3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl azide | 223498-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl azide
• 英文别名: 1,2-dideoxy-1-azido-3,5-di-O-acetyl-β-D-ribofuranose；[(2R,3S,5R)-3-acetyloxy-5-azidooxolan-2-yl]methyl acetate
• CAS: 223498-34-8
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: XLRKLLFICSSZGE-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl azide 在 甲醇 、 potassium carbonate 作用下， 反应 12.0h， 以92%的产率得到2-deoxy-β-D-erythro-pentofuranosyl azide
  参考文献：
  名称：

  Synthesis and Calcium Mobilization Activity of cADPR Analogues Which Integrate Nucleobase, Northern and Southern Ribose Modifications

  摘要：

  我们合成了新型的 cADPR 模拟物，它整合了核碱基、北核糖和南核糖修饰。合成的关键步骤是 Cu（I）催化的 Hüisgen [3+2] 环加成和微波辅助的分子内焦磷酸化。初步的生物学研究表明，这些 cADPR 模拟物是钙信号通路的膜渗透激动剂。在南部核糖的 2'- 位上引入氯或氟会导致活性降低。南方核糖 3'-OH 上疏水基团的存在并不会明显改变其激动活性。

  DOI：

  10.3390/molecules17044343
• 作为产物：
  描述：

  2-脱氧-beta-D-赤式-呋喃戊糖 在 iron(III) chloride 、 叠氮基三甲基硅烷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.58h， 生成 3,5-di-O-acetyl-2-deoxy-β-D-ribofuranosyl azide
  参考文献：
  名称：

  Ultrasound-assisted one-pot synthesis of anti-CML nucleosides featuring 1,2,3-triazole nucleobase under iron-copper catalysis

  摘要：

  A simple and efficient synthesis of modified 1,2,3-triazole nucleosides was developed. The strategy involved sequential one-pot acetylation-azidation-cycloaddition procedure and was found to be highly effective under a cooperative effect of ultrasound activation and iron/copper catalysis. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions. This one-pot procedure provides several advantages such as operational simplicity, high yield, safety and environment friendly protocol. The resulting substituted nucleosides were evaluated for their anticancer activity against K562 chronic myelogenous leukemia (CML) cell line Crown Copyright (C) 2012 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.04.007

文献信息

• Efficient and selective azidation of per-O-acetylated sugars using ultrasound activation: application to the one-pot synthesis of 1,2,3-triazole glycosides
  作者：Hamid Marzag、Soukaina Alaoui、Hella Amdouni、Anthony R. Martin、Khalid Bougrin、Rachid Benhida

  DOI：10.1039/c5nj00624d

  日期：——

  A new protocol was developed for the selective transformation of acetyl-sugars to triazolyl nucleosides using in situ generated SO₂(N₃)₂, iron/copper cocatalysis and ultrasound activation.

  开发了一种新的协议，用于将乙酰糖选择性转化为三唑基核苷，使用现场生成的SO₂(N₃)₂，铁/铜共催化和超声波激活。
• In Vitro and in Vivo Evaluation of Fully Substituted (5-(3-Ethoxy-3-oxopropynyl)-4-(ethoxycarbonyl)-1,2,3-triazolyl-glycosides as Original Nucleoside Analogues to Circumvent Resistance in Myeloid Malignancies
  作者：Hella Amdouni、Guillaume Robert、Mohsine Driowya、Nathan Furstoss、Camille Métier、Alix Dubois、Maeva Dufies、Marwa Zerhouni、François Orange、Sandra Lacas-Gervais、Khalid Bougrin、Anthony R. Martin、Patrick Auberger、Rachid Benhida

  DOI：10.1021/acs.jmedchem.6b01803

  日期：2017.2.23

  yy A series of nucleoside analogues bearing a 1,4,5-trisubstituted-1,2,3-triazole aglycone was synthesized using a straightforward click/electrophilic addition or click/oxidative coupling tandem procedures. SAR analysis, using cell culture assays, led to the discovery of a series of compounds belonging to the 5-alkynyl-1,2,3-triazole family that exhibits potent antileukemic effects on several hematologic malignancies including chronic myeloid leukemia (CML) and myelodysplastic syndromes (MDS) either sensitive or resistant to their respective therapy. Compound 4a also proved efficient in-vivo on mice xenografted with SKM1-R MDS cell line. Additionally, some insights in its mode of action revealed that this compound induced cell death by caspase and autophagy induction.
• Stereoselective Construction of 1β-Azide- and 1β-Cyano-2-deoxyribose Derivatives
  作者：Hiromichi Fujioka、Kazuhisa Okamoto、Yutaka Minamitsuji、Yoshifumi Ueyama、Nao Matsumoto、Kenichi Murai

  DOI：10.3987/com-14-s(k)86

  日期：——

  A new method has been developed for the beta-selective introduction of azido and cyano groups at the anomeric position of 2-deoxyribose derivatives. This method proceeds via the formation of a collidinium salt intermediate and allows for the stereoselective construction of 1 beta-azido- and 1 beta-cyano-2-deoxy-D-ribose derivatives. 2-Deoxy-D-ribose compounds bearing an acetoxy or tert-butoxycarbonyloxy group at their anomeric position performed well as starting materials for the formation of the corresponding 1 beta-azide and 1 beta-cyanide derivatives, respectively. H-1 NMR studies of the salt intermediates revealed that the nucleophilic substitution reaction of the salt intermediates proceeded in a S(N)2-fashion.
• Optimization of the Natural Product Calothrixin A to Discover Novel Dual Topoisomerase I and II Inhibitors with Improved Anticancer Activity
  作者：Xiaohong Yang、Zhi-Peng Wang、Sichuan Xiang、Daoqiang Wang、Yi Zhao、Dong Luo、Yanfei Qiu、Chao Huang、Jian Guo、Yuanwei Dai、Shao-Lin Zhang、Yun He

  DOI：10.1021/acs.jmedchem.2c00615

  日期：2022.6.9