3-O-Acetyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose | 328314-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-Acetyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
• CAS: 328314-03-0
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: DMDMMRCMLYDFRD-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  102.75
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-O-Acetyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 焦磷酸硫胺素 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 65.0h， 生成 1,2,3-tri-O-acetyl-5-deoxy-5-isothiocyanato-D-xylofuranose
  参考文献：
  名称：

  Calystegine B2类似物作为糖苷酶抑制剂的合成和评估。

  摘要：

  提出了一种实用的多羟基化的6-氧杂-正-烷烷类化合物，由5-脱氧-5-硫脲基和5-脲基-L-呋喃丹糖前体结合了calystegine B（2）的基本结构特征。该方法依赖于假酰胺型氮原子（硫脲，尿素和氨基甲酸酯）对单糖的掩蔽醛基进行亲核加成的能力。产生的半胱氨酸功能性可以进一步进行原位分子内糖苷化以产生双环氨基缩醛化合物，整个过程受到异头作用的促进。已经制备了一系列在氮原子上带有不同取代基的衍生物，并与木糖苷嘧啶型哌啶类似物相比，针对几种糖苷酶进行了筛选。有趣的是 强烈和高度特异性抑制牛肝β-葡糖苷酶的6-氧杂天冬氨酸B（2）类似物并入芳香假糖苷基团。基于这些数据，针对该糖模拟物家族提出了一种1-氮杂糖抑制模式。

  DOI：

  10.1021/jo015639f
• 作为产物：
  描述：

  乙酸酐 、 1,2-O-异亚丙基-alpha-D-呋喃木糖 在 迭氮酸 、 三苯基膦 、 偶氮二甲酸二乙酯 、 吡啶 作用下， 以 吡啶 、 苯 为溶剂， 反应 0.25h， 以59%的产率得到3-O-Acetyl-5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Mitsunobu Transformations of 1,2-O-Isopropylidene-α-D-pentofuranoses Mediated by Zinc Salts

  摘要：

  一锅法的选择性杂功能化反应已经用锌叠氮化物、硫氰酸锌或锌N，N-二甲基二硫代氨基甲酸酯通过Mitsunobu反应成功地对1,2-O-异丙基-α-D-木糖呋喃糖（1）和1,2-O-异丙基-α-D-核糖呋喃糖（2）进行了。对于2，反应在C-5位置选择性地给出了所需产物，且收率良好（60-65%）。然而，将相同的反应条件应用于1，则主要形成了环状3,5-缩水衍生物。相反，将叠氮酸与1反应得到了5-叠氮基-5-去氧-1,2-O-异丙基-α-D-木糖呋喃糖，以及前所未知的5-叠氮基-3,5-二去氧-1,2-O-异丙基-α-D-甘油-3-烯酮呋喃糖和3,5-二叠氮基-3,5-二去氧-1,2-O-异丙基-α-D-核糖呋喃糖；产率取决于反应时间和试剂的摩尔比。

  DOI：

  10.1135/cccc20001745

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。
• (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。
• 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.
• Carbohydrate triazole tethered 2-pyridyl-benzimidazole ligands: Synthesis of their palladium (II) complexes and antimicrobial activities
  作者：Sadanala Bhavya Deepthi、Pambala Ramesh、Rajiv Trivedi、Sudheer Kumar Buddana、Reddy Shetty Prakasham

  DOI：10.1016/j.ica.2015.06.027

  日期：2015.8

  A series of carbohydrate-tethered 1-triazolyl-2-pyridyl-benzimidazole ligands have been prepared and the antimicrobial activity of their Pd(II) complexes has been studied. The alkyne, 1-propargyl-2-pyridyl- benzimidazole (2) was synthesized by the reaction of 2-pyridyl-benzimidazole and propargyl bromide in the presence of sodium hydride. The carbohydrate triazoles (4a-e) were synthesized by the Huisgen 1,3-dipolar cycloaddition reaction of alkyne (2) and different carbohydrate azides (3a-e). For comparative studies, benzyl triazole ligand (4f) was also synthesized. The palladium complexes (5a-f and 6), obtained from the reaction of the ligands (4a-f and 2 respectively) and Pd(COD) Cl-2 (1:1 ratio) in dichloromethane solution, were characterized by NMR, mass and elemental analysis. All the ligands and metal complexes were tested for the antibacterial activity against Gram positive and Gram negative bacterial strains. In this study, the ligands have displayed superior antimicrobial activity as compared to their corresponding metal complexes. (C) 2015 Elsevier B.V. All rights reserved.