5'-Desoxythymidin-5'-carbonitril | 22567-00-6

• 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: 5'-Desoxythymidin-5'-carbonitril
• 英文别名: 5'-Cyano-5'-deoxythymidin；2-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetonitrile
• CAS: 22567-00-6
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: GFEHCLIOGBFOAP-DJLDLDEBSA-N

物化性质

• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-Desoxythymidin-5'-carbonitril 在 barium sulfate 、 1,3-丙二醇 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1-[2,5,6-trideoxy-6-(3-methyl-1-nitrosoureido)-β-D-erythro-hexofuranosyl]thymine
  参考文献：
  名称：

  Nucleosides containing chemically reactive groups

  摘要：

  5'-Amino-5'-deoxyinosine (1) and 1-(6-amino-2,5,6-trideoxy-beta-D-erythro-hexofuranosyl)thymine (9) were prepared and substituted on the amino group with chemically reactive functions in an effort to find inhibitors of enzymes that metabolize the corresponding nucleotides. The resulting 5'-substituted methynitrosoureas 3, 11a, and 11b, bromoacetamides 4 and 13, phenyl carbamates 5 and 14, and 4-(fluorosulfonyl)benzamides 6 and 15 were tested for cytotoxicity to H.Ep-2 cells in culture and as inhibitors of incorporation of precursors into nucleic acids of L1210 cells. The inosine derivatives were also evaluated as inhibitors of hypoxanthine phosphoribosyltransferase. Compounds 4, 6 and 13 showed moderate inhibition of formation of nucleic acids, and compound 4 demonstrated significant cytotoxicity (ED50 less than 5 microgram/mL).

  DOI：

  10.1021/jm00135a021
• 作为产物：
  描述：

  3'-O-Acetyl-5'-desoxythymidin-5'-carbonitril 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以76%的产率得到5'-Desoxythymidin-5'-carbonitril
  参考文献：
  名称：

  Meyer, Wilfried; Frollmann, Hartmut, Chemische Berichte, 1980, vol. 113, # 7, p. 2530 - 2544

  摘要：

  DOI：

文献信息

• HIEBL, JOHANN;ZBIRAL, ERICH;BALZARINI, JAN;DE, CLERCQ ERIK, J. MED. CHEM., 34,(1991) N, C. 1426-1430
  作者：HIEBL, JOHANN、ZBIRAL, ERICH、BALZARINI, JAN、DE, CLERCQ ERIK

  DOI：——

  日期：——
• Meyer, Wilfried; Frollmann, Hartmut, Chemische Berichte, 1980, vol. 113, # 7, p. 2530 - 2544
  作者：Meyer, Wilfried、Frollmann, Hartmut

  DOI：——

  日期：——
• Nucleosides containing chemically reactive groups
  作者：Robert D. Elliott、R. Wallace Brockman、John A. Montgomery

  DOI：10.1021/jm00135a021

  日期：1981.3

  5'-Amino-5'-deoxyinosine (1) and 1-(6-amino-2,5,6-trideoxy-beta-D-erythro-hexofuranosyl)thymine (9) were prepared and substituted on the amino group with chemically reactive functions in an effort to find inhibitors of enzymes that metabolize the corresponding nucleotides. The resulting 5'-substituted methynitrosoureas 3, 11a, and 11b, bromoacetamides 4 and 13, phenyl carbamates 5 and 14, and 4-(fluorosulfonyl)benzamides 6 and 15 were tested for cytotoxicity to H.Ep-2 cells in culture and as inhibitors of incorporation of precursors into nucleic acids of L1210 cells. The inosine derivatives were also evaluated as inhibitors of hypoxanthine phosphoribosyltransferase. Compounds 4, 6 and 13 showed moderate inhibition of formation of nucleic acids, and compound 4 demonstrated significant cytotoxicity (ED50 less than 5 microgram/mL).