[(1S,4R,6R)-4-(2-amino-6-chloropurin-9-yl)-6-benzoyloxycyclohex-2-en-1-yl]methyl benzoate | 262372-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S,4R,6R)-4-(2-amino-6-chloropurin-9-yl)-6-benzoyloxycyclohex-2-en-1-yl]methyl benzoate
• CAS: 262372-14-5
• 化学式: C₂₆H₂₂ClN₅O₄
• 分子量: 503.945
• InChiKey: NYIYSSXLTDVHPE-SLFFLAALSA-N

物化性质

• 沸点：
  724.7±70.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 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：

  [(1S,4R,6R)-4-(2-amino-6-chloropurin-9-yl)-6-benzoyloxycyclohex-2-en-1-yl]methyl benzoate 在 氨 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 (1R,4S,5R)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine
  参考文献：
  名称：

  （D）-和（L）-环己烯醇-G，一类新的抗病毒剂：合成，构象分析，分子建模和生物活性

  摘要：

  从（R）-香芹酮开始对映选择性地合成（D）-和（L）-环己烯基-G。两者均显示有效和选择性的抗疱疹病毒活性（HSV-1，HSV-2，VZV，CMV）。分子建模表明，两种异构体均以高能构象结合在HSV-1胸苷激酶的活性位点上，且碱基部分位于赤道位置。据信，环己烯环的柔韧性对其抗病毒活性至关重要。

  DOI：

  10.1081/ncn-100002360
• 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 [(1S,4R,6R)-4-(2-amino-6-chloropurin-9-yl)-6-benzoyloxycyclohex-2-en-1-yl]methyl benzoate
  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

• (D)- AND (L)-CYCLOHEXENYL-G, A NEW CLASS OF ANTIVIRAL AGENTS: SYNTHESIS, CONFORMATIONAL ANALYSIS, MOLECULAR MODELING, AND BIOLOGICAL ACTIVITY
  作者：J. Wang、M. Froeyen、C. Hendrix、C. Andrei、R. Snoeck、E. Lescrinier、E. De Clercq、P. Herdewijn

  DOI：10.1081/ncn-100002360

  日期：2001.3.31

  (D)- and (L)-cyclohexeneyl-G were synthesized enantioselectively starting from (R)-carvone. Both show potent and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). Molecular modeling demonstrates that both isomers are bound in the active site of HSV-1 thymidine kinase in a high-energy conformation with the base moiety orienting in an equatorial position. It is believed that the flexibility

  从（R）-香芹酮开始对映选择性地合成（D）-和（L）-环己烯基-G。两者均显示有效和选择性的抗疱疹病毒活性（HSV-1，HSV-2，VZV，CMV）。分子建模表明，两种异构体均以高能构象结合在HSV-1胸苷激酶的活性位点上，且碱基部分位于赤道位置。据信，环己烯环的柔韧性对其抗病毒活性至关重要。
• 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.