4-(1H-indol-4-ylamino)-5-[3-(2-methoxyethoxy)phenyl]nicotinonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(1H-indol-4-ylamino)-5-[3-(2-methoxyethoxy)phenyl]nicotinonitrile
• 英文别名: 4-Indolylamino-5-phenyl-3-pyridinecarbonitrile, 7d；4-(1H-indol-4-ylamino)-5-[3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile
• 化学式: C₂₃H₂₀N₄O₂
• 分子量: 384.437
• InChiKey: OVMXFSZIFQUQRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基吲哚 、 4-chloro-5-(3-(2-methoxyethoxy)phenyl)nicotinonitrile 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 乙二醇二甲醚 为溶剂， 生成 4-(1H-indol-4-ylamino)-5-[3-(2-methoxyethoxy)phenyl]nicotinonitrile
  参考文献：
  名称：

  Synthesis and PKCθ inhibitory activity of a series of 4-indolylamino-5-phenyl-3-pyridinecarbonitriles

  摘要：

  A series of 4-indolylamino-5-phenyl-3-pyridinecarbonitrile inhibitors of PKC theta were synthesized as potential anti-inflammatory agents. The effects of specific substitution on the 5-phenyl moiety and variations of the positional isomers of the 4-indolylamino substituent were explored. This study led to the discovery of compound 12d, which had an IC50 value of 18 nM for the inhibition of PKC theta. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.053

文献信息

• Substituted 3-cyanopyridines as protein kinase inhibitors
  申请人：Cole Cecil Derek

  公开号：US20070287708A1

  公开（公告）日：2007-12-13

  The present teachings provide compounds of formula I and their pharmaceutically acceptable salts, hydrates, and esters, wherein R 1 , R 2 , and X are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating autoimmune and inflammatory diseases by administering a therapeutically effective amount of a compound or compounds of formula I to a mammal including a human.

  本发明的教导提供了公式I的化合物及其药用可接受的盐、水合物和酯，其中R1、R2和X如本文所述定义。本发明的教导还提供了制造公式I化合物的方法，以及通过向哺乳动物包括人类施用治疗有效量的公式I化合物或化合物来治疗自身免疫性和炎症性疾病的方法。
• SUBSTITUTED 3-CYANOPYRIDINES AS PROTEIN KINASE INHIBITORS
  申请人：Wyeth

  公开号：EP2029543A2

  公开（公告）日：2009-03-04
• US7781591B2
  申请人：——

  公开号：US7781591B2

  公开（公告）日：2010-08-24
• [EN] SUBSTITUTED 3-CYANOPYRIDINES AS PROTEIN KINASE INHIBITORS<br/>[FR] 3-CYANOPYRIDINES SUBSTITUÉES EN TANT QU'INHIBITEURS DE PROTÉINE KINASES
  申请人：WYETH CORP

  公开号：WO2007146376A2

  公开（公告）日：2007-12-21

  [EN] The present teachings provide compounds of formula I (I) and their pharmaceutically acceptable salts, hydrates, and esters, wherein R¹, R², and X are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating autoimmune and inflammatory diseases by administering a therapeutically effective amount of a compound or compounds of formula I to a mammal including a human.
  [FR] La présente invention concerne des composés représentés par la formule I et leurs sels, hydrates et esters pharmaceutiquement acceptables, formule dans laquelle R¹, R² et X sont tels que définis ici. La présente invention concerne également des procédés de fabrication des composés représentés par la formule I, et des procédés de traitement de maladies auto-immunes et inflammatoires par l'administration d'une quantité thérapeutiquement efficace d'un composé ou de composés représentés par la formule I à un mammifère, y compris à l'humain.
• Synthesis and PKCθ inhibitory activity of a series of 4-indolylamino-5-phenyl-3-pyridinecarbonitriles
  作者：Russell G. Dushin、Thomas Nittoli、Charles Ingalls、Diane H. Boschelli、Derek C. Cole、Allan Wissner、Julie Lee、Xiaoke Yang、Paul Morgan、Agnes Brennan、Divya Chaudhary

  DOI：10.1016/j.bmcl.2009.03.053

  日期：2009.5

  A series of 4-indolylamino-5-phenyl-3-pyridinecarbonitrile inhibitors of PKC theta were synthesized as potential anti-inflammatory agents. The effects of specific substitution on the 5-phenyl moiety and variations of the positional isomers of the 4-indolylamino substituent were explored. This study led to the discovery of compound 12d, which had an IC50 value of 18 nM for the inhibition of PKC theta. (c) 2009 Elsevier Ltd. All rights reserved.