1-(guanin-9-yl)methyl-2-oxo-3-oxabicyclo[3.1.0]hexane | 172154-29-9

• 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: 1-(guanin-9-yl)methyl-2-oxo-3-oxabicyclo[3.1.0]hexane
• 英文别名: 2-amino-9-[(2-oxo-3-oxabicyclo[3.1.0]hexan-1-yl)methyl]-1H-purin-6-one
• CAS: 172154-29-9
• 化学式: C₁₁H₁₁N₅O₃
• 分子量: 261.24
• InChiKey: NIASWECSZXYBDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(guanin-9-yl)methyl-2-oxo-3-oxabicyclo[3.1.0]hexane 在 sodium tetrahydroborate 、 水 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-{[cis-1,2-bis(hydroxymethyl)cyclopropyl]methyl}-3,9-dihydro-9-oxo-6-phenyl-5H-imidazo[1,2-a]purine
  参考文献：
  名称：

  Synthesis and biological activity of tricyclic analogues of 9-{[cis-1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl}guanine

  摘要：

  The base moiety of the potent antiherpetic agent 9-{[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl}guanine 3 was transformed into that of the tricyclic 3,9-dihydro-9-oxo-6-R-5H-imidazo[1,2-a]purine system. The tricyclic analogues 5a-d were evaluated for their activity against herpes viruses as well as for cytostatic activity against HSV-1 thymidine kinase (TK) gene-transduced human osteosarcoma tumor cells. Marked activity was found against VZV. The 6-phenyl-substituted fluorescent analogues 5c and d were comparable to that of parent 3 in activity against the VZV strain YS and were 3-fold less active against the VZV strain OKA. The compounds 5a-d also showed marked activity against HSV-1 (KOS) and HSV-2 (G)-against the former generally approximately comparable to that of acyclovir la and one order of magnitude lower than 3; against the latter comparable to that of I a and approximately 6- to 30-fold lower than that of 3. The most pronounced cytostatic activity (5-fold lower than that of 3) was exhibited by compounds 5c and d. Tricyclic analogues with pseudosugar moieties are intrinsically bio-active. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.014
• 作为产物：
  描述：

  1-hydroxymethyl-2-oxo-3-oxabicyclo[3.1.0]hexane 在 4-二甲氨基吡啶 甲酸 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(guanin-9-yl)methyl-2-oxo-3-oxabicyclo[3.1.0]hexane
  参考文献：
  名称：

  Synthesis and biological activity of tricyclic analogues of 9-{[cis-1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl}guanine

  摘要：

  The base moiety of the potent antiherpetic agent 9-{[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl}guanine 3 was transformed into that of the tricyclic 3,9-dihydro-9-oxo-6-R-5H-imidazo[1,2-a]purine system. The tricyclic analogues 5a-d were evaluated for their activity against herpes viruses as well as for cytostatic activity against HSV-1 thymidine kinase (TK) gene-transduced human osteosarcoma tumor cells. Marked activity was found against VZV. The 6-phenyl-substituted fluorescent analogues 5c and d were comparable to that of parent 3 in activity against the VZV strain YS and were 3-fold less active against the VZV strain OKA. The compounds 5a-d also showed marked activity against HSV-1 (KOS) and HSV-2 (G)-against the former generally approximately comparable to that of acyclovir la and one order of magnitude lower than 3; against the latter comparable to that of I a and approximately 6- to 30-fold lower than that of 3. The most pronounced cytostatic activity (5-fold lower than that of 3) was exhibited by compounds 5c and d. Tricyclic analogues with pseudosugar moieties are intrinsically bio-active. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.014

文献信息

• Synthesis and biological activity of tricyclic analogues of 9-{[cis-1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl}guanine
  作者：Tomasz Ostrowski、Bozenna Golankiewicz、Erik De Clercq、Jan Balzarini

  DOI：10.1016/j.bmc.2006.01.014

  日期：2006.5

  The base moiety of the potent antiherpetic agent 9-[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl}guanine 3 was transformed into that of the tricyclic 3,9-dihydro-9-oxo-6-R-5H-imidazo[1,2-a]purine system. The tricyclic analogues 5a-d were evaluated for their activity against herpes viruses as well as for cytostatic activity against HSV-1 thymidine kinase (TK) gene-transduced human osteosarcoma tumor cells. Marked activity was found against VZV. The 6-phenyl-substituted fluorescent analogues 5c and d were comparable to that of parent 3 in activity against the VZV strain YS and were 3-fold less active against the VZV strain OKA. The compounds 5a-d also showed marked activity against HSV-1 (KOS) and HSV-2 (G)-against the former generally approximately comparable to that of acyclovir la and one order of magnitude lower than 3; against the latter comparable to that of I a and approximately 6- to 30-fold lower than that of 3. The most pronounced cytostatic activity (5-fold lower than that of 3) was exhibited by compounds 5c and d. Tricyclic analogues with pseudosugar moieties are intrinsically bio-active. (c) 2006 Elsevier Ltd. All rights reserved.