2-iodo-3-methyl-4-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile | 1092655-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 2-iodo-3-methyl-4-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile
• CAS: 1092655-83-8
• 化学式: C₉H₅IN₂OS
• 分子量: 316.122
• InChiKey: DFZJEULJCNJLHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-iodo-3-methyl-4-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile 在 三氯氧磷 作用下， 生成 4-氯-2-碘-3-甲基-噻吩并[2,3-b]吡啶-5-甲腈
  参考文献：
  名称：

  2-Alkenylthieno[2,3-b]pyridine-5-carbonitriles: Potent and selective inhibitors of PKCθ

  摘要：

  A series of 2-alkenyl thieno[2,3-b] pyridine inhibitors of PKC theta were synthesized as potential inflammatory modulators. This series led to the discovery of 2-alkenyl amides, which are exceptionally potent and selective inhibitors of PKC theta. Compound 8 has an IC(50) of 3.8 nM against PKC theta and shows excellent selectivity over a variety of PKC isoforms. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.040
• 作为产物：
  描述：

  3-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 氯仿 为溶剂， 生成 2-iodo-3-methyl-4-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  2-Alkenylthieno[2,3-b]pyridine-5-carbonitriles: Potent and selective inhibitors of PKCθ

  摘要：

  A series of 2-alkenyl thieno[2,3-b] pyridine inhibitors of PKC theta were synthesized as potential inflammatory modulators. This series led to the discovery of 2-alkenyl amides, which are exceptionally potent and selective inhibitors of PKC theta. Compound 8 has an IC(50) of 3.8 nM against PKC theta and shows excellent selectivity over a variety of PKC isoforms. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.040

文献信息

• A facile, scalable preparation of 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles
  作者：L. Nathan Tumey、Niala Bhagirath、Biqi Wu、Diane H. Boschelli

  DOI：10.1016/j.tetlet.2008.09.107

  日期：2008.11

  We report a new synthesis of thieno[2,3-b]pyridine-5-carbonitriles from 2-aminothiophene-3-carboxylate esters. The key step of the synthesis is a thermally promoted elimination/decarboxylation followed by nucleophilic cyclization to give 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles. The reactions proceed in good yield and generally require no chromatographic purification. These compounds are easily transformed in two steps to 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitriles which are key intermediates in the synthesis of various kinase inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.