6-Chloro-2-ethylamino-3-nitro-benzonitrile | 870486-43-4

• 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: 6-Chloro-2-ethylamino-3-nitro-benzonitrile
• 英文别名: 6-chloro-2-(ethylamino)-3-nitrobenzonitrile
• CAS: 870486-43-4
• 化学式: C₉H₈ClN₃O₂
• 分子量: 225.634
• InChiKey: NSAXHHDATPGCAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Chloro-2-ethylamino-3-nitro-benzonitrile 在 palladium on activated charcoal 硫酸 、 potassium tert-butylate 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 20.0~100.0 ℃ 、344.74 kPa 条件下， 反应 32.5h， 生成 2-(2,6-Dichloro-phenylamino)-1-ethyl-6,7-dimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one
  参考文献：
  名称：

  Optimization of 2-Phenylaminoimidazo[4,5-h]isoquinolin-9-ones:  Orally Active Inhibitors of lck Kinase

  摘要：

  The tyrosine kinase p56lck (lck) is essential for T cell activation; thus, inhibitors of lck have potential utility as autoimmune agents. Our initial disclosure of a new class of lck inhibitors based on the phenylaminoimidazoisoquinolin-9-one showed reasonable cellular activity but did not work in vivo upon oral administration. Our current work highlights the further use of rational drug design and molecular modeling to produce a series of lck inhibitors that demonstrate cellular activity below 100 nM and are as efficacious as cyclosporin A in an in vivo mouse model of anti-CD3-induced IL-2 production.

  DOI：

  10.1021/jm020446l
• 作为产物：
  描述：

  2,6-二氯-3-硝基苯肼 、 乙胺 以 四氢呋喃 为溶剂， 生成 6-Chloro-2-ethylamino-3-nitro-benzonitrile
  参考文献：
  名称：

  苯并咪唑衍生物作为二肽基肽酶IV抑制剂的基于结构的设计和合成。

  摘要：

  使用基于结构的药物设计，从一个小片段击中，开发了一系列新型的非共价，基于苯并咪唑的DPP-4抑制剂。为SAR的发展创造了一种高度通用的合成途径，这导致发现了具有出色药物特性的有效和选择性抑制剂。

  DOI：

  10.1016/j.bmcl.2008.02.071

文献信息

• Dipeptidyl peptidase inhibitors
  申请人：Feng Jun

  公开号：US20050272765A1

  公开（公告）日：2005-12-08

  Compounds, pharmaceutical compositions, kits and methods are provided for use with DPP-IV and other S9 proteases that comprise a compound of the formula: wherein the substituents are as defined herein.

  提供了用于与DPP-IV和其他S9蛋白酶一起使用的化合物、药物组合物、试剂盒和方法，其中包括以下式子的化合物：其中取代基如本文所定义。
• DIPEPTIDYL PEPTIDASE INHIBITORS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1753730A1

  公开（公告）日：2007-02-21
• US7687638B2
  申请人：——

  公开号：US7687638B2

  公开（公告）日：2010-03-30
• [EN] DIPEPTIDYL PEPTIDASE INHIBITORS<br/>[FR] INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE
  申请人：TAKEDA SAN DIEGO INC

  公开号：WO2005118555A1

  公开（公告）日：2005-12-15

  Compounds, pharmaceutical compositions, kits and methods are provided for use with DPP-IV and other S9 proteases that comprise a compound of the formula (I): wherein the substituents are as defined herein.
• Optimization of 2-Phenylaminoimidazo[4,5-<i>h</i>]isoquinolin-9-ones:  Orally Active Inhibitors of lck Kinase
  作者：Daniel R. Goldberg、Tanja Butz、Mario G. Cardozo、Robert J. Eckner、Abdelhakim Hammach、Jessica Huang、Scott Jakes、Suresh Kapadia、Mohammed Kashem、Susan Lukas、Tina M. Morwick、Maret Panzenbeck、Usha Patel、Susan Pav、Gregory W. Peet、Jeffrey D. Peterson、Anthony S. Prokopowicz、Roger J. Snow、Rosemarie Sellati、Hidenori Takahashi、Jonathan Tan、Matt A. Tschantz、Xiao-Jun Wang、Yong Wang、John Wolak、Pla Xiong、Neil Moss

  DOI：10.1021/jm020446l

  日期：2003.4.1

  The tyrosine kinase p56lck (lck) is essential for T cell activation; thus, inhibitors of lck have potential utility as autoimmune agents. Our initial disclosure of a new class of lck inhibitors based on the phenylaminoimidazoisoquinolin-9-one showed reasonable cellular activity but did not work in vivo upon oral administration. Our current work highlights the further use of rational drug design and molecular modeling to produce a series of lck inhibitors that demonstrate cellular activity below 100 nM and are as efficacious as cyclosporin A in an in vivo mouse model of anti-CD3-induced IL-2 production.