(1S,4R)-4-(6-chloro-9H-purin-9-yl)-1-methylcyclopent-2-en-1-ol | 1142816-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (1S,4R)-4-(6-chloro-9H-purin-9-yl)-1-methylcyclopent-2-en-1-ol
• 英文别名: (1S,4R)-4-(6-chloro-9H-purin-9-yl)-1-methyl-cyclopent-2-enol；(1S,4R)-4-(6-chloropurin-9-yl)-1-methylcyclopent-2-en-1-ol
• CAS: 1142816-42-9
• 化学式: C₁₁H₁₁ClN₄O
• 分子量: 250.688
• InChiKey: MFYSLMKCBMLGRF-WRWORJQWSA-N

物化性质

• 沸点：
  451.1±55.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4-(6-chloro-9H-purin-9-yl)-1-methylcyclopent-2-en-1-ol 在 三甲基溴硅烷 、 氨 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 8.67h， 生成 ((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-methylcyclopent-2-enyloxy)methylphosphonic acid diammonium salt
  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：

  (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol 在 cerium(III) chloride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 (1S,4R)-4-(6-chloro-9H-purin-9-yl)-1-methylcyclopent-2-en-1-ol
  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

文献信息

• Design, synthesis, and anti-HIV activity of 4′-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors
  作者：Constantine G. Boojamra、Jay P. Parrish、David Sperandio、Ying Gao、Oleg V. Petrakovsky、Sharon K. Lee、David Y. Markevitch、Jennifer E. Vela、Genevieve Laflamme、James M. Chen、Adrian S. Ray、Abraham C. Barron、Mark L. Sparacino、Manoj C. Desai、Choung U. Kim、Tomas Cihlar、Richard L. Mackman

  DOI：10.1016/j.bmc.2008.12.028

  日期：2009.2

  A diphosphate of a novel cyclopentyl based nucleoside phosphonate with potent inhibition of HIV reverse transcriptase (RT) (20, IC(50) = 0.13 mu M) has been discovered. In cell culture the parent phosphonate diacid 9 demonstrated antiviral activity EC(50) = 16 mu M, within two-fold of GS-9148, a prodrug of which is currently under clinical investigation, and within 5-fold of tenofovir (PMPA). In vitro cellular metabolism studies using 9 confirmed that the active diphosphate metabolite is produced albeit at a lower efficiency relative to GS-9148. (C) 2009 Elsevier Ltd. All rights reserved.