5-(3-pyridylmethyl)benzofuran-2-carboxylic acid ethyl ester | 85666-16-6

• 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-(3-pyridylmethyl)benzofuran-2-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(3'-pyridinylmethyl)benzofuran-2-carboxylate；Ethyl 5-(3-pyridinylmethyl)-2-benzofurancarboxylate；ethyl 5-(pyridin-3-ylmethyl)-1-benzofuran-2-carboxylate
• CAS: 85666-16-6
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: ULKXOVOWJXGISX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-pyridylmethyl)benzofuran-2-carboxylic acid ethyl ester 在 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 5-<3-(6-chloropyridyl)methyl>-2-benzofurancarboxylic acid ethyl ester
  参考文献：
  名称：

  Thromboxane A2 synthase inhibitors. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acids

  摘要：

  The synthesis and screening of a series of 5-(3-pyridylmethyl)benzofuran-2-carboxylic acids as selective thromboxane A2 (TxA2) synthase inhibitors is outlined. The ability of these compounds to inhibit TxA2 biosynthesis was assayed using microsomal enzyme from human platelets. Substitution of the benzofuran ring caused small changes in potency; modification of the carboxylic acid group caused modest reductions in potency, and substitution of the pyridine ring resulted in large reductions of potency. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acid sodium salt (9b, sodium furegrelate) was chosen for further evaluation as a TxA2 synthase inhibitor.

  DOI：

  10.1021/jm00158a024
• 作为产物：
  描述：

  3-(4'-nitrobenzyl)pyridine 在 palladium on activated charcoal 二环己烷并-18-冠醚-6 、 硫酸 、 水 、 氢气 、 sodium hydride 、 三氟乙酸 、 sodium nitrite 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 54.5h， 生成 5-(3-pyridylmethyl)benzofuran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Thromboxane A2 synthase inhibitors. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acids

  摘要：

  The synthesis and screening of a series of 5-(3-pyridylmethyl)benzofuran-2-carboxylic acids as selective thromboxane A2 (TxA2) synthase inhibitors is outlined. The ability of these compounds to inhibit TxA2 biosynthesis was assayed using microsomal enzyme from human platelets. Substitution of the benzofuran ring caused small changes in potency; modification of the carboxylic acid group caused modest reductions in potency, and substitution of the pyridine ring resulted in large reductions of potency. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acid sodium salt (9b, sodium furegrelate) was chosen for further evaluation as a TxA2 synthase inhibitor.

  DOI：

  10.1021/jm00158a024

文献信息

• Pyridyl-substituted-benzofurans
  申请人：The Upjohn Company

  公开号：US04495357A1

  公开（公告）日：1985-01-22

  The present invention provides novel pyridinyl-benzofurans and derivatives thereof which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and as such represent potent pharmacological agents.

  本发明提供了一种新型吡啶基苯并呋喃及其衍生物，可作为血栓素A.sub.2（TXA.sub.2）合成酶抑制剂，因此代表了强效的药理剂。
• J. Med. Chem. 1986, 29, 1461-1468
  作者：

  DOI：——

  日期：——
• JOHNSON, R. A.
  作者：JOHNSON, R. A.

  DOI：——

  日期：——
• US4495357A
  申请人：——

  公开号：US4495357A

  公开（公告）日：1985-01-22
• Thromboxane A2 synthase inhibitors. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acids
  作者：Roy A. Johnson、Eldon G. Nidy、James W. Aiken、Norman J. Crittenden、Robert R. Gorman

  DOI：10.1021/jm00158a024

  日期：1986.8

  The synthesis and screening of a series of 5-(3-pyridylmethyl)benzofuran-2-carboxylic acids as selective thromboxane A2 (TxA2) synthase inhibitors is outlined. The ability of these compounds to inhibit TxA2 biosynthesis was assayed using microsomal enzyme from human platelets. Substitution of the benzofuran ring caused small changes in potency; modification of the carboxylic acid group caused modest reductions in potency, and substitution of the pyridine ring resulted in large reductions of potency. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acid sodium salt (9b, sodium furegrelate) was chosen for further evaluation as a TxA2 synthase inhibitor.