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phenyl(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)methanone | 1160957-41-4

中文名称
——
中文别名
——
英文名称
phenyl(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)methanone
英文别名
phenyl-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl]methanone
phenyl(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)methanone化学式
CAS
1160957-41-4
化学式
C14H16N2O5
mdl
——
分子量
292.291
InChiKey
DAYXWTSHQYNLLQ-RAIGVLPGSA-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
  • 重原子数:
    21
  • 可旋转键数:
    6
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.29
  • 拓扑面积:
    127
  • 氢给体数:
    5
  • 氢受体数:
    6

反应信息

  • 作为产物:
    描述:
    2,2-二氟-2-苯乙腈1-氨基-1-脱氧-D-果糖乙酸盐sodium methylate 作用下, 以 甲醇 为溶剂, 反应 7.0h, 以34%的产率得到phenyl(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)methanone
    参考文献:
    名称:
    Inhibition of Sphingosine-1-Phosphate Lyase for the Treatment of Autoimmune Disorders
    摘要:
    During nearly a decade of research dedicated to the study of sphingosine signaling pathways, we identified sphingosine-1-phosphate lyase (S1PL) as a drug target for the treatment of autoimmune disorders. S1PL catalyzes the irreversible decomposition of sphingosine-1-phosphate (S1P) by a retro-aldol fragmentation that yields hexadecanaldehyde and phosphoethanolamine. Genetic models demonstrated that mice expressing reduced S1PL activity had decreased numbers of circulating lymphocytes due to altered lymphocyte trafficking, which prevented disease development in multiple models of autoimmune disease. Mechanistic studies of lymphoid tissue following oral administration of 2-acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxybutyl)-imidazole (THI) 3 showed a clear relationship between reduced lyase activity, elevated S I P levels, and lower levels of circulating lymphocytes. Our internal medicinal chemistry efforts discovered potent analogues of 3 bearing heterocycles as chemical equivalents of the pendant carbonyl present in the parent structure. Reduction of S1PL activity by oral administration of these analogues recapitulated the phenotype of mice with genetically reduced S1PL expression.
    DOI:
    10.1021/jm900278w
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