N¹-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine | 158666-07-0

• 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: N¹-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine
• 英文别名: 5-fluoro-1-(4'-hydroxy-2'-butynyl)cytosine；4-Amino-5-fluoro-1-(4-hydroxybut-2-ynyl)pyrimidin-2-one
• CAS: 158666-07-0
• 化学式: C₈H₈FN₃O₂
• 分子量: 197.169
• InChiKey: IMRUICCJMPVWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine 在 potassium tert-butylate 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (+/-)-N¹-(4-hydroxy-1,2-butadien-1-yl)-5-fluorocytosine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 5-Fluorocytallene: N-Dimethylaminomethylene as a Facilitating Group in Acetylene → Allene Isomerization

  摘要：

  The synthesis and biological activity of 5-fluorocytallene (3a) is described. 5-Fluorocytosine (4) was alkylated with 1-benzoyloxy-4-bromo-2-butyne (5) to give N-1-(4-benzoyloxy-2-butyn-1-yl)-5-fluorocytosine (6). Debenzoylation led to N-1-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine (7a). The latter compound was transformed to the N-4-dimethylaminomethylene derivative 8 which was isomerized in situ to the corresponding allene 9. Deprotection afforded 5-fluorocytallene (3a). Compound 3a suppressed the infectivity and replication of both laboratory and primary HIV-1 strains in vitro at nontoxic concentrations.

  DOI：

  10.1080/15257779408009480
• 作为产物：
  描述：

  N1-(4-benzoyl-2-butyn-1-yl)-5-fluorocytosine 在 氨 作用下， 以 甲醇 为溶剂， 以71%的产率得到N¹-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 5-Fluorocytallene: N-Dimethylaminomethylene as a Facilitating Group in Acetylene → Allene Isomerization

  摘要：

  The synthesis and biological activity of 5-fluorocytallene (3a) is described. 5-Fluorocytosine (4) was alkylated with 1-benzoyloxy-4-bromo-2-butyne (5) to give N-1-(4-benzoyloxy-2-butyn-1-yl)-5-fluorocytosine (6). Debenzoylation led to N-1-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine (7a). The latter compound was transformed to the N-4-dimethylaminomethylene derivative 8 which was isomerized in situ to the corresponding allene 9. Deprotection afforded 5-fluorocytallene (3a). Compound 3a suppressed the infectivity and replication of both laboratory and primary HIV-1 strains in vitro at nontoxic concentrations.

  DOI：

  10.1080/15257779408009480

文献信息

• Synthesis and Anti-HIV Activity of 5-Fluorocytallene: N-Dimethylaminomethylene as a Facilitating Group in Acetylene → Allene Isomerization
  作者：C. Simons、S. Chokekijchai、H. Mitsuya、J. Zemlicka

  DOI：10.1080/15257779408009480

  日期：1994.9

  The synthesis and biological activity of 5-fluorocytallene (3a) is described. 5-Fluorocytosine (4) was alkylated with 1-benzoyloxy-4-bromo-2-butyne (5) to give N-1-(4-benzoyloxy-2-butyn-1-yl)-5-fluorocytosine (6). Debenzoylation led to N-1-(4-hydroxy-2-butyn-1-yl)-5-fluorocytosine (7a). The latter compound was transformed to the N-4-dimethylaminomethylene derivative 8 which was isomerized in situ to the corresponding allene 9. Deprotection afforded 5-fluorocytallene (3a). Compound 3a suppressed the infectivity and replication of both laboratory and primary HIV-1 strains in vitro at nontoxic concentrations.