N-(benzothiazol-6-yl)-6-chloro-N'-(benzyl-methyl-amino)-[1,3,5]-triazin-2,4-diamine | 797039-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: N-(benzothiazol-6-yl)-6-chloro-N'-(benzyl-methyl-amino)-[1,3,5]-triazin-2,4-diamine
• 英文别名: 4-N-(1,3-benzothiazol-6-yl)-2-N-benzyl-6-chloro-2-N-methyl-1,3,5-triazine-2,4-diamine
• CAS: 797039-39-5
• 化学式: C₁₈H₁₅ClN₆S
• 分子量: 382.876
• InChiKey: WPJDXFPVEGTFDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(benzothiazol-6-yl)-6-chloro-N'-(benzyl-methyl-amino)-[1,3,5]-triazin-2,4-diamine 在 三氟乙酸 作用下， 反应 4.0h， 以72%的产率得到4-(Benzothiazol-6-ylamine)-6-(methyl-benzylamino)-[1,3,5]triazin-2-ol
  参考文献：
  名称：

  2-Hydroxy-4,6-diamino-[1,3,5]triazines: A Novel Class of VEGF-R2 (KDR) Tyrosine Kinase Inhibitors

  摘要：

  2-Hydroxy-4,6-diamino-[1,3,5]triazines are described which are a novel class of potent inhibitors of the VEGF-R2 (flk-1/KDR) tyrosine kinase. 4-(Benzothiazol-6-ylamino)-6-(benzyl-isopropyl-amino)-[1,3,5]triazin-2-ol (14d) exhibited low nanomolar potency in the in vitro enzyme inhibition assay (IC50 = 18 nM) and submicromolar inhibitory activity in a KDR-induced MAP kinase autophosphorylation assay in HUVEC cells (IC50 = 280 nM), and also demonstrated good in vitro selectivity against a panel of growth factor receptor tyrosine kinases. Further, 14d showed antiangiogenic activity in an aortic ring explant assay by blocking endothelial outgrowths in rat aortas with an IC50 of 1 mu M.

  DOI：

  10.1021/jm049372z
• 作为产物：
  描述：

  6-氨基苯并噻唑 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 N-(benzothiazol-6-yl)-6-chloro-N'-(benzyl-methyl-amino)-[1,3,5]-triazin-2,4-diamine
  参考文献：
  名称：

  2-Hydroxy-4,6-diamino-[1,3,5]triazines: A Novel Class of VEGF-R2 (KDR) Tyrosine Kinase Inhibitors

  摘要：

  2-Hydroxy-4,6-diamino-[1,3,5]triazines are described which are a novel class of potent inhibitors of the VEGF-R2 (flk-1/KDR) tyrosine kinase. 4-(Benzothiazol-6-ylamino)-6-(benzyl-isopropyl-amino)-[1,3,5]triazin-2-ol (14d) exhibited low nanomolar potency in the in vitro enzyme inhibition assay (IC50 = 18 nM) and submicromolar inhibitory activity in a KDR-induced MAP kinase autophosphorylation assay in HUVEC cells (IC50 = 280 nM), and also demonstrated good in vitro selectivity against a panel of growth factor receptor tyrosine kinases. Further, 14d showed antiangiogenic activity in an aortic ring explant assay by blocking endothelial outgrowths in rat aortas with an IC50 of 1 mu M.

  DOI：

  10.1021/jm049372z

文献信息

• 2-Hydroxy-4,6-diamino-[1,3,5]triazines: A Novel Class of VEGF-R2 (KDR) Tyrosine Kinase Inhibitors
  作者：Nand Baindur、Naresh Chadha、Benjamin M. Brandt、Davoud Asgari、Raymond J. Patch、Celine Schalk-HiHi、Theodore E. Carver、Ioanna P. Petrounia、Christian A. Baumann、Heidi Ott、Carl Manthey、Barry A. Springer、Mark R. Player

  DOI：10.1021/jm049372z

  日期：2005.3.1

  2-Hydroxy-4,6-diamino-[1,3,5]triazines are described which are a novel class of potent inhibitors of the VEGF-R2 (flk-1/KDR) tyrosine kinase. 4-(Benzothiazol-6-ylamino)-6-(benzyl-isopropyl-amino)-[1,3,5]triazin-2-ol (14d) exhibited low nanomolar potency in the in vitro enzyme inhibition assay (IC50 = 18 nM) and submicromolar inhibitory activity in a KDR-induced MAP kinase autophosphorylation assay in HUVEC cells (IC50 = 280 nM), and also demonstrated good in vitro selectivity against a panel of growth factor receptor tyrosine kinases. Further, 14d showed antiangiogenic activity in an aortic ring explant assay by blocking endothelial outgrowths in rat aortas with an IC50 of 1 mu M.