5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione | 195971-22-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione
• 英文别名: 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-[(8-methyl-2-oxo-4H-1,3,2λ5-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 195971-22-3
• 化学式: C₁₇H₁₈FN₂O₈P
• 分子量: 428.311
• InChiKey: DBYXXPDVBXGZQA-XDBDKROASA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione 在 RPMI culture medium 作用下， 反应 1.5h， 生成 3-甲基水杨醇 、 [(2R,3S,5R)-5-(5-氟-2,4-二氧代嘧啶-1-基)-3-羟基四氢呋喃-2-基]磷酸二氢甲酯
  参考文献：
  名称：

  Lorey, Martina; Meier, Chris; De Clercq, Eric, Nucleosides and Nucleotides, 1997, vol. 16, # 5-6, p. 789 - 792

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基水杨酸 在 吡啶 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 乙醚 为溶剂， 反应 2.67h， 生成 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Cyclo-saligenyl-5-fluoro-2′-deoxyuridinemonophosphate (cycloSal-FdUMP) — A New Prodrug Approach for FdUMP

  摘要：

  The synthesis of cycloSal-FdUMP 3a-d as a new prodrug approach for FdU 1 is described. Phosphotriesters 3 release the FdUMP 2 selectively by a controlled, chemically induced tandem reaction in hydrolysis studies. The biological activity (IC50) of cycloSal-phosphotriesters 3 was evaluated in FM3A/O cells and FM3A/TK- cells.

  DOI：

  10.1080/07328319708006177

文献信息

• Interaction of <i>cyclo</i>Sal-Pronucleotides with Cholinesterases from Different Origins. A Structure−Activity Relationship
  作者：Chris Meier、Christian Ducho、Ulf Görbig、Robert Esnouf、Jan Balzarini

  DOI：10.1021/jm031032a

  日期：2004.5.1

  A large number of cycloSal-nucleotide triesters 1-49 have been studied concerning their ability to inhibit cholinesterases of different origins as well as to inhibit HIV replication in cell culture. It was shown that none of the triesters showed inhibitory effects against human acetylcholinesterase (AChE; isolated enzyme) as well as against AChE from beef erythrocytes and calf serum. In contrast, inhibition of butyrylcholinesterase (BChE) has been observed for some triesters in human and mouse serum. cycloSal pronucleotides showed strong competitive inhibition with respect to the substrate acetylcholine chloride (K-i/K-m: similar to2 x 10(-5)) and acted by time-dependent irreversible inhibition of the human serum BChE. Detailed studies demonstrated that the inhibitory effect against BChE is dependent on the nucleoside analogue, the substitution pattern of the cycloSal-moiety, and particularly on the stereochemistry at the phosphorus atom. Structural requirements to avoid the inhibition of BChE by cycloSal-nucleotide triesters have been elucidated in the reported study.
• <i>Cyclo</i>-saligenyl-5-fluoro-2′-deoxyuridinemonophosphate (<i>cyclo</i>Sal-FdUMP) — A New Prodrug Approach for FdUMP
  作者：Martina Lorey、Chris Meier、Eric De Clercq、Jan Balzarini

  DOI：10.1080/07328319708006177

  日期：1997.7

  The synthesis of cycloSal-FdUMP 3a-d as a new prodrug approach for FdU 1 is described. Phosphotriesters 3 release the FdUMP 2 selectively by a controlled, chemically induced tandem reaction in hydrolysis studies. The biological activity (IC50) of cycloSal-phosphotriesters 3 was evaluated in FM3A/O cells and FM3A/TK- cells.
• Lorey, Martina; Meier, Chris; De Clercq, Eric, Nucleosides and Nucleotides, 1997, vol. 16, # 5-6, p. 789 - 792
  作者：Lorey, Martina、Meier, Chris、De Clercq, Eric、Balzarini, Jan

  DOI：——

  日期：——