2-(acetylamino)-6-chloro-9-<(vinyloxy)methyl>purine | 134361-23-2

• 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-(acetylamino)-6-chloro-9-<(vinyloxy)methyl>purine
• 英文别名: 2-Acetamido-6-chloro-9-(vinyloxymethyl)purine；N-[6-chloro-9-(ethenoxymethyl)purin-2-yl]acetamide
• CAS: 134361-23-2
• 化学式: C₁₀H₁₀ClN₅O₂
• 分子量: 267.675
• InChiKey: WHEFRFHGHCYYJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(acetylamino)-6-chloro-9-<(vinyloxy)methyl>purine 在 盐酸 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 9-<(2-hydroxy-1-methoxyethoxy)methyl>guanine
  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-氨基-6-氯嘌呤 在 sodium periodate 、 碳酸氢钠 作用下， 反应 41.0h， 生成 2-(acetylamino)-6-chloro-9-<(vinyloxy)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

• Nucleoside analogs
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE ACADEMY OF SCIENCES OF THE CZECH REPUBLIC

  公开号：EP0398231A2

  公开（公告）日：1990-11-22

  Compounds of the following formulas which have anti-tumor and anti-viral activity and are especially useful in treating viral infections, their compositions and use. A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroyalkyl or R"CO-where R" is an alkyl and B is a purine or pyrimidine base. A 4 -phosphonomethoxytetrahydrofuranyl-1 -purine-pyrimidine of the formula wherein X and X are the same or different and are hydrogen or alkyl, Y and Z are the same of different and are hydrogen hydroxyl or alkyl or Y + Z is an alkenyl, an epoxide or cyclopropyl, and B is a purine or pyrimidine base.

  具有抗肿瘤和抗病毒活性，尤其适用于治疗病毒感染的下列配方的化合物、其组成和用途。 式中的磷酰甲氧基甲基嘌呤/嘧啶衍生物 其中 X 和 X'相同或不同，且为氢或烷基。 R和R'相同或不同，且为氢、烷基、氢烷基或R "CO-其中R "为烷基，B为嘌呤或嘧啶碱。 式中的 4-膦酰甲氧基四氢呋喃-1-嘌呤嘧啶 其中 X 和 X 是相同或不同的，并且是氢或烷基、 Y 和 Z 相同或不同，且为氢羟基或烷基，或 Y + Z 为烯基、环氧化物或环丙基，以及 B 是嘌呤或嘧啶碱。
• KIM, CHOUNG UN;MISCO, PETER F.;LUH, BING YU;HITCHCOCK, MICHAEL J. M.;GHAZ+, J. MED. CHEM., 34,(1991) N, C. 2286-2294
  作者：KIM, CHOUNG UN、MISCO, PETER F.、LUH, BING YU、HITCHCOCK, MICHAEL J. M.、GHAZ+

  DOI：——

  日期：——
• US5696265A
  申请人：——

  公开号：US5696265A

  公开（公告）日：1997-12-09
• US5686611A
  申请人：——

  公开号：US5686611A

  公开（公告）日：1997-11-11
• US5688778A
  申请人：——

  公开号：US5688778A

  公开（公告）日：1997-11-18