6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine | 266360-74-1

• 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: 6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine
• 英文别名: O^2',O^3',O^5'-triacetyl-2-nitroadenosine；2-nitroadenosine triacetate；6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-beta-d-ribofuranosyl)purine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-amino-2-nitropurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 266360-74-1
• 化学式: C₁₆H₁₈N₆O₉
• 分子量: 438.354
• InChiKey: SZWCZDJJTBRIRX-SDBHATRESA-N

物化性质

• 沸点：
  701.1±70.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  204
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 以68%的产率得到2-nitroadenosine
  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-O-乙酰基-6-氯嘌呤-9-β-D-呋喃核糖苷 在 sodium azide 、 四丁基硝酸铵 、 溶剂黄146 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine
  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

• FORMATION OF 2?-DEOXY-2-NITROADENOSINES BY REACTION OF 2?-DEOXYADENOSINES WITH COPPER(II) NITRATE/ACETIC ANHYDRIDE
  作者：Toyo Kaiya、Haruko Tanaka、Kohfuku Kohda

  DOI：10.1081/ncn-120014815

  日期：——

  ABSTRACT Nitration of 9-substituted [ethyl, (Ac)2-2′-deoxyribosyl, (Ac)3-ribosyl] N 6-acetyladenine derivatives with Cu(NO3)2·3H2O/Ac2O was examined. Nitration proceeded at the 2-position, although the yield was low. Removal of the acetyl groups gave 2′-deoxy-2-nitroadenosine derivatives.

  摘要 研究了 9-取代的 [乙基，(Ac)2-2'-脱氧核糖基，(Ac)3-核糖基]N 6-乙酰腺嘌呤衍生物与 Cu(NO3)2·3H2O/Ac2O 的硝化反应。尽管产率低，但硝化作用在 2 位进行。去除乙酰基得到 2'-脱氧-2-硝基腺苷衍生物。
• Photochemistry of 6-amino-2-azido, 2-amino-6-azido and 2,6-diazido analogues of purine ribonucleosides in aqueous solutions
  作者：Krzysztof Komodziński、Jolanta Lepczyńska、Zofia Gdaniec、Libero Bartolotti、Bernard Delley、Stefan Franzen、Bohdan Skalski

  DOI：10.1039/c3pp50385b

  日期：2014.3

  2-amino-6-azidopurine and 2,6-diazidopurine ribonucleosides has been investigated in aqueous solutions under aerobic and anaerobic conditions. Near UV irradiation of 6-amino-2-azido-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)purine and 2-amino-6-azido-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)purine in the presence of oxygen leads to efficient formation of 6-amino-2-nitro-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)purine

  在有氧和无氧条件下，研究了6-氨基-2-叠氮嘌呤，2-氨基-6-叠氮嘌呤和2,6-二叠氮嘌呤核糖核苷的光化学性质。6-氨基-2-叠氮基-9-（2'，3'，5'-三-O-乙酰基-β - D-核呋喃糖基）嘌呤和2-氨基-6-叠氮基-9-（2的近紫外辐射'，3'，5'-三-O-乙酰基-β - D-呋喃呋喃糖基）嘌呤在氧气存在下导致有效形成6-氨基-2-硝基-9-（2'，3'，5' -三-O-乙酰基-β - D-呋喃核糖基）嘌呤和2-氨基-6-硝基-9-（2'，3'，5'-三-O-乙酰基-β - D-核呋喃糖基）嘌呤。在厌氧条件下，两个叠氮嘌呤核糖核苷均优先经历光还原为2,6-二氨基-9-（2'，3'，5'-tri- O-乙酰基-β - D-核呋喃糖基）嘌呤。通过UV，NMR和HR ESI-TOF MS光谱数据确认形成的光产物的结构。在这项研究中观察到的氨基叠氮嘌呤的光产物与以前观察到的6-叠氮嘌
• 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.
• Tetrahedron Letters. 2000, 41, 1291-1295
  作者：

  DOI：——

  日期：——