3-O-benzoyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose | 1308305-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-benzoyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-(azidomethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 1308305-52-3
• 化学式: C₁₅H₁₇N₃O₅
• 分子量: 319.317
• InChiKey: SNCPSDXXBCDBLD-GFQSEFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-乙炔基吡啶 、 3-O-benzoyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以93%的产率得到3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-5-(4-(2-pyridyl)-1H-1,2,3-triazole-1-yl)-α-D-xylofuranose
  参考文献：
  名称：

  Palladium(II) carbohydrate complexes of alkyl, aryl and ferrocenyl esters and their cytotoxic activities

  摘要：

  This article describes the synthesis and cytotoxic activities of palladium(II) carbohydrate complexes of methyl, phenyl and ferrocenyl ester derivatives. The 3-O-ferrocenoyl-1,2-O-isopropylidene-alpha-D-xylofuranose triazole (2c) was prepared by the Huisgen 1,3-dipolar cycloaddition reaction of 2-ethynyl pyridine and 5-azido-5-deoxy-3-O-ferrocenoyl-1,2-O-isopropylidene-alpha-D-xylofuranose (1c). The reaction of this conjugate with [Pd(COD)Cl-2] in anhydrous dichloromethane formed the corresponding palladium(II) complex (3c). The ligands and the complexes were characterised by H-1 NMR, ESI mass, IR and elemental analysis. The UV-Vis and CV studies were also performed for the metal complexes. The electronic absorption spectra of complexes 3a-c shows the presence of both triazole and ferrocene absorption bands. Electrochemical studies of complexes 3a-c show the presence of a reduction peak at around -0.84 V thereby indicating the conversion of Pd(II) to Pd(0). The in vitro cytotoxic activity was studied against a panel of four different cancer cell lines. It was observed that these compounds exhibited significant cytotoxicity specifically on A549 cancer cell line. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.03.018
• 作为产物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以91%的产率得到3-O-benzoyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  (4-Ferrocenylphenyl)propargyl ether derived carbohydrate triazoles: influence of a hydrophobic linker on the electrochemical and cytotoxic properties

  摘要：

  在本文中，我们详细研究了疏水性连接子对一系列费罗烯–碳水化合物共轭物性质的影响。通过炔基溴化物与4-费罗烯基苯酚的反应制备了炔烃（4-费罗烯基苯基）丙炔醚。通过单晶X射线衍射研究确定了炔烃的结构。为了在电化学和细胞毒性研究中进行比较，合成了一种苄基三唑（3a）。在此，我们报告通过Huisgen 1,3-偶极环加成反应使用一系列碳水化合物叠氮化物与（4-费罗烯基苯基）丙炔醚合成和表征了一系列碳水化合物三唑共轭物（3b–h）。对炔烃和三唑化合物进行了紫外可见光谱和电化学研究。由循环伏安研究生成的数据用于计算费罗烯–碳水化合物共轭物在DMSO和DMSO–缓冲液中的扩散系数（Df）。在缓冲液中，碳水化合物三唑共轭物（3b–h）的扩散系数值稍高，这可能是由于连接子的疏水特性和费罗烯核心附近缺乏氢键取代基。此外，来源于核糖呋喃糖的三唑共轭物（3f）对激素依赖性乳腺癌细胞系（MCF-7）显示出显著的细胞毒性，IC50值低于10 μM。

  DOI：

  10.1039/c3nj01022h

文献信息

• 2,4‐Thiazolidinedione as a Bioactive Linker for Ferrocenyl Sugar–Triazole Conjugates: Synthesis, Characterization and Biological Properties
  作者：Dilip N. Shinde、Rajiv Trivedi、Narra Vamsi Krishna、Giribabu Lingamallu、Balasubramanian Sridhar、Parag S. Khursade、Prakasham Reddy Shetty

  DOI：10.1002/ejic.201800006

  日期：2018.4.17

  A new series of ferrocenyl sugar–triazole conjugates, derived from d‐xylose, d‐ribose and d‐galactose, linked by a 2,4‐thiazolidinedione moiety, has been prepared. Facile 1,3‐dipolar‐Huisgen coupling reactions of the respective sugar azides with the ferrocenyl 2,4‐thiazolidinedione alkyne units give the corresponding conjugates. These conjugates have been characterized by various spectroscopic techniques

  制备了一系列新的二茂铁基糖-三唑共轭物，它们由d-木糖，d-核糖和d-半乳糖与2,4-噻唑烷二酮部分连接而成。各个糖叠氮化物与二茂铁基2,4-噻唑烷二酮炔单元的简便1,3-偶极-惠斯根偶联反应给出了相应的缀合物。这些缀合物已通过各种光谱技术进行了表征，包括UV / Vis光谱。电化学分析显示出单电子可逆氧化行为，除了5c和5f表现出准可逆行为。两种化合物（2和3的单晶X射线衍射研究）以确定它们的结构。2,4-噻唑烷二酮连接的二茂铁基糖-三唑共轭物表现出中等至良好的抗菌和抗糖尿病活性。
• 1,3-Dipolar cycloaddition of sugar azides with benzyne: a novel synthesis of 1,2,3-benzotriazolyl glycoconjugates
  作者：Basi V. Subba Reddy、Karanam Praneeth、Jhillu S. Yadav

