2-O-(2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranosyl)-sn-glycerol | 250608-18-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-O-(2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranosyl)-sn-glycerol
• 英文别名: 2-O-(2,3,4,6-tetra-O-(chloroacetyl)-β-D-glucopyranosyl)-glycerol
• CAS: 250608-18-5
• 化学式: C₁₇H₂₂Cl₄O₁₂
• 分子量: 560.166
• InChiKey: NWRVVAZNUVIYTA-OBCKKKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  164.12
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-O-(2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranosyl)-sn-glycerol 在 吡啶 、 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 1,3-Di-O-decanoyl-2-O-β-D-glucopyranosyl-sn-glycerol
  参考文献：
  名称：

  与葡萄糖醛酸二酰基甘油相关的阴离子糖脂可抑制蛋白激酶Akt。

  摘要：

  基于2-O-β-D-吡喃葡萄糖基-sn-甘油支架并带有一个或两个不同长度的酰基链的新葡糖醛酸二酰基甘油（GlcADG）类似物已被合成为靶向蛋白激酶Akt的3-磷酸磷脂酰肌醇（PI3P）模拟物。 。使用体外激酶测定法测定了所制备化合物的Akt抑制作用。在人卵巢癌IGROV-1细胞系中测试了该化合物的抗增殖活性，在其中我们发现其中两个可以抑制增殖，并与靶标抑制作用保持一致。

  DOI：

  10.1039/c4ob01602e
• 作为产物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranosyl)-sn-glycerol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到2-O-(2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol

  摘要：

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

  DOI：

  10.1016/s0968-0896(99)00137-6

文献信息

• 2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation
  作者：Milind Dangate、Laura Franchini、Fiamma Ronchetti、Takanari Arai、Akira Iida、Harukuni Tokuda、Diego Colombo

  DOI：10.1016/j.bmc.2009.06.064

  日期：2009.8

  New sulfoquinovosyldiacylglycerols derived from 2-O-beta-D-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). (C) 2009 Elsevier Ltd. All rights reserved.