3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-5-(4-(2-pyridyl)-1H-1,2,3-triazole-1-yl)-α-D-xylofuranose | 1613038-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-5-(4-(2-pyridyl)-1H-1,2,3-triazole-1-yl)-α-D-xylofuranose
• 英文别名: [(3aR,5R,6S,6aR)-2,2-dimethyl-5-[(4-pyridin-2-yltriazol-1-yl)methyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 1613038-62-2
• 化学式: C₂₂H₂₂N₄O₅
• 分子量: 422.44
• InChiKey: MTDMEWIKZOHGHC-RCLSDMTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-5-(4-(2-pyridyl)-1H-1,2,3-triazole-1-yl)-α-D-xylofuranose 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到[Pd(3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-5-(4-(2-pyridyl)-1H-1,2,3-triazole-1-yl)-α-D-xylofuranose)Cl₂]
  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：

  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

文献信息

• 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.