(Z)-tert-butyl-3-bromo-4-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-cyanophenylcarbamate

• 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: (Z)-tert-butyl-3-bromo-4-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-cyanophenylcarbamate
• 英文别名: tert-butyl N-[3-bromo-4-[(4-chlorodithiazol-5-ylidene)amino]-2-cyanophenyl]carbamate
• 化学式: C₁₄H₁₂BrClN₄O₂S₂
• 分子量: 447.764
• InChiKey: CKBVVUIUYSDESZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-tert-butyl-3-bromo-4-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-cyanophenylcarbamate 在 copper(l) iodide 、 溶剂黄146 作用下， 以 吡啶 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.19h， 生成 9-(2,4-dichlorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile
  参考文献：
  名称：

  An Unusual Binding Model of the Methyl 9-Anilinothiazolo[5,4-f] quinazoline-2-carbimidates (EHT 1610 and EHT 5372) Confers High Selectivity for Dual-Specificity Tyrosine Phosphorylation-Regulated Kinases

  摘要：

  Methyl 9-anilinothiazolo[5,4-f]quinazoline-2-carbimidates 1 (EHT 5372) and 2 (EHT 1610) are strong inhibitors of DYRK's family kinases. The crystal structures of the complex revealed a noncanonical binding mode of compounds I and 2 in DYRK2, explaining the remarkable selectivity and potency of these inhibitors. The structural data and comparison presented here provide therefore a template for further improvement of this inhibitor class and for the development of novel inhibitors selectively targeting DYRK kinases.

  DOI：

  10.1021/acs.jmedchem.6b01083
• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 吡啶 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 溴 、 甲酸铵 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (Z)-tert-butyl-3-bromo-4-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-cyanophenylcarbamate
  参考文献：
  名称：

  An Unusual Binding Model of the Methyl 9-Anilinothiazolo[5,4-f] quinazoline-2-carbimidates (EHT 1610 and EHT 5372) Confers High Selectivity for Dual-Specificity Tyrosine Phosphorylation-Regulated Kinases

  摘要：

  Methyl 9-anilinothiazolo[5,4-f]quinazoline-2-carbimidates 1 (EHT 5372) and 2 (EHT 1610) are strong inhibitors of DYRK's family kinases. The crystal structures of the complex revealed a noncanonical binding mode of compounds I and 2 in DYRK2, explaining the remarkable selectivity and potency of these inhibitors. The structural data and comparison presented here provide therefore a template for further improvement of this inhibitor class and for the development of novel inhibitors selectively targeting DYRK kinases.

  DOI：

  10.1021/acs.jmedchem.6b01083

文献信息

• An Unusual Binding Model of the Methyl 9-Anilinothiazolo[5,4-<i>f</i>] quinazoline-2-carbimidates (EHT 1610 and EHT 5372) Confers High Selectivity for Dual-Specificity Tyrosine Phosphorylation-Regulated Kinases
  作者：Apirat Chaikuad、Julien Diharce、Martin Schröder、Alicia Foucourt、Bertrand Leblond、Anne-Sophie Casagrande、Laurent Désiré、Pascal Bonnet、Stefan Knapp、Thierry Besson

  DOI：10.1021/acs.jmedchem.6b01083

  日期：2016.11.23

  Methyl 9-anilinothiazolo[5,4-f]quinazoline-2-carbimidates 1 (EHT 5372) and 2 (EHT 1610) are strong inhibitors of DYRK's family kinases. The crystal structures of the complex revealed a noncanonical binding mode of compounds I and 2 in DYRK2, explaining the remarkable selectivity and potency of these inhibitors. The structural data and comparison presented here provide therefore a template for further improvement of this inhibitor class and for the development of novel inhibitors selectively targeting DYRK kinases.