1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-ribofuranose | 186301-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-ribofuranose
• 英文别名: [(2R,3R,4R)-4,5-diacetyloxy-2-(azidomethyl)oxolan-3-yl] acetate
• CAS: 186301-50-8
• 化学式: C₁₁H₁₅N₃O₇
• 分子量: 301.256
• InChiKey: ZAFHUFUBCYMYLP-QHPFDFDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-ribofuranose 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 29.25h， 生成 N4-benzoyl-1-[2-O-(2,3-di-O-acetyl-5-azido-5-deoxy-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine
  参考文献：
  名称：

  Oligonucleotides Containing Disaccharide Nucleosides

  摘要：

  Disaccharide nucleosides with 2'-O-(D-arabinofuranosyl), 2'-O-(L-arabinofuranosyl), 2'-O-(D-ribopyranosyl), 2'-O-(D-erythrofuranosyl), and 2'-O-(5-azido-5-deoxy-D-ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a DeltaT(m) of +0.5 to -1.4 degrees for DNA/RNA and a DeltaT(m) of - 0.8 to -4.7 degrees for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH2- C(5") group has a beneficial effect on duplex stability.

  DOI：

  10.1002/1522-2675(20010815)84:8<2387::aid-hlca2387>3.0.co;2-f
• 作为产物：
  描述：

  ((3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate 在 sodium azide 、 硫酸 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-ribofuranose
  参考文献：
  名称：

  基于核苷的抗原生动物化合物的合成和活性。

  摘要：

  寄生虫的原生动物利用挽救途径合成嘌呤并产生必需的活性核苷酸，而哺乳动物则能够从头进行生物合成。这种差异为设计潜在的新抗原生动物化合物提供了机会。基于以下假设制备了一系列47个腺苷类似物，它们在2、6和5'位置有修饰，这是基于这样的假设，即此类化合物可作为原生动物核苷挽救酶的底物，而在哺乳动物细胞中仍然是难降解的。核苷经设计可在被寄生虫裂解为相应的嘌呤碱基后产生有毒代谢物。制备了具有相似目的的三种7-脱氮鸟苷衍生物。所有这些化合物均经过体外抗T. brucei（非洲昏睡病），T。cruzi（恰加斯氏病），L。donovani（利什曼病）和恶性疟原虫（疟疾）。为了确定抗原生动物核苷的治疗选择性指数（SI），还测定了它们对大鼠成肌细胞系的细胞毒性。一种腺苷衍生物被证明对恶性疟原虫高度有效（IC50 = 110nM，SI = 1010），而改良的鸟苷则对杜氏疟原虫（IC50 = 60nM，SI =

  DOI：

  10.1016/j.bmc.2017.02.016

文献信息

• Design, synthesis and biological evaluation of 5′-C-piperidinyl-5′-O-aminoribosyluridines as potential antibacterial agents
  作者：Takeshi Nakaya、Akira Matsuda、Satoshi Ichikawa

  DOI：10.1039/c5ob01037c

  日期：——

  Caprazamycin analogues, which were designed and synthesized via an aza-Prins–Ritter reaction, exhibit a good MraY and antibacterial activity without cytotoxicity against human cells.

  卡普拉霉素类似物是通过一种氮杂Prins-Ritter反应设计和合成的，表现出良好的MraY和抗菌活性，且对人类细胞没有细胞毒性。
• Apralogs: Apramycin 5-<i>O</i>-Glycosides and Ethers with Improved Antibacterial Activity and Ribosomal Selectivity and Reduced Susceptibility to the Aminoacyltransferase (3)-IV Resistance Determinant
  作者：Jonathan C. K. Quirke、Parasuraman Rajasekaran、Vikram A. Sarpe、Amr Sonousi、Ivan Osinnii、Marina Gysin、Klara Haldimann、Qiao-Jun Fang、Dimitri Shcherbakov、Sven N. Hobbie、Su-Hua Sha、Jochen Schacht、Andrea Vasella、Erik C. Böttger、David Crich

  DOI：10.1021/jacs.9b11601

  日期：2020.1.8

  Apramycin is a structurally unique member of the 2-deoxystreptamine class of aminoglycoside antibiotics characterized by a mono-substituted 2-deoxystreptamine ring that carries an unusual bicyclic eight-carbon dialdose moiety. Because of its unusual structure apramycin is not susceptible to the most prevalent mechanisms of aminoglycoside resistance including the aminoglycoside-modifying enzymes and

