6-amino-5-{[1-(3-chlorophenyl)-meth-(E)-ylidene]-amino}-1,3-dimethyl-1H-pyrimidine-2,4-dione | 1198748-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-amino-5-{[1-(3-chlorophenyl)-meth-(E)-ylidene]-amino}-1,3-dimethyl-1H-pyrimidine-2,4-dione
• CAS: 1198748-31-0
• 化学式: C₁₃H₁₃ClN₄O₂
• 分子量: 292.725
• InChiKey: OTHVGMWIYREQBE-FRKPEAEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-amino-5-{[1-(3-chlorophenyl)-meth-(E)-ylidene]-amino}-1,3-dimethyl-1H-pyrimidine-2,4-dione 、 原甲酸三乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以27.1%的产率得到6-(3-chlorophenyl)-1,3-dimethyl-1H-pteridine-2,4-dione
  参考文献：
  名称：

  Synthesis and in vitro evaluation of pteridine analogues as monoamine oxidase B and nitric oxide synthase inhibitors

  摘要：

  Monoamine oxidase B (MAO-B) and nitric oxide synthase (NOS) have both been implicated in the pathology of neurodegenerative diseases. In an attempt to design dual-target-directed drugs that inhibit both these enzymes, a series of pteridine-2,4-dione analogues were synthesised. The compounds were found to be relatively weak NOS inhibitors but showed promising MAO-B activity with 6-amino-5-[(E)-3-(3-chloro-phenyl)-prop-2-en-(E)-ylideneamino]-1,3-dimethyl-1H-pyrimidine-2,4-dione and 6-[(E)-2-(3-chloro-phenyl)-vinyl]-1,3-dimethyl-1H-pteridine-2,4-dione inhibiting MAO-B with IC50 values of 0.602 and 0.314 mu M, respectively. The pteridine-2,4-dione analogues thus show promise as scaffolds for the development of potent reversible MAO-B inhibitors and as observed in earlier studies, the most potent inhibitors were obtained with 3-chlorostyryl substitution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.019
• 作为产物：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 、 3-氯苯甲醛 以 乙醇 为溶剂， 反应 4.0h， 以78.6%的产率得到6-amino-5-{[1-(3-chlorophenyl)-meth-(E)-ylidene]-amino}-1,3-dimethyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and in vitro evaluation of pteridine analogues as monoamine oxidase B and nitric oxide synthase inhibitors

  摘要：

  Monoamine oxidase B (MAO-B) and nitric oxide synthase (NOS) have both been implicated in the pathology of neurodegenerative diseases. In an attempt to design dual-target-directed drugs that inhibit both these enzymes, a series of pteridine-2,4-dione analogues were synthesised. The compounds were found to be relatively weak NOS inhibitors but showed promising MAO-B activity with 6-amino-5-[(E)-3-(3-chloro-phenyl)-prop-2-en-(E)-ylideneamino]-1,3-dimethyl-1H-pyrimidine-2,4-dione and 6-[(E)-2-(3-chloro-phenyl)-vinyl]-1,3-dimethyl-1H-pteridine-2,4-dione inhibiting MAO-B with IC50 values of 0.602 and 0.314 mu M, respectively. The pteridine-2,4-dione analogues thus show promise as scaffolds for the development of potent reversible MAO-B inhibitors and as observed in earlier studies, the most potent inhibitors were obtained with 3-chlorostyryl substitution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.019

文献信息

• Synthesis and in vitro evaluation of pteridine analogues as monoamine oxidase B and nitric oxide synthase inhibitors
  作者：Louis H.A. Prins、Jacobus P. Petzer、Sarel F. Malan

  DOI：10.1016/j.bmc.2009.09.019

  日期：2009.11

  Monoamine oxidase B (MAO-B) and nitric oxide synthase (NOS) have both been implicated in the pathology of neurodegenerative diseases. In an attempt to design dual-target-directed drugs that inhibit both these enzymes, a series of pteridine-2,4-dione analogues were synthesised. The compounds were found to be relatively weak NOS inhibitors but showed promising MAO-B activity with 6-amino-5-[(E)-3-(3-chloro-phenyl)-prop-2-en-(E)-ylideneamino]-1,3-dimethyl-1H-pyrimidine-2,4-dione and 6-[(E)-2-(3-chloro-phenyl)-vinyl]-1,3-dimethyl-1H-pteridine-2,4-dione inhibiting MAO-B with IC50 values of 0.602 and 0.314 mu M, respectively. The pteridine-2,4-dione analogues thus show promise as scaffolds for the development of potent reversible MAO-B inhibitors and as observed in earlier studies, the most potent inhibitors were obtained with 3-chlorostyryl substitution. (C) 2009 Elsevier Ltd. All rights reserved.