2-amino-6-chloro-9-<<2-phenylselenyl)ethoxy>methyl>purine | 134361-21-0

• 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: 2-amino-6-chloro-9-<<2-phenylselenyl)ethoxy>methyl>purine
• 英文别名: 2-amino-6-chloro-9-[(2-phenylselenyl)ethoxymethyl]purine；6-Chloro-9-(2-phenylselanylethoxymethyl)purin-2-amine
• CAS: 134361-21-0
• 化学式: C₁₄H₁₄ClN₅OSe
• 分子量: 382.711
• InChiKey: HQLOMCNSUWLMLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-9-<<2-phenylselenyl)ethoxy>methyl>purine 在 sodium periodate 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 59.0h， 生成 N-[6-Chloro-9-(2-hydroxy-1-methoxy-ethoxymethyl)-9H-purin-2-yl]-acetamide
  参考文献：
  名称：

  A new class of acyclic phosphonate nucleotide analogs: Phosphonate isosteres of acyclovir and ganciclovir monophosphates as antiviral agents

  摘要：

  Novel phosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates (20 and 32) were found to be potent and selective antiherpesvirus agents. In the series of phosphonate analogues of ACV monophosphate, only the guanine analogue 20 exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogues. The phosphonate isostere of ACV monophosphate (20) was more effective than ACV in the HSV-1 infected mouse model. The 3'-carba analogues of 9-[3-hydroxy-2-(phosphonomethoxy)propyl]purines/pyrimidines (adenine, HPMPA; guanine, HPMPG; cytosine, HPMPC) are devoid of antiherpesvirus activity. This result confirms that the beta-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses.

  DOI：

  10.1021/jm00111a052
• 作为产物：
  描述：

  2-(phenylselenyl)ethanol 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-amino-6-chloro-9-<<2-phenylselenyl)ethoxy>methyl>purine
  参考文献：
  名称：

  A new class of acyclic phosphonate nucleotide analogs: Phosphonate isosteres of acyclovir and ganciclovir monophosphates as antiviral agents

  摘要：

  Novel phosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates (20 and 32) were found to be potent and selective antiherpesvirus agents. In the series of phosphonate analogues of ACV monophosphate, only the guanine analogue 20 exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogues. The phosphonate isostere of ACV monophosphate (20) was more effective than ACV in the HSV-1 infected mouse model. The 3'-carba analogues of 9-[3-hydroxy-2-(phosphonomethoxy)propyl]purines/pyrimidines (adenine, HPMPA; guanine, HPMPG; cytosine, HPMPC) are devoid of antiherpesvirus activity. This result confirms that the beta-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses.

  DOI：

  10.1021/jm00111a052

文献信息

• A new class of acyclic phosphonate nucleotide analogs: Phosphonate isosteres of acyclovir and ganciclovir monophosphates as antiviral agents
  作者：Choung Un Kim、Peter F. Misco、Bing Yu Luh、Michael J. M. Hitchcock、Ismail Ghazzouli、John C. Martin

  DOI：10.1021/jm00111a052

  日期：1991.7

  Novel phosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates (20 and 32) were found to be potent and selective antiherpesvirus agents. In the series of phosphonate analogues of ACV monophosphate, only the guanine analogue 20 exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogues. The phosphonate isostere of ACV monophosphate (20) was more effective than ACV in the HSV-1 infected mouse model. The 3'-carba analogues of 9-[3-hydroxy-2-(phosphonomethoxy)propyl]purines/pyrimidines (adenine, HPMPA; guanine, HPMPG; cytosine, HPMPC) are devoid of antiherpesvirus activity. This result confirms that the beta-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses.