1-O-propynyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose | 66981-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-propynyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
• 英文别名: 2-propynyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside；propargyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside；Propargyl-2,3,5-tri-O-benzoyl-β-D-ribofuranoside；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-prop-2-ynoxyoxolan-2-yl]methyl benzoate
• CAS: 66981-55-3
• 化学式: C₂₉H₂₄O₈
• 分子量: 500.505
• InChiKey: WRUACBCYGASYKR-DOUCHOMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-propynyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 在 mercury(II) trifluoroacetate 、 四氯化锡 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 22.0h， 生成 2',3',5'-tri-O-benzoyluridine
  参考文献：
  名称：

  [（β-D-呋喃呋喃糖基氧基）甲基]核苷的合成。

  摘要：

  乙酰氧基甲氧基核呋喃糖核苷4与核酸碱基5a-f的偶联反应分别优先于预期形成的天然核苷2'，3'，分别合成新颖的（核呋喃糖基氧基）甲基尿嘧啶，胸腺嘧啶，胞嘧啶，腺嘌呤，鸟嘌呤衍生物6a-g，描述了5'-三-O-苯甲酰尿苷，甲基尿苷，胞苷，腺苷和鸟苷7a-g。描述了由路易斯酸TMSOTf和SnCl4催化的这些反应的详细研究。TMSOTf显示出形成呋喃核糖基氧基甲基衍生物6a-g而不是7a-g的选择性。HSAB原理解释了形成6a-g的原因。

  DOI：

  10.1081/ncn-120030722
• 作为产物：
  描述：

  2-丙炔-1-醇 、 1-乙酰基-三-苄氧基-罗伯糖 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以68%的产率得到1-O-propynyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
  参考文献：
  名称：

  [（β-D-呋喃呋喃糖基氧基）甲基]核苷的合成。

  摘要：

  乙酰氧基甲氧基核呋喃糖核苷4与核酸碱基5a-f的偶联反应分别优先于预期形成的天然核苷2'，3'，分别合成新颖的（核呋喃糖基氧基）甲基尿嘧啶，胸腺嘧啶，胞嘧啶，腺嘌呤，鸟嘌呤衍生物6a-g，描述了5'-三-O-苯甲酰尿苷，甲基尿苷，胞苷，腺苷和鸟苷7a-g。描述了由路易斯酸TMSOTf和SnCl4催化的这些反应的详细研究。TMSOTf显示出形成呋喃核糖基氧基甲基衍生物6a-g而不是7a-g的选择性。HSAB原理解释了形成6a-g的原因。

  DOI：

  10.1081/ncn-120030722

文献信息

• The Fight against the Influenza A Virus H1N1: Synthesis, Molecular Modeling, and Biological Evaluation of Benzofurazan Derivatives as Viral RNA Polymerase Inhibitors
  作者：Mafalda Pagano、Daniele Castagnolo、Martina Bernardini、Anna Lucia Fallacara、Ilaria Laurenzana、Davide Deodato、Ulrich Kessler、Beatrice Pilger、Lilli Stergiou、Stephan Strunze、Cristina Tintori、Maurizio Botta

  DOI：10.1002/cmdc.201300378

  日期：2014.1

  The influenza RNA polymerase complex, which consists of the three subunits PA, PB1, and PB2, is a promising target for the development of new antiviral drugs. A large library of benzofurazan compounds was synthesized and assayed against influenza virus A/WSN/33 (H1N1). Most of the new derivatives were found to act by inhibiting the viral RNA polymerase complex through disruption of the complex formed

  由PA，PB1和PB2三个亚基组成的流感RNA聚合酶复合物是开发新抗病毒药物的有希望的目标。合成了庞大的苯并呋喃化合物文库，并针对流感病毒A / WSN / 33（H1N1）进行了分析。发现大多数新衍生物通过破坏亚基PA和PB1之间形成的复合物来抑制病毒RNA聚合酶复合物而发挥作用。还进行了对接研究，以阐明PA中PB1结合位点内苯并呋喃类的结合方式，并鉴定参与其作用机理的氨基酸。预测的结合姿势与生物学数据完全一致，为合理开发更有效的PA–PB1抑制剂奠定了基础。
• 1,2,3-Triazole-containing flex-nucleoside analogs and sulfonamido-ribofuranoside conjugates: design, synthesis, and antiproliferative potential
  作者：Dijana Pavlović Saftić、Željka Ban、Katarina Mišković Špoljarić、Ljubica Glavaš-Obrovac、Biserka Žinić

  DOI：10.1039/d3nj03724j

  日期：——

  alkyl halides and NaN3, or 5-azido sugars were used. CuAAC click reactions were performed under classical conditions, and C5-triazolyl-uracil/uridine derivatives were prepared in good yields. Two synthetic routes were used to prepare 1,4-disubstituted 1,2,3-triazolyl-sulfonamido-ribofuranoside conjugates. The first 1,2,3-triazolyl-ribofuranoside conjugate, where a 1,2,3-triazole ring links two ribose

  描述了新的C 5-[1,2,3]三唑基-尿嘧啶/尿苷柔性聚合物和 1,2,3-三唑基-磺酰胺基-呋喃核苷缀合物的设计和合成，可用作制备更复杂分子的通用构建模块。为了制备C 5-三唑基-嘧啶衍生物，使用Sonogashira偶联合成起始5-乙炔基-尿嘧啶/尿苷衍生物，并使用烷基卤原位生成叠氮化物和NaN 3或5-叠氮糖。CuAAC 点击反应在经典条件下进行，C以良好的产率制备了 5-三唑基-尿嘧啶/尿苷衍生物。使用两种合成路线来制备1,4-二取代的1,2,3-三唑基-磺酰胺基-呋喃核苷缀合物。第一个 1,2,3-三唑基-呋喃核苷缀合物，其中 1,2,3-三唑环连接两个核糖，通过点击反应合成，然后使用市售磺酰胺转化为磺酰胺基-呋喃核苷缀合物。然而，磺酰胺糖苷化反应以低产率得到所需产物。在第二条路线中，合成了5-叠氮基-核糖基-磺酰胺，然后将其在微波反应器中与末端糖炔进行点击反应，得到所需的1,4-二取代的1
• Carbonic Anhydrase Inhibitors:  Inhibition of Isozymes I, II, and IX with Triazole-Linked <i>O</i>-Glycosides of Benzene Sulfonamides
  作者：Brendan L. Wilkinson、Laurent F. Bornaghi、Todd A. Houston、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm061320h

  日期：2007.4.1

  We report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low-nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 and 9.7-107 nM, respectively, was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (K-i = 9.7 nM); this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.
• Highly Efficient <i>O</i>-Glycosylations with <i>p</i>-Tolyl Thioribosides and <i>p</i>-TolSOTf
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/jo801408x

  日期：2008.12.19

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.