oleyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1332704-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: oleyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(Z)-octadec-9-enoxy]oxan-3-yl]acetamide
• CAS: 1332704-64-9
• 化学式: C₂₆H₄₉NO₆
• 分子量: 471.678
• InChiKey: PYJNULFKLXWZOE-LZDNSSROSA-N

物化性质

• 熔点：
  155-160 °C
• 沸点：
  659.9±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  oleyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 Jack bean N-acetyl-β-D-glucosaminidase 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 生成 D-GlcNAc
  参考文献：
  名称：

  Synthesis of Antimitotic Thioglycosides: In Vitro and in Vivo Evaluation of Their Anticancer Activity

  摘要：

  The synthesis and biological activity of oleylN-acetyl-alpha- and beta-n-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the a-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.

  DOI：

  10.1021/jm200961q
• 作为产物：
  描述：

  油醇 在 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 27.17h， 生成 oleyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Antimitotic Thioglycosides: In Vitro and in Vivo Evaluation of Their Anticancer Activity

  摘要：

  The synthesis and biological activity of oleylN-acetyl-alpha- and beta-n-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the a-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.

  DOI：

  10.1021/jm200961q

文献信息

• Micellar nanoparticles containing antitumoral glycosides
  申请人：Fundación Centro Nacional de Investigaciones Cardiovasculares Carlos III (CNIC)

  公开号：EP2921179A1

  公开（公告）日：2015-09-23

  The present invention is related to micelles which comprise nanoparticles having a core selected from the group consisting of iron oxide, UCNP and a metal, and a hydrophobic outer layer, and a coating thereon comprising glycoside derivatives, a process for their preparation and uses thereof.

  本发明涉及胶束，胶束由纳米颗粒组成，纳米颗粒的核心选自氧化铁、UCNP 和金属组成的组，外层为疏水性，胶束上有一层由糖苷衍生物组成的涂层，本发明还涉及胶束的制备方法及其用途。
• Synthesis of Antimitotic Thioglycosides: In Vitro and in Vivo Evaluation of Their Anticancer Activity
  作者：Isabel García-Álvarez、Hugo Groult、Josefina Casas、M. Asunción Barreda-Manso、Natalia Yanguas-Casás、Manuel Nieto-Sampedro、Lorenzo Romero-Ramírez、Alfonso Fernández-Mayoralas

  DOI：10.1021/jm200961q

  日期：2011.10.13

  The synthesis and biological activity of oleylN-acetyl-alpha- and beta-n-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the a-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.