cyclo-3-methylsaligenyl 3'-azido-2',3'-dideoxythymidine monophosphate | 195885-84-8

• 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: cyclo-3-methylsaligenyl 3'-azido-2',3'-dideoxythymidine monophosphate
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5S)-4-azido-5-[(8-methyl-2-oxo-4H-1,3,2λ5-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 195885-84-8
• 化学式: C₁₈H₂₀N₅O₇P
• 分子量: 449.36
• InChiKey: NENSOAFAVKYDHT-DOQABKHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cyclo-3-methylsaligenyl 3'-azido-2',3'-dideoxythymidine monophosphate 在 RPMI culture medium 作用下， 生成 3-甲基水杨醇 、 3'-azido-2',3'-dideoxythymidine monophosphate
  参考文献：
  名称：

  Meier, Chris; De Clercq, Eric; Balzarini, Jan, Nucleosides and Nucleotides, 1997, vol. 16, # 5-6, p. 793 - 796

  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 、 乙腈 为溶剂， 反应 16.33h， 生成 cyclo-3-methylsaligenyl 3'-azido-2',3'-dideoxythymidine monophosphate
  参考文献：
  名称：

  Nucleotide Delivery fromcycloSaligenyl-3′-azido-3′-deoxythymidine Monophosphates (cycloSal-AZTMP)

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<837::aid-ejoc837>3.0.co;2-7

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.
• Nucleotide Delivery fromcycloSaligenyl-3′-azido-3′-deoxythymidine Monophosphates (cycloSal-AZTMP)
  作者：Chris Meier、Eric De Clercq、Jan Balzarini

  DOI：10.1002/(sici)1099-0690(199805)1998:5<837::aid-ejoc837>3.0.co;2-7

  日期：1998.5
• Meier, Chris; De Clercq, Eric; Balzarini, Jan, Nucleosides and Nucleotides, 1997, vol. 16, # 5-6, p. 793 - 796
  作者：Meier, Chris、De Clercq, Eric、Balzarini, Jan

  DOI：——

  日期：——