(2'R)-1-(2,3-dihydrofuran-2-yl)thymine | 37076-62-3

• 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: (2'R)-1-(2,3-dihydrofuran-2-yl)thymine
• 英文别名: 1-[(2R)-2,3-dihydrofuran-2-yl]-5-methyl-3H-pyrimidine-2,4-dione；1-(D-2,3-Dihydrofuryl)thymin；1-(2,3-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione；1-[(2R)-2,3-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 37076-62-3
• 化学式: C₉H₁₀N₂O₃
• 分子量: 194.19
• InChiKey: ATSOCGZHGGWROO-SSDOTTSWSA-N

物化性质

• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2'R)-1-(2,3-dihydrofuran-2-yl)thymine 在 sodium periodate 、 silver perchlorate 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.8h， 生成 (2R,5R)-1-<2,5-dihydro-5-<(dimethoxyphosphinyl)methoxy>-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
• 作为产物：
  描述：

  胸腺嘧啶脱氧核苷-5-羧酸 在 neopentylacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到(2'R)-1-(2,3-dihydrofuran-2-yl)thymine
  参考文献：
  名称：

  Isosteric triphosphonate analogues of dNTP: Synthesis and substrate properties toward various DNA polymerases

  摘要：

  Isosteric triphosphonate derivatives of 2',3'-dideoxy-2',3'-didehydroadenosine and 3'-deoxy-2',3'-didehydrothymidine and their beta,gamma-substituted analogues were synthesized. Their substrate properties toward a number of reverse transcriptases of the human immunodeficiency and avian myeloblastosis viruses, human DNA polymerases alpha and beta, and the Klenow fragment of Escherichia coli DNA polymerase I were studied.

  DOI：

  10.1134/s1068162007050056

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.
• KIM, CHOUNG UN;LUH, BING Y.;MARTIN, JOHN C., J. ORG. CHEM., 56,(1991) N, C. 2642-2647
  作者：KIM, CHOUNG UN、LUH, BING Y.、MARTIN, JOHN C.

  DOI：——

  日期：——
• KIM, CHOUNG UN;LUH, BING Y.;MISCO, PETER F.;MARTIN, JOHN C., NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 371-375
  作者：KIM, CHOUNG UN、LUH, BING Y.、MISCO, PETER F.、MARTIN, JOHN C.

  DOI：——

  日期：——
• CYCLOPENTENE-OXYMETHYLENE PHOSPHONAMIDATES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2024107859A1

  公开（公告）日：2024-05-23

  Substituted cyclopentene-oxymethylene phosphonamidates and related compounds, pharmaceutical compositions, their use for inhibiting LINE1 reverse transcriptase and/or HERV- K reverse transcriptase activity, and their use in the treatment of medical disorders, such as cancer, are disclosed herein.
• Isosteric triphosphonate analogues of dNTP: Synthesis and substrate properties toward various DNA polymerases
  作者：A. Yu. Skoblov、A. N. Semenyuk、A. M. Murabuldaev、V. V. Sosunov、L. S. Viktorova、Yu. S. Skoblov

  DOI：10.1134/s1068162007050056

  日期：2007.9

  Isosteric triphosphonate derivatives of 2',3'-dideoxy-2',3'-didehydroadenosine and 3'-deoxy-2',3'-didehydrothymidine and their beta,gamma-substituted analogues were synthesized. Their substrate properties toward a number of reverse transcriptases of the human immunodeficiency and avian myeloblastosis viruses, human DNA polymerases alpha and beta, and the Klenow fragment of Escherichia coli DNA polymerase I were studied.