9-<<<(diethoxyphosphinyl)methoxy>methoxy>methyl>adenine | 131853-13-9

• 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: 9-<<<(diethoxyphosphinyl)methoxy>methoxy>methyl>adenine
• 英文别名: 9-({[(diethoxyphosphinyl)methoxy]methoxy}methyl)adenine；9-[(Diethylphosphonomethoxy)methoxymethyl]adenine；9-(diethoxyphosphorylmethoxymethoxymethyl)purin-6-amine
• CAS: 131853-13-9
• 化学式: C₁₂H₂₀N₅O₅P
• 分子量: 345.295
• InChiKey: PAYVFOKLWBTLHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-<<<(diethoxyphosphinyl)methoxy>methoxy>methyl>adenine 在 三甲基溴硅烷 、 碳酸氢钠 作用下， 生成 9-<<(phosphonomethoxy)methoxy>methyl>adenine disodium salt
  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：

  sodium adeninate 、 (chloromethoxy)<(diethoxyphosphinyl)methoxy>methane 以 N,N-二甲基甲酰胺 为溶剂， 生成 9-<<<(diethoxyphosphinyl)methoxy>methoxy>methyl>adenine
  参考文献：
  名称：

  Kim, Choung Un; Misco, Peter F.; Luh, Bing Y., Heterocycles, 1990, vol. 31, # 9, p. 1571 - 1574

  摘要：

  DOI：

文献信息

• Phosphonate nucleoside analogs
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05693798A1

  公开（公告）日：1997-12-02

  Provided are compounds of the following formulae: A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## 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, hydroxyalkyl or alkanoyl and B is a purine or pyrimidine base. A 4'-phosphonomethoxytetrahydrofuranyl-1'-purine-pyrimidine of the formula ##STR2## wherein X and X' are the same or different and are hydrogen or alkyl, Y and Z are the same or 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.

  提供以下式子的化合物：公式为A的磷酸甲氧甲氧甲基嘌呤/嘧啶衍生物##STR1##其中X和X'相同或不同，是氢或烷基。R和R'相同或不同，是氢、烷基、羟基烷基或脂肪酰基，B是一种嘌呤或嘧啶碱基。公式为##STR2##其中X和X'相同或不同，是氢或烷基，Y和Z相同或不同，是氢、羟基或烷基，或Y+Z是烯烃、环氧化物或环丙基，B是一种嘌呤或嘧啶碱基。
• Nucleoside analogs
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05686611A1

  公开（公告）日：1997-11-11

  Provided are compounds of the following formulae: A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## 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, hydroxyalkyl or alkanoyl and B is a purine or pyrimidine base. A compound of formula (VI) ##STR2## wherein X is halogen, Y is S-phenyl, Se-phenyl or halogen and B is hypoxanthine, xanthine, guanine, 8-bromoguanine, 8-chloroguanine, 8-methylguanine, 8-thioguanine, 3-deazaguanine, purine, 2-aminopurine, 2,6-diaminopurine, adenine, 3-deazaadenine, 8-aminoguanine, 8-hydrazinoguanine, 8-hydroxyguanine, cytosine, 5-ethylcytosine, 5-methylcytosine, thymine, uracil, 5-chlorouracil, 5-bromouracil, 5-ethyluracil, 5-iodouracil, 5-propyluracil or 5-vinyluracil, 2-acetamido-6-diphenylcarbamoylpurine, 6-N-dimethylamino-methyladenine or 6-N-pivaloyladenine. A compound of formula (VII) ##STR3## wherein B is guanine, 8-guanine, 8-bromoguanine, 8-chloroguanine, 8-methylguanine, 8-thioguanine, 3-deazaguanine, 8-aminoguanine, 8-hydrazinoguanine, 8-hydroxyguanine, cytosine, 5-ethylcytosine, or 5-methylcytosine.

  提供以下化合物的公式：一种公式为##STR1##的磷酸甲氧甲氧甲基嘌呤/嘧啶衍生物，其中X和X'相同或不同，是氢或烷基；R和R'相同或不同，是氢、烷基、羟基烷基或酰基；B是嘌呤或嘧啶碱基。一种公式为##STR2##的化合物，其中X为卤素，Y为S-苯基、Se-苯基或卤素，B为嘧啶嘌呤、黄嘌呤、鸟嘌呤、8-溴鸟嘌呤、8-氯鸟嘌呤、8-甲基鸟嘌呤、8-硫鸟嘌呤、3-脱氮鸟嘌呤、嘌呤、2-氨基嘌呤、2,6-二氨基嘌呤、腺嘌呤、3-脱氮腺嘌呤、8-氨基鸟嘌呤、8-肼鸟嘌呤、8-羟基鸟嘌呤、胞嘧啶、5-乙基胞嘧啶、5-甲基胞嘧啶、胸腺嘧啶、尿嘧啶、5-氯尿嘧啶、5-溴尿嘧啶、5-乙基尿嘧啶、5-碘尿嘧啶、5-丙基尿嘧啶或5-乙烯基尿嘧啶、2-乙酰氨基-6-二苯基氨基嘌呤、6-N-二甲基氨基甲基腺嘌呤或6-N-皮酰基腺嘌呤。一种公式为##STR3##的化合物，其中B为鸟嘌呤、8-鸟嘌呤、8-溴鸟嘌呤、8-氯鸟嘌呤、8-甲基鸟嘌呤、8-硫鸟嘌呤、3-脱氮鸟嘌呤、8-氨基鸟嘌呤、8-肼鸟嘌呤、8-羟基鸟嘌呤、胞嘧啶、5-乙基胞嘧啶或5-甲基胞嘧啶。
• 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