2-nitro-1-deazaadenosine | 306275-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-nitro-1-deazaadenosine
• 英文别名: (2R,3R,4S,5R)-2-(7-amino-5-nitroimidazo[4,5-b]pyridin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 306275-35-4
• 化学式: C₁₁H₁₃N₅O₆
• 分子量: 311.254
• InChiKey: PUPNADBYINJVTB-MGUDNFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 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：
  173
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-nitro-1-deazaadenosine 在 吡啶 作用下， 以66%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：

  Synthesis and Stability Studies of 2′,3′,5′-tri-O-Acetyl-2-Amino(-N⁶-Cyclopentyl)-1-Deazaadenosines

  摘要：

  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.

  DOI：

  10.1080/15257770701542231
• 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 甲醇 、 potassium cyanide 、 sodium azide 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 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

文献信息

• 2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes
  作者：Martin J. Wanner、Jacobien K. Von Frijtag Drabbe Künzel、Ad P. IJzerman、Gerrit-Jan Koomen

  DOI：10.1016/s0960-894x(00)00415-7

  日期：2000.9

  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.
• 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.