. Reexamination of 5,6-bicyclic aromatic nucleus led to the further identification of amidinoindole- and amidinoindazole-containing derivatives 53-55. These analogues, 46-49 and 53-55, exhibited potent in vitro activity with IC50 values of 25-65 nM in platelet aggregation assays and an IC50 value of 2 nM in fibrinogen binding assays and demonstrated

  通过对新型a基吲哚和苯并呋喃化合物Ⅰ和Ⅱ进行结构修饰，发现并优化了一系列高效和特异的纤维蛋白原受体拮抗剂。系统化的接头优化提供了含the基苯并呋喃的抑制剂29，该抑制剂在血小板聚集测定中的IC50值为250 nM。尝试通过修饰29个β-丙氨酰基羧酸酯基团的β-位置来增强活性对聚集分析的抑制活性仅产生适度的影响。还发现为通过构象限制增强活性而制备的类似物具有同等或较弱的效力。相反，在β-丙氨酰基羧酸酯基团的α位上的修饰导致鉴定出非常有效和新颖的含a基苯并呋喃的衍生物46-49。5，6-双环芳香核的重新检查导致进一步鉴定了含a基吲哚和含mid基吲唑的衍生物53-55。这些类似物46-49和53-55表现出强大的体外活性，在血小板凝集试验中的IC50值为25-65 nM，在纤维蛋白原结合试验中的IC50值为2 nM，并且对GPIIb的选择性大于50,000倍-IIIa与最紧密相关的整联蛋白，玻连蛋白受体，αv
• 5,6-Bicyclic glycoprotein IIb IIIa antagonists useful in inhibition of platelet aggregation
  申请人：ELI LILLY AND COMPANY

  公开号：EP0655439A2

  公开（公告）日：1995-05-31

  This invention relates to 5,6 fused ring bicyclic compounds inclusive of indoles, benzofurans, and benzothiophenes, and corresponding to the formula (I) substituted with both basic (B) and acidic (A) functionality, which are useful in inhibition of platelet aggregation.

  本发明涉及包括吲哚、苯并呋喃和苯并噻吩在内的5,6融合环双环化合物，并对应于式(I) 被碱性（B）和酸性（A）官能团取代，可用于抑制血小板聚集。
• Dann, Otto; Char, Helmut; Griessmeier, Helmut, Liebigs Annalen der Chemie, 1982, # 10, p. 1836 - 1869
  作者：Dann, Otto、Char, Helmut、Griessmeier, Helmut

  DOI：——

  日期：——
• Use of Conformationally Restricted Benzamidines as Arginine Surrogates in the Design of Platelet GPIIb-IIIa Receptor Antagonists
  作者：Daniel J. Sall、Ann E. Arfsten、Jolie A. Bastian、Michael L. Denney、Cathy S. Harms、Jefferson R. McCowan、John M. Morin,、Jack W. Rose、Robert M. Scarborough、Mark S. Smyth、Suzane L. Um、Barbara G. Utterback、Robert T. Vasileff、James H. Wikel、Virginia L. Wyss、Joseph A. Jakubowski

  DOI：10.1021/jm970020k

  日期：1997.8.1

  The use of 5,6-bicyclic amidines as arginine surrogates in the design of a novel class of potent platelet glycoprotein IIb-IIIa receptor (GPIIb-IIIa) antagonists is described. The additional conformational restriction offered by the bicyclic nucleus results in 20-400-fold increases in potency compared to the freely flexible, acyclic benzamidine counterpart. The design, synthesis, structure-activity relationships (SAR), and in vitro activity of this novel class of GPIIb-IIIa antagonists are presented.