N⁴-ethyloxycarbonyl-cytosine | 25726-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N⁴-ethyloxycarbonyl-cytosine
• 英文别名: N-Carbethoxycytosin；(2-oxo-1,2-dihydro-pyrimidin-4-yl)-carbamic acid ethyl ester；ethyl N-(2-oxo-1H-pyrimidin-6-yl)carbamate
• CAS: 25726-35-6
• 化学式: C₇H₉N₃O₃
• 分子量: 183.167
• InChiKey: MNEXOCHOUJNLMB-UHFFFAOYSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胞嘧啶 、 氯甲酸乙酯 在 吡啶 作用下， 以92%的产率得到N⁴-ethyloxycarbonyl-cytosine
  参考文献：
  名称：

  N4-alkyloxycarbonyl derivatives of cytosine: physicochemical characterisation, and cytosine regeneration rates and release from alginic acid gels

  摘要：

  Nucleobase containing compounds might constitute a potential alternative to conventional antibiotics in the treatment of Helicobacter pylori infections. N-4-alkyloxycarbonyl-cytosine derivatives were synthesized and subjected to basic physicochemical characterisation including assessment of hydrolytic stability in various matrices. pH-rate profiles of selected compounds (range 0-12) were constructed. Hydrolysis of the derivatives in slightly alkaline solution (60degreesC) resulted in quantitative conversion to parent cytosine whereas at acidic pH (60degreesC) liberation of cytosine was in most cases accompanied by the parallel formation of uracil. Interestingly the lipophilic N-4-adamantyloxycarbonyl-cytosine prodrug exhibited a half-life of 41 min (pH 1.1 at 37degreesC) with quantitative conversion to parent cytosine, the degradation rate being approximately 200 times faster than that of the non-cyclic aliphatic derivatives investigated. The presence of pig stomach homogenates, pepsin A and H. pylori did not have a noteworthy catalytic effect on the hydrolysis of the derivatives. The release of parent cytosine was markedly delayed from alginic acid gels loaded with the acid-labile and poorly soluble ADC prodrug as compared to gels loaded with parent cytosine. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2004.08.007

文献信息

• AUZOU, G.;RIPS, R., J. HETEROCYCL. CHEM., 1981, 18, N 4, 835-836
  作者：AUZOU, G.、RIPS, R.

  DOI：——

  日期：——
• N4-alkyloxycarbonyl derivatives of cytosine: physicochemical characterisation, and cytosine regeneration rates and release from alginic acid gels
  作者：Karsten Petersson、Brian Thoning Pedersen、Dan Stærk、Karen A. Krogfelt、Claus Larsen

  DOI：10.1016/j.ejps.2004.08.007

  日期：2004.12

  Nucleobase containing compounds might constitute a potential alternative to conventional antibiotics in the treatment of Helicobacter pylori infections. N-4-alkyloxycarbonyl-cytosine derivatives were synthesized and subjected to basic physicochemical characterisation including assessment of hydrolytic stability in various matrices. pH-rate profiles of selected compounds (range 0-12) were constructed. Hydrolysis of the derivatives in slightly alkaline solution (60degreesC) resulted in quantitative conversion to parent cytosine whereas at acidic pH (60degreesC) liberation of cytosine was in most cases accompanied by the parallel formation of uracil. Interestingly the lipophilic N-4-adamantyloxycarbonyl-cytosine prodrug exhibited a half-life of 41 min (pH 1.1 at 37degreesC) with quantitative conversion to parent cytosine, the degradation rate being approximately 200 times faster than that of the non-cyclic aliphatic derivatives investigated. The presence of pig stomach homogenates, pepsin A and H. pylori did not have a noteworthy catalytic effect on the hydrolysis of the derivatives. The release of parent cytosine was markedly delayed from alginic acid gels loaded with the acid-labile and poorly soluble ADC prodrug as compared to gels loaded with parent cytosine. (C) 2004 Elsevier B.V. All rights reserved.