4-[(4-methyl-1H-indol-5-yl)amino]-5-vinylnicotinonitrile | 1160918-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[(4-methyl-1H-indol-5-yl)amino]-5-vinylnicotinonitrile
• 英文别名: 5-ethenyl-4-[(4-methyl-1H-indol-5-yl)amino]pyridine-3-carbonitrile
• CAS: 1160918-11-5
• 化学式: C₁₇H₁₄N₄
• 分子量: 274.325
• InChiKey: LBPFQPNAUVOEQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(4-methyl-1H-indol-5-yl)amino]-5-vinylnicotinonitrile 、 4-Bromo-N,N-diisopropyl-benzenesulfonamide 在 palladium diacetate 、 三乙胺 、 三对苯甲基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[2-[5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl]ethenyl]-N,N-di(propan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and PKCθ inhibitory activity of a series of 5-vinyl phenyl sulfonamide-3-pyridinecarbonitriles

  摘要：

  A series of 5-vinyl phenyl sulfonamide-3-pyridinecarbonitriles were prepared and evaluated as PKC theta inhibitors. Optimization resulted in the identification of compound 15 with an IC(50) value 0.44 nM for the inhibition of PKC theta with 150-fold selectivity over PKC delta. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.031
• 作为产物：
  描述：

  5-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile 、 三丁基乙烯基锡 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-[(4-methyl-1H-indol-5-yl)amino]-5-vinylnicotinonitrile
  参考文献：
  名称：

  First generation 5-vinyl-3-pyridinecarbonitrile PKCθ inhibitors

  摘要：

  A series of 5-vinyl-3-pyridinecarbonitriles were synthesized and evaluated as PKC theta inhibitors. The systematic optimization of 4-[(4-methyl-1H-indol-5-yl)amino]-5-[(E)-2-phenylvinyl]-3-pyridinecarbonitrile 3 resulted in the identification of compound 23e as a potent PKC theta inhibitor with good selectivity over PKC delta. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.086

文献信息

• [EN] 5-ALKYL/ALKENYL-3-CYANOPYRIDINES AS KINASE INHIBITORS<br/>[FR] 5-ALKYL/ALCÉNYL-3-CYANOPYRIDINES EN TANT QU'INHIBITEURS DE KINASE
  申请人：WYETH CORP

  公开号：WO2009076602A8

  公开（公告）日：2010-02-18
• Optimization of 5-vinylaryl-3-pyridinecarbonitriles as PKCθ inhibitors
  作者：Diane H. Boschelli、Joan Subrath、Chuansheng Niu、Biqi Wu、Yan Wang、Julie Lee、Agnes Brennan、Melisa Ho、Bijia Deng、Xiaoke Yang、Xin Xu、Louis Leung、Jianyao Wang、James Atherton、Divya Chaudhary

  DOI：10.1016/j.bmcl.2010.01.119

  日期：2010.3

  Analog 8, a 3-pyridinecarbonitrile with an (E)-2-6-[(4-methylpiperazin-1-yl) methyl]pyridin-2-yl} vinyl group at C-5, had an IC(50) value of 1.1 nM for the inhibition of PKC theta and potently blocked the production of IL-2 in both stimulated murine T cells (IC(50) = 34 nM) and human whole blood (IC(50) = 500 nM). (C) 2010 Elsevier Ltd. All rights reserved.
• 5-ALKYL/ALKENYL-3-CYANOPYRIDINES AS KINASE INHIBITORS
  申请人：Wyeth LLC

  公开号：EP2229377A1

  公开（公告）日：2010-09-22