N-[4-(cyclohexylamino)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-5-yl]acetamide | 1421338-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-(cyclohexylamino)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-5-yl]acetamide
• CAS: 1421338-18-2
• 化学式: C₂₂H₂₆N₄O₃S
• 分子量: 426.539
• InChiKey: GFNHSQGWZGMWCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(cyclohexylamino)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-5-yl]acetamide 在 sodium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 生成 1-cyclohexyl-2-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Design and synthesis of tricyclic cores for kinase inhibition

  摘要：

  Interest in therapeutic kinase inhibitors continues to grow beyond success in oncology. To date, ATP-mimetic kinase inhibitors have focused primarily on monocyclic and bicyclic heterocyclic cores. We sought to expand on the repertoire of potential cores for kinase inhibition by exploring tricyclic variants of classical bicyclic hinge binding motifs such as pyrrolopyridine and pyrrolopyrazine. Herein we describe the syntheses of eight alternative tricyclic cores as well as in vitro screening results for representative kinases of potential therapeutic interest. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.108
• 作为产物：
  描述：

  4-chloro-5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridine 在 tin(II) chloride dihdyrate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 N-[4-(cyclohexylamino)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-5-yl]acetamide
  参考文献：
  名称：

  Design and synthesis of tricyclic cores for kinase inhibition

  摘要：

  Interest in therapeutic kinase inhibitors continues to grow beyond success in oncology. To date, ATP-mimetic kinase inhibitors have focused primarily on monocyclic and bicyclic heterocyclic cores. We sought to expand on the repertoire of potential cores for kinase inhibition by exploring tricyclic variants of classical bicyclic hinge binding motifs such as pyrrolopyridine and pyrrolopyrazine. Herein we describe the syntheses of eight alternative tricyclic cores as well as in vitro screening results for representative kinases of potential therapeutic interest. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.108

文献信息

• Design and synthesis of tricyclic cores for kinase inhibition
  作者：Stacy Van Epps、Bryan Fiamengo、Jeremy Edmunds、Anna Ericsson、Kristine Frank、Michael Friedman、Dawn George、Jonathan George、Eric Goedken、Brian Kotecki、Gloria Martinez、Philip Merta、Michael Morytko、Shashank Shekhar、Barbara Skinner、Kent Stewart、Jeffrey Voss、Grier Wallace、Lu Wang、Lu Wang、Neil Wishart

  DOI：10.1016/j.bmcl.2012.11.108

  日期：2013.2

  Interest in therapeutic kinase inhibitors continues to grow beyond success in oncology. To date, ATP-mimetic kinase inhibitors have focused primarily on monocyclic and bicyclic heterocyclic cores. We sought to expand on the repertoire of potential cores for kinase inhibition by exploring tricyclic variants of classical bicyclic hinge binding motifs such as pyrrolopyridine and pyrrolopyrazine. Herein we describe the syntheses of eight alternative tricyclic cores as well as in vitro screening results for representative kinases of potential therapeutic interest. (c) 2012 Elsevier Ltd. All rights reserved.