2-Iodo-4-[(4-methyl-1H-indol-5-yl)amino]thieno[2,3-b]pyridine-5-carbonitrile | 930288-42-9

• 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-4-[(4-methyl-1H-indol-5-yl)amino]thieno[2,3-b]pyridine-5-carbonitrile
• CAS: 930288-42-9
• 化学式: C₁₇H₁₁IN₄S
• 分子量: 430.272
• InChiKey: WBTOBYCVRZKRBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Iodo-4-[(4-methyl-1H-indol-5-yl)amino]thieno[2,3-b]pyridine-5-carbonitrile 在 palladium 10% on activated carbon 氢气 、 sodium acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 4-[(4-methyl-1H-indol-5-yl)amino]thieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Thieno [2,3-B] pyridine-5-carbonitriles as protein kinase inhibitors

  摘要：

  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。

  公开号：

  US20070082880A1
• 作为产物：
  描述：

  4-甲基-5-氨基吲哚 、 4-氯-2-碘噻吩并[2,3-b]吡啶-5-甲腈 以 乙醇 为溶剂， 生成 2-Iodo-4-[(4-methyl-1H-indol-5-yl)amino]thieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and PKCθ inhibitory activity of a series of 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles

  摘要：

  The thieno[2,3-b]pyridine-5-carbonitrile with a 5-indolylamine at C-4 and a phenyl group at C-2 had a moderate activity against PKC theta. Optimization of the groups at C-4 and C-2 led to analog 29, which has an IC50 value of 7.5 nM for the inhibition of PKC theta. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.077

文献信息

• 2-Alkenylthieno[2,3-b]pyridine-5-carbonitriles: Potent and selective inhibitors of PKCθ
  作者：L. Nathan Tumey、Diane H. Boschelli、Julie Lee、Divya Chaudhary

  DOI：10.1016/j.bmcl.2008.06.040

  日期：2008.8

  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.
• Second generation 4-(4-methyl-1H-indol-5-ylamino)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile PKCθ inhibitors
  作者：Biqi Wu、Diane H. Boschelli、Julie Lee、Xiaoke Yang、Divya Chaudhary

  DOI：10.1016/j.bmcl.2008.12.021

  日期：2009.2

  Thieno[2,3-b] pyridine-5-carbonitrile 16 with a 4-methyl-5-indolylamine at C-4 and a 5-methoxy-2-(dimethylamino)-methylphenyl group at C-2 had an IC50 value of 16 nM for the inhibition of PKC theta. While moderate inhibition of PKC delta was also observed (IC50 = 130 nM), 16 had IC50 values of greater than 5 mu M against Lyn and other members of the Src kinase family. (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
• [EN] THIENO[2,3-B]PYRIDINE-5-CARBONITRILES AS PROTEIN KINASE INHIBITORS<br/>[FR] THIÉNO[2,3-B]PYRIDINE-5-CARBONITRILES EN TANT QU'INHIBITEURS DE PROTÉINE KINASES
  申请人：WYETH CORP

  公开号：WO2007038519A1

  公开（公告）日：2007-04-05

  [EN] Disclosed are compounds of Formula I: Formula (I); wherein R¹, R², R³, R⁴ , 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.
  [FR] La présente invention porte sur des composés de Formule I : Formule (I) ; où R¹, R², R³, R⁴ et X sont définis ci-avant dans la description de l'invention, lesdits composés pouvant être employés dans le traitement de maladies auto-immunes et inflammatoires ; la présente invention porte également sur des procédés de synthèse desdits composés.