1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-5-fluorouracil | 121749-95-9

• 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-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-5-fluorouracil
• 英文别名: 1-[2-[Tert-butyl(dimethyl)silyl]oxyethoxymethyl]-5-fluoro-pyrimidine-2,4-dione；1-[2-[tert-butyl(dimethyl)silyl]oxyethoxymethyl]-5-fluoropyrimidine-2,4-dione
• CAS: 121749-95-9
• 化学式: C₁₃H₂₃FN₂O₄Si
• 分子量: 318.421
• InChiKey: MHLBLQMZBGWJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-5-fluorouracil 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-<(2-hydroxyethoxy)methyl>-6-(phenylselenenyl)-5-fluorouracil
  参考文献：
  名称：

  Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes

  摘要：

  Several 6-phenylselenenyl-substituted acyclouridine derivatives were prepared for evaluation as antiviral agents. Lithiation of the tert-butyldimethylsilyl-protected acyclonucleosides 4a-f with lithium diisopropylamide at -78-degrees-C, followed by reaction with diphenyl diselenide as an electrophile, and subsequent removal of the protecting group with tetra n-butylammonium fluoride gave 1-[(2-hydroxyethoxy)methyl]-6-(phenylselenenyl)uracils 6a-f in 50-70% overall yield. The potency and spectrum of activity of compounds 6a-f against HIV-1 in vitro was similar to HEPT (1), a related 6-phenylthio acyclonucleoside. However, whereas HEPT inhibited HIV-1 reverse transcriptase, the selenium-containing derivatives were ineffective, suggesting a different mechanism of action. Of significance was the finding that the 6-phenylselenenyl acyclonucleosides inhibited also HIV-2 in primary human lymphocytes.

  DOI：

  10.1021/jm00115a022
• 作为产物：
  描述：

  5-氟-1-(2-羟基乙氧基甲基)嘧啶-2,4-二酮 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-5-fluorouracil
  参考文献：
  名称：

  Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes

  摘要：

  Several 6-phenylselenenyl-substituted acyclouridine derivatives were prepared for evaluation as antiviral agents. Lithiation of the tert-butyldimethylsilyl-protected acyclonucleosides 4a-f with lithium diisopropylamide at -78-degrees-C, followed by reaction with diphenyl diselenide as an electrophile, and subsequent removal of the protecting group with tetra n-butylammonium fluoride gave 1-[(2-hydroxyethoxy)methyl]-6-(phenylselenenyl)uracils 6a-f in 50-70% overall yield. The potency and spectrum of activity of compounds 6a-f against HIV-1 in vitro was similar to HEPT (1), a related 6-phenylthio acyclonucleoside. However, whereas HEPT inhibited HIV-1 reverse transcriptase, the selenium-containing derivatives were ineffective, suggesting a different mechanism of action. Of significance was the finding that the 6-phenylselenenyl acyclonucleosides inhibited also HIV-2 in primary human lymphocytes.

  DOI：

  10.1021/jm00115a022

文献信息

• A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine
  作者：Tadashi Miyasaka、Hiromichi Tanaka、Masanori Baba、Hiroyuki Hayakawa、Richard T. Walker、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00132a002

  日期：1989.12
• BUNDGAARD, HANS;FALCH, ERIK;JENSEN, EJVIND, J. MED. CHEM., 32,(1989) N2, C. 2507-2509
  作者：BUNDGAARD, HANS、FALCH, ERIK、JENSEN, EJVIND

  DOI：——

  日期：——
• Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes
  作者：Naganna M. Goudgaon、Raymond F. Schinazi

  DOI：10.1021/jm00115a022

  日期：1991.11

  Several 6-phenylselenenyl-substituted acyclouridine derivatives were prepared for evaluation as antiviral agents. Lithiation of the tert-butyldimethylsilyl-protected acyclonucleosides 4a-f with lithium diisopropylamide at -78-degrees-C, followed by reaction with diphenyl diselenide as an electrophile, and subsequent removal of the protecting group with tetra n-butylammonium fluoride gave 1-[(2-hydroxyethoxy)methyl]-6-(phenylselenenyl)uracils 6a-f in 50-70% overall yield. The potency and spectrum of activity of compounds 6a-f against HIV-1 in vitro was similar to HEPT (1), a related 6-phenylthio acyclonucleoside. However, whereas HEPT inhibited HIV-1 reverse transcriptase, the selenium-containing derivatives were ineffective, suggesting a different mechanism of action. Of significance was the finding that the 6-phenylselenenyl acyclonucleosides inhibited also HIV-2 in primary human lymphocytes.