5-nitro-7-amino-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine | 306275-38-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 5-nitro-7-amino-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
• 英文别名: 2-nitro-1-deazaadenosine triacetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(7-amino-5-nitroimidazo[4,5-b]pyridin-3-yl)oxolan-2-yl]methyl acetate
• CAS: 306275-38-7
• 化学式: C₁₇H₁₉N₅O₉
• 分子量: 437.366
• InChiKey: HSYGWQNXNJXTEM-BNGXUDDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  191
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-nitro-7-amino-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 在 甲醇 、 potassium cyanide 作用下， 反应 5.0h， 以92%的产率得到2-nitro-1-deazaadenosine
  参考文献：
  名称：

  2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes

  摘要：

  The influence of nitro substituents on the properties of adenosine and 1-deazaadenosine was studied. Combination of a nitro group at the 2-position with several N-6 substituents such as cyclopentyl and m-iodobenzyl gave a series of analogues with good adenosine receptor affinity, showing directable selectivity for the A(1), A(2A) and A(3) adenosine receptor subtypes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00415-7
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(5,7-dinitro-imidazo[4,5-b]pyridin-3-yl)-tetrahydro-furan-3-yl ester 在 sodium azide 、 三苯基膦 作用下， 以 水 、 溶剂黄146 为溶剂， 以51%的产率得到5-nitro-7-amino-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Mild and regioselective nitration of 1-deazapurine nucleosides using TBAN/TFAA

  摘要：

  To obtain selectively functionalized 1-deazapurine nucleosides, the nitrating mixture tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) has been studied. This mixture demonstrated several merits: the use of an easy to handle reagent, mild reaction conditions and high selectivity for nitration in the pyridine ring. Nitration occurred at the alpha or beta-position with respect to the pyridine nitrogen atom, depending on the substituents in the ring. Electron withdrawing substituents in the pyridine ring showed a positive effect on this nitration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02073-0

文献信息

• Synthesis and Stability Studies of 2′,3′,5′-tri-<b><i>O</i></b>-Acetyl-2-Amino(-N^{<b><i>6</i></b>}-Cyclopentyl)-1-Deazaadenosines
  作者：Sauro Vittori、Ram Chandra Mishra、Diego Dal Ben、Dhuldeo Kachare、Catia Lambertucci、Rosaria Volpini、Gloria Cristalli

  DOI：10.1080/15257770701542231

  日期：2007.11.26

  In this article, we report on the synthesis of 2',3',5'-tri-O-acetyl-2-amino-1-deazaadenosine and of 2',3',5'-tri-O-acetyl-2-amino-N(6)-cyclopentyl-1-deazaadenosine, which are very versatile intermediates for the preparation of 2-substituted 1-deazaadenosine derivatives. The two synthesized compounds showed to be quite unstable, with the N(6)-substituted derivatives being less stable than the N(6)-unsubstituted counterpart, according to the calculated HOMO-LUMO energy gap. Stability studies were performed through HPLC-MS analysis.