  DOI：10.1016/j.carres.2010.12.015

  日期：2011.6

  Glycosyl azides undergo smooth 1,3-dipolar cycloaddition with benzyne generated in situ from 2-(trimethylsilyl)phenyltrifluoromethanesulfonate and cesium fluoride under mild conditions to furnish 1,2,3-benzotriazole-linked glycoconjugates in excellent yields and with high stereoselectivity. This method provides a novel class of benzotriazole linked glycoconjugates in a single-step reaction. This is

  糖基叠氮化物与2-（三甲基甲硅烷基）苯基三氟甲磺酸盐和氟化铯在温和的条件下原位生成的苯炔进行平滑的1,3-偶极环加成反应，以优异的产率和高的立体选择性提供1,2,3-苯并三唑连接的糖缀合物。该方法在一步反应中提供了一类新型的苯并三唑连接的糖缀合物。这是苯并与糖基叠氮化物的氟化物引发的1,3-偶极环加成反应的第一个例子。
• Palladium(II) carbohydrate complexes of alkyl, aryl and ferrocenyl esters and their cytotoxic activities
  作者：Sadanala Bhavya Deepthi、Rajiv Trivedi、Lingamallu Giribabu、Pombala Sujitha、C. Ganesh Kumar

  DOI：10.1016/j.ica.2014.03.018

  日期：2014.5

  This article describes the synthesis and cytotoxic activities of palladium(II) carbohydrate complexes of methyl, phenyl and ferrocenyl ester derivatives. The 3-O-ferrocenoyl-1,2-O-isopropylidene-alpha-D-xylofuranose triazole (2c) was prepared by the Huisgen 1,3-dipolar cycloaddition reaction of 2-ethynyl pyridine and 5-azido-5-deoxy-3-O-ferrocenoyl-1,2-O-isopropylidene-alpha-D-xylofuranose (1c). The reaction of this conjugate with [Pd(COD)Cl-2] in anhydrous dichloromethane formed the corresponding palladium(II) complex (3c). The ligands and the complexes were characterised by H-1 NMR, ESI mass, IR and elemental analysis. The UV-Vis and CV studies were also performed for the metal complexes. The electronic absorption spectra of complexes 3a-c shows the presence of both triazole and ferrocene absorption bands. Electrochemical studies of complexes 3a-c show the presence of a reduction peak at around -0.84 V thereby indicating the conversion of Pd(II) to Pd(0). The in vitro cytotoxic activity was studied against a panel of four different cancer cell lines. It was observed that these compounds exhibited significant cytotoxicity specifically on A549 cancer cell line. (C) 2014 Elsevier B.V. All rights reserved.
• (4-Ferrocenylphenyl)propargyl ether derived carbohydrate triazoles: influence of a hydrophobic linker on the electrochemical and cytotoxic properties
  作者：Sadanala Bhavya Deepthi、Rajiv Trivedi、Lingamallu Giribabu、Pombala Sujitha、C. Ganesh Kumar、B. Sridhar

  DOI：10.1039/c3nj01022h

  日期：——

  In this article we describe a detailed study of the influence of a hydrophobic linker on the properties of a series of ferrocene–carbohydrate conjugates. The alkyne, (4-ferrocenylphenyl)propargyl ether, was prepared from the reaction of propargyl bromide and 4-ferrocenylphenol. The structure of the alkyne was determined using a single crystal X-ray diffraction study. A benzyl triazole (3a) was synthesised for comparison purposes in the electrochemical and cytotoxic study. Herein, we report the synthesis and characterization of a series of carbohydrate triazole conjugates (3b–h) by using the Huisgen 1,3-dipolar cycloaddition reaction of a series of carbohydrate azides and (4-ferrocenylphenyl)propargyl ether. UV-visible spectroscopy and electrochemical studies were performed on the alkyne and triazole compounds. The data generated from the cyclic voltammetric studies was used to calculate the diffusion coefficients (Df) of the ferrocene–carbohydrate conjugates in DMSO and DMSO–buffer solutions. Slightly higher diffusion coefficient values were obtained for the carbohydrate triazole conjugates (3b–h) in the buffer solution, perhaps due to the hydrophobic nature of the linker and the absence of a hydrogen-bonding substituent adjacent to the ferrocene core. Furthermore, the triazole conjugate (3f) derived from ribofuranose exhibited significant cytotoxicity against a hormone dependent breast cancer cell line (MCF-7) with an IC50 value lower than 10 μM.

  在本文中，我们详细研究了疏水性连接子对一系列费罗烯–碳水化合物共轭物性质的影响。通过炔基溴化物与4-费罗烯基苯酚的反应制备了炔烃（4-费罗烯基苯基）丙炔醚。通过单晶X射线衍射研究确定了炔烃的结构。为了在电化学和细胞毒性研究中进行比较，合成了一种苄基三唑（3a）。在此，我们报告通过Huisgen 1,3-偶极环加成反应使用一系列碳水化合物叠氮化物与（4-费罗烯基苯基）丙炔醚合成和表征了一系列碳水化合物三唑共轭物（3b–h）。对炔烃和三唑化合物进行了紫外可见光谱和电化学研究。由循环伏安研究生成的数据用于计算费罗烯–碳水化合物共轭物在DMSO和DMSO–缓冲液中的扩散系数（Df）。在缓冲液中，碳水化合物三唑共轭物（3b–h）的扩散系数值稍高，这可能是由于连接子的疏水特性和费罗烯核心附近缺乏氢键取代基。此外，来源于核糖呋喃糖的三唑共轭物（3f）对激素依赖性乳腺癌细胞系（MCF-7）显示出显著的细胞毒性，IC50值低于10 μM。