1-(hydroxybutylaminocarbonylmethyl)cytosine

• 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: 1-(hydroxybutylaminocarbonylmethyl)cytosine
• 英文别名: N-(4-Hydroxybutyl)-2-(4-imino-2-oxo-3,4-dihydro-1(2H)-pyrimidinyl)acetamide；2-(4-amino-2-oxopyrimidin-1-yl)-N-(4-hydroxybutyl)acetamide
• 化学式: C₁₀H₁₆N₄O₃
• 分子量: 240.262
• InChiKey: ORVPFQCLDDHQEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基-1-丁醇 、 1-ethoxycarbonylmethylcytosine 以 乙醇 为溶剂， 反应 5.0h， 以87%的产率得到1-(hydroxybutylaminocarbonylmethyl)cytosine
  参考文献：
  名称：

  Mikhailov, S.N.; Efimtseva, E.V.; Fomicheva, M.V., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 112 - 114

  摘要：

  DOI：

文献信息

• Acyclic Nucleoside and Nucleotide Analogues with Amide Bond
  作者：E. V. Efimtseva、S. N. Mikhailov、M. V. Jasko、D. V. Malakhov、D. G. Semizarcv、M. V. Fomicheva、E. R. Kern

  DOI：10.1080/15257779508012386

  日期：1995.5.1

  A series of acyclic nucleosides and related alpha-phosphonyl acyclic analogues of dNTP with an amide bond have been prepared. Their antiviral and substrate properties were investigated.New acyclic nucleoside analogues with a rigid structural element, amide bond, have been synthesized in two stages. Alkylation of bis- trimethylsilylated thymine, cytosine and sodium salt of adenine by ethyl bromoacetate gave ethoxycarbonylmethyl derivatives ($) under bar 1a-c. Reaction of ($) under bar 1a-c with aminoalcohols afforded acyclic nucleosides ($) under bar 2-($) under bar 4 in good yields (Scheme 1), These analogues were found to be inactive against HIV-1 (CEM-SS cells) and HSV -1, HSV-2, HCMV, VZV (HFF cells) at concentrations up to 100 mu g/ml and were nontoxic towards CEM and HFF cells. However, it was shown that triphosphate of ($) under bar 2c is incorporated into the DNA chain by DNA polymerase from HSV-1(1). The absence of antiviral activity and cytotoxicity is probably due to the fact that ($) under bar 2-($) under bar 4 are not recognized by cellular and viral kinases.
• Mikhailov, S.N.; Efimtseva, E.V.; Fomicheva, M.V., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 112 - 114
  作者：Mikhailov, S.N.、Efimtseva, E.V.、Fomicheva, M.V.、Rodionov, M.S.、Kern, E.R.

  DOI：——

  日期：——