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4,6-dichloro-5-[(3-bromophenyl)methylamino]pyrimidine | 454685-39-3

中文名称
——
中文别名
——
英文名称
4,6-dichloro-5-[(3-bromophenyl)methylamino]pyrimidine
英文别名
N-(3-bromophenyl)-4,6-dichloro-N-methylpyrimidin-5-amine
4,6-dichloro-5-[(3-bromophenyl)methylamino]pyrimidine化学式
CAS
454685-39-3
化学式
C11H8BrCl2N3
mdl
——
分子量
333.015
InChiKey
STNHMRFWKBPETK-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.5
  • 重原子数:
    17
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.09
  • 拓扑面积:
    29
  • 氢给体数:
    0
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    4,6-dichloro-5-[(3-bromophenyl)methylamino]pyrimidine氢碘酸 、 sodium iodide 作用下, 以 乙醇丙酮 为溶剂, 生成 N5-(3-Bromo-phenyl)-6-iodo-N5-methyl-pyrimidine-4,5-diamine
    参考文献:
    名称:
    Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors
    摘要:
    Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.
    DOI:
    10.1021/jm020049a
  • 作为产物:
    描述:
    参考文献:
    名称:
    Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors
    摘要:
    Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.
    DOI:
    10.1021/jm020049a
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文献信息

  • Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors
    作者:Arthur Gomtsyan、Stanley Didomenico、Chih-Hung Lee、Mark A. Matulenko、Ki Kim、Elizabeth A. Kowaluk、Carol T. Wismer、Joe Mikusa、Haixia Yu、Kathy Kohlhaas、Michael F. Jarvis、Shripad S. Bhagwat
    DOI:10.1021/jm020049a
    日期:2002.8.1
    Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.
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同类化合物

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