6-methylamino-9-(2',3'-dideoxy-3'-fluoro-β-D-ribofuranosyl)purine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-methylamino-9-(2',3'-dideoxy-3'-fluoro-β-D-ribofuranosyl)purine
• 英文别名: 9-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)-6-(methylamino)-9H-purine；9-(2,3-dideoxy-3-fluoro-beta-D-erythro-pentofuranosyl)-6-(methylamino)-9H-purine；[(2R,3S,5R)-3-fluoro-5-[6-(methylamino)purin-9-yl]oxolan-2-yl]methanol
• 化学式: C₁₁H₁₄FN₅O₂
• 分子量: 267.263
• InChiKey: BDZVFPDFNFDGNG-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl methoxyalaninyl phosphorochloridate 、 6-methylamino-9-(2',3'-dideoxy-3'-fluoro-β-D-ribofuranosyl)purine 在 吡啶 、 叔丁基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到6-methylamino-9-(2',3'-dideoxy-3'-fluoro-β-D-ribofuranosyl)purine-5'-[phenyl-(methoxy-L-alaninyl)]phosphoramidate
  参考文献：
  名称：

  Phosphoramidate Protides of 2′,3′-Dideoxy-3′-fluoroadenosine and Related Nucleosides with Potent Activity Against HIV and HBV

  摘要：

  Syntheses of phosphoramidate protides of several 2',3'-dideoxy-3'-fluoroadenosine derivatives by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleoside against HIV and HBV. Especially marked was the improvement in potency of phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine against both HIV and HBV.

  DOI：

  10.1081/ncn-120025242
• 作为产物：
  描述：

  2',3'-dideoxy-3'-fluorouridine 、 6-甲基腺素 、 cellulose 以 甲醇 为溶剂， 以73%的产率得到6-methylamino-9-(2',3'-dideoxy-3'-fluoro-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  2',3'-dideoxy-3'-fluoro-purine ribonucleosides

  摘要：

  2',3'-二脱氧-3'-氟-(B-D-核糖呋喃基) 嘌呤核苷具有抑制乙型肝炎和HIV病毒感染的能力。

  公开号：

  US05663154A1

文献信息

• US5663154A
  申请人：——

  公开号：US5663154A

  公开（公告）日：1997-09-02
• [EN] THERAPEUTIC NUCLEOSIDES
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1993014103A1

  公开（公告）日：1993-07-22

  (EN) The present invention relates to certain novel 2',3'-dideoxy-3'-fluoro-purine nucleoside compounds, salts, esters and physiologically functional derivatives thereof, processes for their preparation, pharmaceutical formulations containing them and to the use of such compounds in therapy, particularly the treatment of prophylaxis of viral infections.(FR) La présente invention se rapporte à certains nouveaux nucléosides 2',3'-dideoxy-3'-fluoro-purine, à des sels, des esters et des dérivés physiologiquement fonctionnels de ceux-ci, à des procédés de préparation, aux formulations pharmaceutiques les contenant et à l'utilisation de ces composés en thérapie, notamment dans le traitement ou la prophylaxie d'infections virales.
• 2',3'-dideoxy-3'-fluoro-purine ribonucleosides
  申请人：Glaxo Wellcome Inc.

  公开号：US05663154A1

  公开（公告）日：1997-09-02

  2',3'-Dideoxy-3'-fluoro-(B-D-ribofuranosyl) purine nucleosides possessing the ability to inhibit hepatitis B and HIV viral infections.

  2',3'-二脱氧-3'-氟-(B-D-核糖呋喃基) 嘌呤核苷具有抑制乙型肝炎和HIV病毒感染的能力。
• Phosphoramidate Protides of 2′,3′-Dideoxy-3′-fluoroadenosine and Related Nucleosides with Potent Activity Against HIV and HBV
  作者：Kristjan S. Gudmundsson、Susan M. Daluge、Lance C. Johnson、Robert Jansen、Richard Hazen、Lynn D. Condreay、Christopher McGuigan

  DOI：10.1081/ncn-120025242

  日期：2003.10.1

  Syntheses of phosphoramidate protides of several 2',3'-dideoxy-3'-fluoroadenosine derivatives by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleoside against HIV and HBV. Especially marked was the improvement in potency of phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine against both HIV and HBV.