4-N-benzylpyrimidine-4,6-diamine | 68027-76-9

• 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: 4-N-benzylpyrimidine-4,6-diamine
• 英文别名: N4-benzylpyrimidine-4,6-diamine；N⁴-benzyl-pyrimidine-4,6-diyldiamine；N⁴-Benzyl-pyrimidin-4,6-diyldiamin；4-Amino-6-benzylaminopyrimidine
• CAS: 68027-76-9
• 化学式: C₁₁H₁₂N₄
• 分子量: 200.243
• InChiKey: OSEJHFUKQYMCGF-UHFFFAOYSA-N

物化性质

• 沸点：
  423.0±35.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-N-benzylpyrimidine-4,6-diamine 、 异硫氰酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以51%的产率得到1-(6-(benzylamino)pyrimidin-4-yl)-3-ethylthiourea
  参考文献：
  名称：

  Development of Multifunctional Pyrimidinylthiourea Derivatives as Potential Anti-Alzheimer Agents

  摘要：

  Starting from a screening-hit compound, via structure modifications and optimizations, a series of nonfused and nonassembly pyrimidinylthiourea derivatives (2-5) was designed, synthesized, and evaluated as novel multifunctional agents against Alzheimer's disease. Biological activity results demonstrated that compounds 5r and 5t exhibited potent inhibition and excellent selectivity toward acetylcholinesterase (AChE, Sr, IC50 = 0.204 mu M, SI > 196; St, IC50 = 0.067 mu M, SI > 597), specific metal-chelating ability, significant antioxidant effects, modulation of metal-induced A beta aggregation, inhibition of ROS production by copper redox cycle, low cytotoxicity, and moderate neuroprotection to human neuroblastoma SH-SY5Y cells. Moreover, compound Sr displayed appropriate blood brain barrier (BBB) permeability both in vitro and in vivo and could improve memory and cognitive function of, scopolamine-induced amnesia mice. The multifunctional profiles of Sr and its effectivity in AD mice highlight these structurally distinct pyrimidinylthiourea derivatives as prospective prototypes in the research of innovative multifunctional drugs for Alzheimer's disease.

  DOI：

  10.1021/acs.jmedchem.6b00636
• 作为产物：
  描述：

  4-氨基-6-氯嘧啶 、 苄胺 在 caesium carbonate 作用下， 反应 12.0h， 以66%的产率得到4-N-benzylpyrimidine-4,6-diamine
  参考文献：
  名称：

  取代嘧啶脲类化合物及其用途

  摘要：

  本发明涉及一种取代嘧啶脲类化合物及其用途。所述取代嘧啶脲类化合物为式I所示化合物(具体结构请见说明书或权利要求书)、或其立体异构体或药学上可接受的盐。体外活性测试表明：本发明公开的取代嘧啶脲类化合物具有胆碱酯酶抑制活性、螯合金属离子、抑制金属离子诱导的自由基产生和抑制金属离子诱导的Aβ聚集等性能。因此，本发明提供的取代嘧啶脲类化合物有望被用于制备治疗和/或预防阿尔茨海默病药物。

  公开号：

  CN105418592B

文献信息

• Solid Phase Synthesis of Diamino-Substituted Pyrimidines
  作者：Caterina Barillari、Daniela Barlocco、Luca F. Raveglia

  DOI：10.1002/1099-0690(200112)2001:24<4737::aid-ejoc4737>3.0.co;2-1

  日期：2001.12

  2,4- and 4,6-Diamino-substituted pyrimidines are known for their biological activity in many therapeutic areas. A novel solid-phase synthesis of this class of compounds by nucleophilic aromatic substitution has been set up and the reactivity of differently substituted solid-supported pyrimidines with properly selected amines has been studied, Using this methodology a small library of diamino-substituted pyrimidines has been prepared.
• MEDIA, KITS, SYSTEMS AND METHODS FOR THE MICROPROPAGATION OF MONOCOTYLEDONOUS PLANTS
  申请人：Burr Randall W.

  公开号：US20120159847A1

  公开（公告）日：2012-06-28

  Disclosed herein are media, systems and methods for achieving micropropagation of monocotyledonous plants.
• Media, Kits, Systems and Methods for the Micropropagation of Bamboo
  申请人：Burr Randall W.

  公开号：US20120220036A1

  公开（公告）日：2012-08-30

  Disclosed herein are media, kits, systems and methods for achieving micropropagation of bamboo on a commercially-relevant scale.
• MEDIA, KITS, SYSTEMS AND METHODS FOR THE MICROPROPAGATION OF BAMBOO
  申请人：Burr Randall W.

  公开号：US20120264216A1

  公开（公告）日：2012-10-18

  Disclosed herein are media, kits, systems and methods for achieving micropropagation of bamboo on a commercially-relevant scale.
• US8435789B2
  申请人：——

  公开号：US8435789B2

  公开（公告）日：2013-05-07