(2R,5R)-1-[2,5-Dihydro-5-(phosphonomethoxy)-2-furanyl]-5-chlorouracil | 959340-30-8

• 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,5R)-1-[2,5-Dihydro-5-(phosphonomethoxy)-2-furanyl]-5-chlorouracil
• 英文别名: [(2R,5R)-5-(5-chloro-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]oxymethylphosphonic acid
• CAS: 959340-30-8
• 化学式: C₉H₁₀ClN₂O₇P
• 分子量: 324.614
• InChiKey: SPMKPZJDJXALQY-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氯甲基碳酸异丙酯 、 (2R,5R)-1-[2,5-Dihydro-5-(phosphonomethoxy)-2-furanyl]-5-chlorouracil 在 吡啶 、 四丁基溴化铵 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 环己烷 为溶剂， 以8.2 %的产率得到((((((2R,5R)-5-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)oxy)methyl)phosphoryl)bis(oxy))bis(methylene) diisopropyl bis(carbonate)
  参考文献：
  名称：

  CYCLOPENTENE-OXYMETHYLENE PHOSPHONAMIDATES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS

  摘要：

  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.

  公开号：

  WO2024107859A1
• 作为产物：
  描述：

  (2R,5R)-1-[2,5-Dihydro-5-(dimethoxy-phosphinyl)methoxy-2-furanyl]-5-chlorouracil 在 三甲基溴硅烷 、 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,5R)-1-[2,5-Dihydro-5-(phosphonomethoxy)-2-furanyl]-5-chlorouracil
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.10.038

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.
• 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.