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5-(4-Benzyloxy-benzyloxy)-pyrimidine-2,4-diamine

中文名称
——
中文别名
——
英文名称
5-(4-Benzyloxy-benzyloxy)-pyrimidine-2,4-diamine
英文别名
5-[(4-phenylmethoxyphenyl)methoxy]pyrimidine-2,4-diamine
5-(4-Benzyloxy-benzyloxy)-pyrimidine-2,4-diamine化学式
CAS
——
化学式
C18H18N4O2
mdl
——
分子量
322.367
InChiKey
ZASVHVWYIHBJJR-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):
    2.4
  • 重原子数:
    24
  • 可旋转键数:
    6
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.11
  • 拓扑面积:
    96.3
  • 氢给体数:
    2
  • 氢受体数:
    6

反应信息

  • 作为产物:
    描述:
    4-苄氧基氯化苄 、 2,4-diamino-5-hydroxypyrimidine dihydrochloride 在 甲氧基乙醇钠 、 potassium iodide 作用下, 以 乙二醇甲醚 为溶剂, 反应 72.5h, 以54%的产率得到5-(4-Benzyloxy-benzyloxy)-pyrimidine-2,4-diamine
    参考文献:
    名称:
    Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against Candida albicansSynthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4‘-Substituted 4-Aminodiphenyl Sulfones
    摘要:
    The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were synthesized and tested as inhibitors of DHFR and compared with their activity against DHFR derived from mycobacteria and Escherichia coli. To test for selectivity, also rat DHFR was used. A series of substituted 4-aminodiphenyl sulfones was tested for inhibitory activity against SYN and the I-50 values compared to those obtained previously against Plasmodium berghei- and E. coli-derived SYN. Surprisingly, QSAR equations show very similar structural dependencies. To find an explanation for the large difference in the I-50 values observed for enzyme inhibition (SYN, DHFR) and for inhibition of cell cultures of Candida, mutant strains with overexpressed efflux pumps and strains in which such pumps are deleted were included in the study and the MICs compared. Efflux pumps were responsible for the low activity of some of the tested derivatives, others showed no increase in activity after pumps were knocked out. In this case it may be speculated that these derivatives are not able to enter the cells.
    DOI:
    10.1021/jm030931w
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