1-Deazapurine riboside | 5128-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Deazapurine riboside
• 英文别名: 3-β-D-ribofuranosyl-3H-imidazo<4,5-b>pyridine；1-imidazo[4,5-b]pyridin-3-yl-β-D-1-deoxy-ribofuranose；3-<β-D-Ribofuranosyl>-imidazo<4,5-b>pyridin；3-β-D-Ribofuranosyl-3H-imidazo<4.5-b>pyridin；3-(β-D-Ribofuranosyl)-imidazo<4,5-b>pyridin；3-β-D-Ribofuranosylimidazo<4,5-b>pyridin；3H-Imidazo[4,5-b]pyridine, 3-beta-D-ribofuranosyl-；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-imidazo[4,5-b]pyridin-3-yloxolane-3,4-diol
• CAS: 5128-01-8
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: JVODRKOKQFRWIN-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 氨 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 60.0h， 生成 1-Deazapurine riboside
  参考文献：
  名称：

  Gupta, P. K.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 9, p. 817 - 819

  摘要：

  DOI：

文献信息

• Deaza Analogues of Adenosine as Inhibitors of Blood Platelet Aggregation
  作者：Ippolito Antonini、Gloria Cristalli、Palmarisa Franchetti、Mario Grifantini、Sante Martelli、Franco Petrelli

  DOI：10.1002/jps.2600730319

  日期：1984.3

  A number of deaza analogues of adenosine were prepared and tested as inhibitors of platelet aggregation induced by ADP and collagen to investigate the structure-activity relationships in this class of nucleoside analogues. The results showed that the presence of a 6-amino group and nitrogen atoms at positions 3 and 7 of the purine moiety are required for inhibitory activity.

  制备了许多腺苷的脱氮杂类似物，并作为由ADP和胶原诱导的血小板聚集的抑制剂进行了测试，以研究此类核苷类似物中的构效关系。结果表明，抑制活性需要在嘌呤部分的3位和7位存在6-氨基和氮原子。
• 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.
• Gupta, P. K.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. <B> 20, # 9, p. 817 - 819
  作者：Gupta, P. K.、Bhakuni, D. S.

  DOI：——

  日期：——