(2R,4S,5S)-1--2-furanyl>thymine | 132178-47-3

• 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: (2R,4S,5S)-1--2-furanyl>thymine
• 英文别名: (2R,4S,5S)-1-{tetrahydro-4-(phenylselenyl)-5-[(dimethoxyphosphinyl)methoxy]-2-furanyl}thymine
• CAS: 132178-47-3
• 化学式: C₁₈H₂₃N₂O₇PSe
• 分子量: 489.324
• InChiKey: YZQSPOXHMXYZJZ-UXLLHSPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-1--2-furanyl>thymine 在 sodium periodate 、 三甲基溴硅烷 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 5.75h， 生成 (2R,5R)-1-<2,5-dihydro-5-(phosphonomethoxy)-2-furanyl>thymine disodium salt
  参考文献：
  名称：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV

  摘要：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates. Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared. Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate. Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage. The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).

  DOI：

  10.1021/jo00008a013
• 作为产物：
  描述：

  (2'R)-1-(2,3-dihydrofuran-2-yl)thymine 在 silver perchlorate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.05h， 生成 (2R,4S,5S)-1--2-furanyl>thymine
  参考文献：
  名称：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV

  摘要：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates. Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared. Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate. Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage. The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).

  DOI：

  10.1021/jo00008a013

文献信息

• Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates
  作者：Richard L. Mackman、Constantine G. Boojamra、Vidya Prasad、Lijun Zhang、Kuei-Ying Lin、Oleg Petrakovsky、Darius Babusis、James Chen、Janet Douglas、Deborah Grant、Hon C. Hui、Choung U. Kim、David Y. Markevitch、Jennifer Vela、Adrian Ray、Tomas Cihlar

  DOI：10.1016/j.bmcl.2007.10.038

  日期：2007.12

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.