4-氯-2-碘-3-甲基-噻吩并[2,3-b]吡啶-5-甲腈 | 930293-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 中文名称: 4-氯-2-碘-3-甲基-噻吩并[2,3-b]吡啶-5-甲腈
• 中文别名: 2-碘-3-甲基-4-氯-5-腈基吡啶并噻吩；4-氯-2-碘-3-甲基噻吩并[2,3-B]吡啶-5-氰基
• 英文名称: 4-chloro-2-iodo-3-methylthieno[2,3-b]pyridine-5-carbonitrile
• CAS: 930293-15-5
• 化学式: C₉H₄ClIN₂S
• 分子量: 334.568
• InChiKey: WJBGRENDLJDAAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基-5-氨基吲哚 、 4-氯-2-碘-3-甲基-噻吩并[2,3-b]吡啶-5-甲腈 以 乙醇 为溶剂， 生成 2-Iodo-3-methyl-4-[(4-methyl-1H-indol-5-yl)amino]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
• 作为产物：
  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

文献信息

• Thieno [2,3-B] pyridine-5-carbonitriles as protein kinase inhibitors
  申请人：Boschelli H. Diane

  公开号：US20070082880A1

  公开（公告）日：2007-04-12

  Disclosed are compounds of Formula I: wherein R 1 , R 2 , R 3 , R 4 , and X, are defined hereinbefore in the specification, which can be useful in the treatment of autoimmune and inflammatory diseases, and processes for producing said compounds.

  公开了以下公式I的化合物：其中R1、R2、R3、R4和X在规范中已定义，这些化合物可以用于治疗自身免疫和炎症性疾病，并且公开了生产这些化合物的过程。
• Process for the preparation of 4-hydroxythieno[2,3-b]pyridine-5-carbonitriles
  申请人：Boschelli Harris Diane

  公开号：US20080076926A1

  公开（公告）日：2008-03-27

  A process for the preparation of 4-hydroxythieno[2,3-b]pyridine-5-carbonitriles, which can be useful for the preparation of protein kinase inhibitors, is provided.

  提供一种制备4-羟基噻吩[2,3-b]吡啶-5-碳腈的方法，该方法可用于制备蛋白激酶抑制剂。
• 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.
• THIENO[2,3-B]PYRIDINE-5-CARBONITRILES AS PROTEIN KINASE INHIBITORS
  申请人：Wyeth

  公开号：EP1937690A1

  公开（公告）日：2008-07-02
• PROCESS FOR THE PREPARATION OF 4-HYDROXYTHIENO[2,3-B]PYRIDINE-5-CARBONITRILES
  申请人：Wyeth

  公开号：EP2066675A1

  公开（公告）日：2009-06-10