9-[(1R,4S,5R)-5-benzoyl-4-benzoylmethyl-2-cyclohexenyl]adenine | 262372-13-4

• 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: 9-[(1R,4S,5R)-5-benzoyl-4-benzoylmethyl-2-cyclohexenyl]adenine
• 英文别名: [(1S,4R,6R)-4-(6-aminopurin-9-yl)-6-benzoyloxycyclohex-2-en-1-yl]methyl benzoate
• CAS: 262372-13-4
• 化学式: C₂₆H₂₃N₅O₄
• 分子量: 469.5
• InChiKey: VBGIVNVRDLGENV-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-[(1R,4S,5R)-5-benzoyl-4-benzoylmethyl-2-cyclohexenyl]adenine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以77%的产率得到9-[(1R,4S,5R)-5-hydroxy-4-hydroxymethyl-2-cyclohexenyl]adenine
  参考文献：
  名称：

  The Cyclohexene Ring System as a Furanose Mimic:  Synthesis and Antiviral Activity of Both Enantiomers of Cyclohexenylguanine

  摘要：

  Both enantiomers of cyclohexenylguanine were synthesized in a stereospecific way starting from the same starting material: R-(-)-carvone. Both compounds showed potent-and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). The binding of both cyclohexene nucleosides in the active site of HSV-1 thymidine kinase was investigated, and a model for the binding of both enantiomers is proposed. The amino acids involved in binding of the optical antipodes are the same, but the interaction energy of both enantiomers is slightly different. This may be attributed to the interaction of the secondary hydroxyl function of the nucleoside analogues with Glu-225. Structural analysis has demonstrated the flexibility of the cyclohexenyl system, and this may be considered as an important conformational characteristic explaining the potent antiviral activity.

  DOI：

  10.1021/jm991171l
• 作为产物：
  描述：

  (1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)cyclohexan-1-ol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 cerium(III) chloride 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 43.5h， 生成 9-[(1R,4S,5R)-5-benzoyl-4-benzoylmethyl-2-cyclohexenyl]adenine
  参考文献：
  名称：

  The Cyclohexene Ring System as a Furanose Mimic:  Synthesis and Antiviral Activity of Both Enantiomers of Cyclohexenylguanine

  摘要：

  Both enantiomers of cyclohexenylguanine were synthesized in a stereospecific way starting from the same starting material: R-(-)-carvone. Both compounds showed potent-and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). The binding of both cyclohexene nucleosides in the active site of HSV-1 thymidine kinase was investigated, and a model for the binding of both enantiomers is proposed. The amino acids involved in binding of the optical antipodes are the same, but the interaction energy of both enantiomers is slightly different. This may be attributed to the interaction of the secondary hydroxyl function of the nucleoside analogues with Glu-225. Structural analysis has demonstrated the flexibility of the cyclohexenyl system, and this may be considered as an important conformational characteristic explaining the potent antiviral activity.

  DOI：

  10.1021/jm991171l

文献信息

• CARBOCYCLIC NUCLEOSIDES AND PROCESS FOR OBTAINING SUCH
  申请人：Stichting REGA V.Z.W.

  公开号：EP1210347B1

  公开（公告）日：2004-06-23
• The Cyclohexene Ring System as a Furanose Mimic:  Synthesis and Antiviral Activity of Both Enantiomers of Cyclohexenylguanine
  作者：Jing Wang、Matheus Froeyen、Chris Hendrix、Graciela Andrei、Robert Snoeck、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jm991171l

  日期：2000.2.1

  Both enantiomers of cyclohexenylguanine were synthesized in a stereospecific way starting from the same starting material: R-(-)-carvone. Both compounds showed potent-and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). The binding of both cyclohexene nucleosides in the active site of HSV-1 thymidine kinase was investigated, and a model for the binding of both enantiomers is proposed. The amino acids involved in binding of the optical antipodes are the same, but the interaction energy of both enantiomers is slightly different. This may be attributed to the interaction of the secondary hydroxyl function of the nucleoside analogues with Glu-225. Structural analysis has demonstrated the flexibility of the cyclohexenyl system, and this may be considered as an important conformational characteristic explaining the potent antiviral activity.