N⁶-nonanoyl-8-azaadenine | 4471-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: N⁶-nonanoyl-8-azaadenine
• 英文别名: nonanoic acid 1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamide；6-Nonanamido-8-aza-purin；N-Nonanoyl-8-azaadenin；N-nonanoyl-8-azaadenine；N-(2H-triazolo[4,5-d]pyrimidin-7-yl)nonanamide
• CAS: 4471-88-9
• 化学式: C₁₃H₂₀N₆O
• 分子量: 276.341
• InChiKey: UHMBRXZSOLYKQZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 N⁶-nonanoyl-8-azaadenine 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 、 、
  参考文献：
  名称：

  High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries

  摘要：

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

  DOI：

  10.1021/jo061885l

文献信息

• Modifizierte Oligonukleotide, deren Herstellung sowie deren Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0680969A2

  公开（公告）日：1995-11-08

  Die Erfindung betrifft neue modifizierte Oligonukleotide, die mindestens eine 8-Azapurinbase aufweisen und stabilere Hybdridisierungskomplexe mit Nukleinsäuren bilden; Verfahren zu deren Herstellung sowie deren Verwendung als Inhibitoren der Genexpression, als Sonden zum Nachweis von Nukleinsäuren, als Hilfsmittel in der Molekularbiologie und als Arzneimittel oder Diagnostikum.

  本发明涉及新的修饰寡核苷酸，这种寡核苷酸至少有一个 8-氮杂嘌呤碱基，能与核酸形成更稳定的杂交复合物； 其制备方法及其作为基因表达抑制剂、核酸检测探针、分子生物学辅助剂和药物或诊断剂的用途。
• Enhancement of Nucleoside Cytotoxicity through Nucleotide Prodrugs
  作者：Jerry D. Rose、William B. Parker、Hitoshi Someya、Sue C. Shaddix、John A. Montgomery、John A. Secrist

  DOI：10.1021/jm020107s

  日期：2002.9.1

  A common reason for the lack of cytotoxicity of certain nucleosides is thought to be their inability to be initially activated to the monophosphate level by a nucleoside kinase or other activating enzyme. In a search for other nucleosides that might be worthwhile anticancer agents, we have begun to examine the utilization of monophosphate prodrugs in order to explore whether any enhanced cytotoxicity might be found for the prodrugs of candidate nucleosides that have little or no cytotoxicity. To that end, 5'-bis(pivaloyloxymethyl) phosphate prodrugs of two weakly cytotoxic compounds, 8-aza-2'-deoxyadenosine (5) and 8-bromo-2'-deoxyadenosine (9), have been prepared. These prodrugs (8 and 12) were examined for their cytotoxicity in CEM cells and were found to possess significantly enhanced cytotoxicity when compared with the corresponding parent nucleosides. Further cell culture experiments were conducted to gain insight into the mechanisms of cytotoxicity of these two prodrugs, and those data are reported.
• US6066720A
  申请人：——

  公开号：US6066720A

  公开（公告）日：2000-05-23
• High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries
  作者：Brett C. Bookser、Nicholas B. Raffaele

  DOI：10.1021/jo061885l

  日期：2007.1.1

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.