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8-cyclopentylmethoxycaffeine | 1314229-84-9

中文名称
——
中文别名
——
英文名称
8-cyclopentylmethoxycaffeine
英文别名
8-(cyclopentylmethoxy)-1,3,7-trimethylpurine-2,6-dione
8-cyclopentylmethoxycaffeine化学式
CAS
1314229-84-9
化学式
C14H20N4O3
mdl
——
分子量
292.338
InChiKey
BBMNPXACGURNQA-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):
    1.7
  • 重原子数:
    21
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.64
  • 拓扑面积:
    67.7
  • 氢给体数:
    0
  • 氢受体数:
    4

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

  • 作为产物:
    描述:
    咖啡因sodium 作用下, 以 氯仿 为溶剂, 反应 6.0h, 生成 8-cyclopentylmethoxycaffeine
    参考文献:
    名称:
    8-Aryl- and alkyloxycaffeine analogues as inhibitors of monoamine oxidase
    摘要:
    Recently it was reported that a series of 8-benzyloxycaffeine analogues are potent reversible inhibitors of human monoamine oxidase (MAO) A and B. In an attempt to discover additional C8 oxy substituents of caffeine that lead to potent MAO inhibition, a series of related 8-aryl- and alkyloxycaffeine analogues were synthesized and their MAO-A and -B inhibition potencies were compared to those of the 8-ben-zyloxycaffeines. The results document that while the 8-substituted-oxycaffeine analogues inhibited both human MAO isoforms, they displayed a high degree of selectivity for MAO-B. 8-(3-Phenylpropoxy) caffeine, 8-(2-phenoxyethoxy)caffeine and 8-[(5-methylhexyl)oxy]caffeine were found to be the especially potent MAO-B inhibitors with IC(50) values ranging from 0.38 to 0.62 mu M. These inhibitors are therefore 2.5-4.6 fold more potent MAO-B inhibitors than is 8-benzyloxycaffeine (IC(50) = 1.77 mu M). It is also demonstrated that, analogous to 8-benzyloxycaffeine, halogen substitution on the phenyl ring of the C8 substituent significantly enhances MAO binding affinity. For example, the most potent MAO-B inhibitor of the present series is 8-[2-(4-bromophenoxy)ethoxy]caffeine with an IC(50) value of 0.166 mu M. This study also reports possible binding orientations of selected oxy caffeines within the active site cavities of MAO-A and MAO-B. (C) 2011 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2011.05.014
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文献信息

  • 8-Aryl- and alkyloxycaffeine analogues as inhibitors of monoamine oxidase
    作者:Belinda Strydom、Jacobus J. Bergh、Jacobus P. Petzer
    DOI:10.1016/j.ejmech.2011.05.014
    日期:2011.8
    Recently it was reported that a series of 8-benzyloxycaffeine analogues are potent reversible inhibitors of human monoamine oxidase (MAO) A and B. In an attempt to discover additional C8 oxy substituents of caffeine that lead to potent MAO inhibition, a series of related 8-aryl- and alkyloxycaffeine analogues were synthesized and their MAO-A and -B inhibition potencies were compared to those of the 8-ben-zyloxycaffeines. The results document that while the 8-substituted-oxycaffeine analogues inhibited both human MAO isoforms, they displayed a high degree of selectivity for MAO-B. 8-(3-Phenylpropoxy) caffeine, 8-(2-phenoxyethoxy)caffeine and 8-[(5-methylhexyl)oxy]caffeine were found to be the especially potent MAO-B inhibitors with IC(50) values ranging from 0.38 to 0.62 mu M. These inhibitors are therefore 2.5-4.6 fold more potent MAO-B inhibitors than is 8-benzyloxycaffeine (IC(50) = 1.77 mu M). It is also demonstrated that, analogous to 8-benzyloxycaffeine, halogen substitution on the phenyl ring of the C8 substituent significantly enhances MAO binding affinity. For example, the most potent MAO-B inhibitor of the present series is 8-[2-(4-bromophenoxy)ethoxy]caffeine with an IC(50) value of 0.166 mu M. This study also reports possible binding orientations of selected oxy caffeines within the active site cavities of MAO-A and MAO-B. (C) 2011 Elsevier Masson SAS. All rights reserved.
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