9-[3-C-(azidomethyl)-3-deoxy-β-D-ribofuranosyl]adenine | 180403-70-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-[3-C-(azidomethyl)-3-deoxy-β-D-ribofuranosyl]adenine
• 英文别名: (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-4-(azidomethyl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 180403-70-7
• 化学式: C₁₁H₁₄N₈O₃
• 分子量: 306.284
• InChiKey: YWYBWWBXDKZRTG-HUKYDQBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-[3-C-(azidomethyl)-3-deoxy-β-D-ribofuranosyl]adenine 在 吡啶 、 三苯基膦 作用下， 反应 1.5h， 以64%的产率得到(2R,3R,4S,5S)-4-Aminomethyl-2-(6-amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety

  摘要：

  In this paper we investigated the influence on affinity, selectivity and intrinsic activity upon modification of the adenosine agonist scaffold at the 3- and 5'-positions of the ribofuranosyl moiety and the 2- and N-6-positions of the purine base. This resulted in the synthesis of various analogues, that is, 3-12 and 24-33, with good hA(3)AR selectivity and moderate-to-high affinities (as in 32, K-i = 27 nM). Interesting was the ability to tune the intrinsic activity depending on the substituent introduced at the 3'-position. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.044
• 作为产物：
  描述：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 sodium azide 、 硫酸 、 氨 、 四氯化锡 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 305.0h， 生成 9-[3-C-(azidomethyl)-3-deoxy-β-D-ribofuranosyl]adenine
  参考文献：
  名称：

  Synthesis and antiviral activity of 3′-C-branched-3′-deoxy analogues of adenosine

  摘要：

  The synthesis of some 3'-C-branched-3'-deoxy adenine nucleosides is described, Starting from the known 3-deoxy-3-C-(hydroxymethyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (1), a versatile glycosylating agent, namely 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-(mesyloxymethyl)-beta-D-ribofuranose (6), was prepared in three steps, Condensation of the latter with bis(trimethysilylated) N-6-benzoyladenine in the presence of tin(IV) chloride gave the N-9-beta-nucleoside 7. Compound 7 was converted into (i) 9-[3-C-(azidomethyl)-3-deoxy-beta-D-ribofuranosyl]adenine (10), (ii) 9-[3-C-(azidomethyl)-2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl]adenine (14) and 9-[2-azido-3-C-(azidomethyl)-2,3-dideoxy-beta-D-arabinofuranosyl]adenine (15), and (iii) 9-[3-deoxy-2-O,3-C-(methylene)-beta-D-ribofuranosyl]adenine (16). None of the tested nucleosides showed marked cytostatic or antiviral activity in vitro. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00028-6