2-nitroadenosine pentaacetate | 266360-70-7

• 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: 2-nitroadenosine pentaacetate
• 英文别名: 2-nitro-adenosine pentaacetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-(diacetylamino)-2-nitropurin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 266360-70-7
• 化学式: C₂₀H₂₂N₆O₁₁
• 分子量: 522.428
• InChiKey: XNLWOLKCCPOLFA-NVQRDWNXSA-N

物化性质

• 沸点：
  797.1±70.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  215
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-nitroadenosine pentaacetate 在 镍 potassium cyanide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 2-氨基腺嘌呤核苷
  参考文献：
  名称：

  Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

  摘要：

  Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02271-6
• 作为产物：
  描述：

  2',3',5'-三乙酰腺苷 在 4-二甲氨基吡啶 、 四丁基硝酸铵 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 2-nitroadenosine pentaacetate
  参考文献：
  名称：

  Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

  摘要：

  Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02271-6

文献信息

• [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES<br/>[FR] SYNTHESE AMELIOREE D'ADENOSINES SUBSTITUEES EN 2
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005056571A1

  公开（公告）日：2005-06-23

  Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R = C1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-,cyano, nitro, C1-6 alkyl, or C1-6 alkoxy). The methods provide improved yield and purity of product.

  使用2-硝基戊二酰基腺苷或2-硝基戊醋酰基腺苷作为中间体，描述了合成式(I)的2-取代腺苷的方法：式(I)中，R = C1-6烷氧基（直链或支链）、苯氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、苄氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、或苯甲酰基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）。该方法提供了改善产物产量和纯度的效果。
• 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.