1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-sn-glycerol | 153952-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-sn-glycerol
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]oxan-2-yl]methyl acetate
• CAS: 153952-69-3
• 化学式: C₃₄H₆₁NO₁₁
• 分子量: 659.858
• InChiKey: DFSKYOCXUNBQFO-GOSYQUBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  46.0
• 可旋转键数：
  26.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  144.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 氢氧化钾 作用下， 反应 2.0h， 生成 1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and Evaluation of the Antiproliferative Effects of 1-O-Hexadecyl-2-O- methyl-3-O-(2‘-acetamido-2‘-deoxy-β-d-glucopyranosyl)-sn-glycerol and 1-O-Hexadecyl-2-O-methyl-3-O-(2‘-amino-2‘-deoxy-β-d-glucopyranosyl)-sn-glycerol on Epithelial Cancer Cell Growth

  摘要：

  Two ether glucosyl diglyceride analogs were synthesized, and their antiproliferative activity against four epithelial cancer cell lines was evaluated. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl) -sn-glycerol (4) was synthe sized by reaction of 2-acetamido-2-deoxy-3, 4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride with 1-O-hexadecyl-2-O-methyl-sn-glycerol followed by deacetylation by methanolic hydrolysis. The N-acetyl group of 4 was removed by hydrolysis with ethanolic potassium hydroxide to form 1-O-hexadecyl-2-O-methyl-3-O-(2'-amino-2'-deoxy-beta-D-glucopyranosyl) -sn-glycerol (5). Compounds 4 and 5 inhibited the proliferation of MCF-7, A549, A427, and T84 cancer cell lines. The IC50 values for 5 ranged from 6.5 to 12.2 mu M, whereas 4 was more effective against A549 cells (IC50 9 mu M) than against MCF-7 (IC50 17 mu M) and A427 (IC50 25 mu M) cells and was inactive against T84 cells. Under identical incubation conditions, compounds 4 and 5 were potent inhibitors of the proliferation of OVCAR-3 cells with IC50 values of 12 and 4 mu M, respectively, whereas ET-18-OCH3, hexadecylphosphocholine, and erucylphosphocholine had IC50 values of 24, >30, and >30 mu M, respectively. The cell-inhibitory profile of these ether-linked glucosyl diglycerides strengthens the hypothesis that such glycolipids represent a distinct group of antitumor ether lipids, having antineoplastic activities that differ from the well-known alkylphosphocholines and alkyllysophospholipids.

  DOI：

  10.1021/jm950928f
• 作为产物：
  描述：

  十六基甲基甘油 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 三苯基氯甲烷 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and Evaluation of the Antiproliferative Effects of 1-O-Hexadecyl-2-O- methyl-3-O-(2‘-acetamido-2‘-deoxy-β-d-glucopyranosyl)-sn-glycerol and 1-O-Hexadecyl-2-O-methyl-3-O-(2‘-amino-2‘-deoxy-β-d-glucopyranosyl)-sn-glycerol on Epithelial Cancer Cell Growth

  摘要：

  Two ether glucosyl diglyceride analogs were synthesized, and their antiproliferative activity against four epithelial cancer cell lines was evaluated. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl) -sn-glycerol (4) was synthe sized by reaction of 2-acetamido-2-deoxy-3, 4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride with 1-O-hexadecyl-2-O-methyl-sn-glycerol followed by deacetylation by methanolic hydrolysis. The N-acetyl group of 4 was removed by hydrolysis with ethanolic potassium hydroxide to form 1-O-hexadecyl-2-O-methyl-3-O-(2'-amino-2'-deoxy-beta-D-glucopyranosyl) -sn-glycerol (5). Compounds 4 and 5 inhibited the proliferation of MCF-7, A549, A427, and T84 cancer cell lines. The IC50 values for 5 ranged from 6.5 to 12.2 mu M, whereas 4 was more effective against A549 cells (IC50 9 mu M) than against MCF-7 (IC50 17 mu M) and A427 (IC50 25 mu M) cells and was inactive against T84 cells. Under identical incubation conditions, compounds 4 and 5 were potent inhibitors of the proliferation of OVCAR-3 cells with IC50 values of 12 and 4 mu M, respectively, whereas ET-18-OCH3, hexadecylphosphocholine, and erucylphosphocholine had IC50 values of 24, >30, and >30 mu M, respectively. The cell-inhibitory profile of these ether-linked glucosyl diglycerides strengthens the hypothesis that such glycolipids represent a distinct group of antitumor ether lipids, having antineoplastic activities that differ from the well-known alkylphosphocholines and alkyllysophospholipids.

  DOI：

  10.1021/jm950928f

文献信息

• Preparation of ether-linked 2-acetamido-2-deoxy β-glycolipids via zinc chloride promoted coupling of Ac4GlcNAcCl with lipid hydroxy groups
  作者：Erukulla Ravi Kumar、Hoe-Sup Byun、Sihe Wang、Robert Bittman

  DOI：10.1016/s0040-4039(00)75823-0

  日期：1994.1

  Stereoselective glycosidation of lipid hydroxy groups has been achieved using 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glycosyl chloride as the glycosyl donor in CH2Cl2. In the presence of ZnCl2 (1 equiv.) and various ''promoters'' (1 equiv.) such as Ph(3)CCl, 18-crown-6/KCl, n-Bu(4)NBr, or Me(3)SiCl, beta-glycolipid conjugates are formed as the initial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl2 in CH2Cl2.