  安普霉素是 2-脱氧链霉胺类氨基糖苷类抗生素的一种结构独特的成员，其特征在于带有一个不寻常的双环八碳二糖部分的单取代 2-脱氧链霉胺环。由于其不寻常的结构，安普霉素不易受到最普遍的氨基糖苷类耐药机制的影响，包括氨基糖苷类修饰酶和核糖体甲基转移酶，它们的广泛存在严重损害了当前临床实践中的所有氨基糖苷类。这些特性与动物模型中最低的耳毒性相结合，使安普霉素成为开发下一代氨基糖苷类抗生素治疗多重耐药细菌感染（尤其是 ESKAPE 病原体）的极好起点。考虑到这一点，我们描述了设计，合成和评估三个系列的安普霉素衍生物，均在 5 位官能化，目的是在不牺牲细菌和真核核糖体之间选择性的情况下提高抗菌效力，并克服罕见的氨基糖苷乙酰转移酶 (3)-IV 类氨基糖苷类修饰酶，它构成了对安普霉素的抗菌素耐药性的唯一记录机制。我们表明几种 apramycin-5-O-β-D-呋喃核糖苷、5-O-β-D-eryrthofuranosides
• [EN] NUCLEOSIDE-BASED ANTI-BACTERIAL AND ANTI-PROTOZOAN DRUGS<br/>[FR] MÉDICAMENTS ANTIBACTÉRIENS ET ANTI-PROTOZOAIRES À BASE DE NUCLÉOSIDES
  申请人：UTI LIMITED PARTNERSHIP

  公开号：WO2016168911A1

  公开（公告）日：2016-10-27

  The present invention is directed to purine nucleoside analogs of the general formula (I) or salts and pharmaceutical compositions comprising such compounds and salts, which are useful as anti-protozoan agents. The invention is also directed to methods for treating a protozoan infection in a mammal and use of the compounds for inhibiting the growth of protozoa.

  本发明涉及通式（I）的嘌呤核苷类似物或其盐以及包含这些化合物和盐的药物组合物，这些化合物和盐可用作抗原生虫剂。该发明还涉及用于治疗哺乳动物原生动物感染的方法以及利用这些化合物抑制原生动物生长的用途。
• Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors
  作者：Xiu-Hua Xu、Amy E. Trunkfield、Timothy D. H. Bugg、Feng-Ling Qing

  DOI：10.1039/b713068f

  日期：——

  Two gem-difluoromethylenated nucleoside moieties of liposidomycins, 3 and 4, were designed and synthesized. Compound 3 was assembled from lactol5 and gem-difluoromethylenated nucleoside6. In the synthesis of target molecule 4, the coupling of the trichloroacetimidate derivative of gem-difluoromethylenated furanose7 with nucleoside8 in the presence of TMSOTf gave the unexpected compound 16 when CH3CN was used as solvent. This results from acetonitrile acting as a nucleophile and participating in the glycosylation reaction. This unusual process may be correlated with the presence of the electron-withdrawing gem-difluoro substituents at the C-2 position of furanose. Compound 3 demonstrated 29% inhibition of MraY at 11.4 mM.

  两种含有gem-二氟亚甲基的核苷部分的脂肪霉素，3和4，进行了设计和合成。化合物3是由醇盐5和gem-二氟亚甲基核苷6组装而成。在目标分子4的合成中，gem-二氟亚甲基呋喃糖7的三氯乙酰亚胺衍生物与核苷8的耦合在TMSOTf的存在下，使用CH3CN作为溶剂时意外产生了化合物16。这是因为乙腈作为亲核试剂参与了糖苷化反应。这一异常过程可能与呋喃糖C-2位置上存在的吸电子gem-二氟取代基有关。化合物3在11.4 mM浓度下对MraY表现出29%的抑制作用。
• Glucose isomerase catalysed isomerisation reactions of (2R,3R)-configured aldofuranoses into the corresponding open-chain 2-ketoses
  作者：Michael Ebner、Arnold E. Stütz

  DOI：10.1016/s0008-6215(97)00206-1

  日期：1997.12

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R)-configured aldofuranoses such as D-erythrose, as well as homologous C-5-modified D-ribose derivatives, as substrates. In the case of D-erythrose, quantitative conversion into D-glycero-tetrulose took place. D-Ribofuranoses were converted into the corresponding open-chain 2-ketoses in isolated yields of 65%. Surprisingly, L-erythrose also turned out to be a substrate of this enzyme. (C) 1998 Elsevier Science Ltd.