2-Amino-9-[(1R,4S)-4-(8-methyl-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-cyclopent-2-enyl]-1,9-dihydro-purin-6-one

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2-Amino-9-[(1R,4S)-4-(8-methyl-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-cyclopent-2-enyl]-1,9-dihydro-purin-6-one
• 英文别名: 2-amino-9-[(1R,4S)-4-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]cyclopent-2-en-1-yl]-1H-purin-6-one；2-amino-9-[(1R,4S)-4-[(8-methyl-2-oxo-4H-1,3,2λ5-benzodioxaphosphinin-2-yl)oxymethyl]cyclopent-2-en-1-yl]-1H-purin-6-one
• 化学式: C₁₉H₂₀N₅O₅P
• 分子量: 429.372
• InChiKey: LHGAUFVMLCRJDH-WSVRYRSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-卡巴韦 在 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 生成 2-Amino-9-[(1R,4S)-4-(8-methyl-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-cyclopent-2-enyl]-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Interaction of cycloSal-Pronucleotides with Cholinesterases from Different Origins. A Structure−Activity Relationship

  摘要：

  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.

  DOI：

  10.1021/jm031032a