6-amino-4-(2-chlorophenyl)-3,4-dihydro-1,3,5-triazin-2(1H)-one | 38261-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 6-amino-4-(2-chlorophenyl)-3,4-dihydro-1,3,5-triazin-2(1H)-one
• 英文别名: o-Chlor-1,5-benzylidenguanylharnstoff；6-amino-4-(2-chloro-phenyl)-3,4-dihydro-1H-[1,3,5]triazin-2-one
• CAS: 38261-38-0
• 化学式: C₉H₉ClN₄O
• 分子量: 224.65
• InChiKey: HPHYTMHSQGMYIR-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 、 脒基脲硫酸盐 在 硫酸 作用下， 反应 72.0h， 以64%的产率得到6-amino-4-(2-chlorophenyl)-3,4-dihydro-1,3,5-triazin-2(1H)-one
  参考文献：
  名称：

  3,4-Dihydro-1,3,5-triazin-2(1H)-ones as the First Dual BACE-1/GSK-3β Fragment Hits against Alzheimer’s Disease

  摘要：

  One of the main obstacles toward the discovery of effective anti-Alzheimer drugs is the multifactorial nature of its etiopathology. Therefore, the use of multitarget-directed ligands has emerged as particularly suitable. Such ligands, able to modulate different neurodegenerative pathways, for example, amyloid and tau cascades, as well as cognitive and neurogenic functions, are fostered to come. In this respect, we report herein on the first class of BACE-1/GSK-3 beta dual inhibitors based on a 3,4-dihydro-1,3,5-triazin-2(1H)-one skeleton, whose hit compound 1 showed interesting properties in a preliminary investigation. Notably, compound 2, endowed with well-balanced potencies against the two isolated enzymes (IC50 of 16 and 7 mu M against BACE-1 and GSK-3 beta, respectively), displayed effective neuroprotective and neurogenic activities and no neurotoxicity in cell-based assays. It also showed good brain permeability in a pharmacokinetic assessment in mice. Overall, triazinone derivatives, thanks to the simultaneous modulation of multiple points of the diseased network, might emerge as suitable candidates to be tested in in vivo Alzheimer's disease models.

  DOI：

  10.1021/acschemneuro.5b00121