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5',4N-bis<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>-2',3'-dideoxycytidine

中文名称
——
中文别名
——
英文名称
5',4N-bis<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>-2',3'-dideoxycytidine
英文别名
5',4N-bis[(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl]-2',3'-dideoxycytidine;[(2S,5R)-5-[4-[(1-methyl-4H-pyridine-3-carbonyl)amino]-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 1-methyl-4H-pyridine-3-carboxylate
5',4N-bis<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>-2',3'-dideoxycytidine化学式
CAS
——
化学式
C23H27N5O5
mdl
——
分子量
453.498
InChiKey
MICHLJWXTWDTGH-AZUAARDMSA-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):
    1.1
  • 重原子数:
    33
  • 可旋转键数:
    7
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.39
  • 拓扑面积:
    104
  • 氢给体数:
    1
  • 氢受体数:
    7

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:
    5',4N-bis<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>-2',3'-dideoxycytidine氢氧化钾 作用下, 以46%的产率得到5'-<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>-2',3'-dideoxycytidine
    参考文献:
    名称:
    Synthesis and pharmacokinetics of a dihydropyridine chemical delivery system for the antiimmunodeficiency virus agent, dideoxycytidine
    摘要:
    In order to explore the possibility that a dihydropyridine/pyridinium redox chemical delivery system might enhance significantly the brain uptake of the anti-HIV agent dideoxycytidine (DDC), we prepared a DDC derivative which bore the 1,4-dihydro-1-methyl-3-pyridylcarbonyl moiety at both the cytidine exocyclic amino moiety and the sugar 5'-hydroxyl function; namely, [(1,4N-bis-[(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl]-2',3'-dideoxycytidine(2). In cell-free extracts of rat brain tissue, compound 2 was readily converted to free DDC by stepwise oxidation and hydrolysis of the dihydropyridyl groups. Time-dependent plasma and brain concentrations of DDC and 2 were determined following iv administration of 2 (49.3 mg/kg) to rats. Compound 2 could be detected in brain, reaching peak concentrations of 7.7 +/- 2.9 nmol/g at 15 min. Low levels of DDC also were detected with a peak concentration of 1.4 +/- 0.5 nmol/g at 240 min after injection. The brain/plasma concentration integral of compound 2 was 0.95 whereas that for DDC in brain as a ratio of combined DDC and compound 2 levels in plasma was 0.24. Despite this, brain concentrations remained low and not significantly different from those achieved following administration of DDC alone.
    DOI:
    10.1021/jm00057a002
  • 作为产物:
    参考文献:
    名称:
    Synthesis and pharmacokinetics of a dihydropyridine chemical delivery system for the antiimmunodeficiency virus agent, dideoxycytidine
    摘要:
    In order to explore the possibility that a dihydropyridine/pyridinium redox chemical delivery system might enhance significantly the brain uptake of the anti-HIV agent dideoxycytidine (DDC), we prepared a DDC derivative which bore the 1,4-dihydro-1-methyl-3-pyridylcarbonyl moiety at both the cytidine exocyclic amino moiety and the sugar 5'-hydroxyl function; namely, [(1,4N-bis-[(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl]-2',3'-dideoxycytidine(2). In cell-free extracts of rat brain tissue, compound 2 was readily converted to free DDC by stepwise oxidation and hydrolysis of the dihydropyridyl groups. Time-dependent plasma and brain concentrations of DDC and 2 were determined following iv administration of 2 (49.3 mg/kg) to rats. Compound 2 could be detected in brain, reaching peak concentrations of 7.7 +/- 2.9 nmol/g at 15 min. Low levels of DDC also were detected with a peak concentration of 1.4 +/- 0.5 nmol/g at 240 min after injection. The brain/plasma concentration integral of compound 2 was 0.95 whereas that for DDC in brain as a ratio of combined DDC and compound 2 levels in plasma was 0.24. Despite this, brain concentrations remained low and not significantly different from those achieved following administration of DDC alone.
    DOI:
    10.1021/jm00057a002
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