1-O-hexadecyl-2-O-methyl-sn-glycero-3-O-β-D-glucopyranoside 2,3,4,6-tetraacetate | 110576-89-1

• 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: 1-O-hexadecyl-2-O-methyl-sn-glycero-3-O-β-D-glucopyranoside 2,3,4,6-tetraacetate
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]oxan-2-yl]methyl acetate
• CAS: 110576-89-1
• 化学式: C₃₄H₆₀O₁₂
• 分子量: 660.843
• InChiKey: HWYLSBVHQBXZOI-GEPQNFMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 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：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-2-O-methyl-sn-glycero-3-O-β-D-glucopyranoside 2,3,4,6-tetraacetate 在 甲醇 、 sodium hydroxide 作用下， 以100%的产率得到1-O-hexadecyl-2-O-methyl-3-O-(β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and antineoplastic properties of ether-linked thioglycolipids

  摘要：

  Ether-linked glycero-alpha- and beta-D-glucopyranosides and glycero-1-thio-alpha- and beta-D-glucopyranosides have been synthesized by modifications of the Königs-Knorr procedure, and their antitumor activities have been evaluated. The bioactivities of these compounds have been evaluated in five different cell lines (WEHI 3B, C653, X63/OMIL3, R6X-B15, and HL-60) and compared with the activities of 1-O-hexadecyl-2-O-methyl-sn-3-glycerophosphocholine (GPC) and its enantiomer, 3-O-hexadecyl-2-O-methyl-sn-1-GPC. The results indicate that a alpha-D-thioglucopyranoside [1-O-hexadecyl-2-O-methyl-3-S-(alpha-D-1'- thioglucopyranosyl-sn-glycerol)] is selective with respect to its action on target cells, with high activity for killing of WEHI 3B and C653 cells as determined by inhibition of [3H]thymidine incorporation into DNA and HL-60 cell cytotoxicity, but unable to induce aggregation of rabbit platelets at 10(-5) M. The corresponding beta-linked thioglycolipid was ineffective with respect to cytotoxicity against each cell line tested, indicating the importance of configuration at the anomeric position; the beta-thioglycoside was also ineffective with respect to inducing platelet aggregation. 1-O-Hexadecyl-2-O-methyl-sn-3-GPC and 3-O-hexadecyl-2-O-methyl-sn-1-GPC were potent inhibitors of growth of each cell line tested but also caused rabbit platelet aggregation at concentrations greater than or equal to 10(-7) M. Thus, 3-S-(alpha-thioglycopyranosyl)-sn- glycerols bearing a long-chain O-alkyl group at the sn-1 position and a methoxy group at the sn-2 position of glycerol appear to be a promising class of antineoplastic agents with lower risk of inducing thrombosis than the widely studied platelet activating factor analogue, 1-O-octadecyl-2-O-methyl-rac-3-GPC.

  DOI：

  10.1021/jm00171a042
• 作为产物：
  描述：

  十六基甲基甘油 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 氰化汞 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 24.0h， 以85%的产率得到1-O-hexadecyl-2-O-methyl-sn-glycero-3-O-β-D-glucopyranoside 2,3,4,6-tetraacetate
  参考文献：
  名称：

  Synthesis and antineoplastic properties of ether-linked thioglycolipids

  摘要：

  Ether-linked glycero-alpha- and beta-D-glucopyranosides and glycero-1-thio-alpha- and beta-D-glucopyranosides have been synthesized by modifications of the Königs-Knorr procedure, and their antitumor activities have been evaluated. The bioactivities of these compounds have been evaluated in five different cell lines (WEHI 3B, C653, X63/OMIL3, R6X-B15, and HL-60) and compared with the activities of 1-O-hexadecyl-2-O-methyl-sn-3-glycerophosphocholine (GPC) and its enantiomer, 3-O-hexadecyl-2-O-methyl-sn-1-GPC. The results indicate that a alpha-D-thioglucopyranoside [1-O-hexadecyl-2-O-methyl-3-S-(alpha-D-1'- thioglucopyranosyl-sn-glycerol)] is selective with respect to its action on target cells, with high activity for killing of WEHI 3B and C653 cells as determined by inhibition of [3H]thymidine incorporation into DNA and HL-60 cell cytotoxicity, but unable to induce aggregation of rabbit platelets at 10(-5) M. The corresponding beta-linked thioglycolipid was ineffective with respect to cytotoxicity against each cell line tested, indicating the importance of configuration at the anomeric position; the beta-thioglycoside was also ineffective with respect to inducing platelet aggregation. 1-O-Hexadecyl-2-O-methyl-sn-3-GPC and 3-O-hexadecyl-2-O-methyl-sn-1-GPC were potent inhibitors of growth of each cell line tested but also caused rabbit platelet aggregation at concentrations greater than or equal to 10(-7) M. Thus, 3-S-(alpha-thioglycopyranosyl)-sn- glycerols bearing a long-chain O-alkyl group at the sn-1 position and a methoxy group at the sn-2 position of glycerol appear to be a promising class of antineoplastic agents with lower risk of inducing thrombosis than the widely studied platelet activating factor analogue, 1-O-octadecyl-2-O-methyl-rac-3-GPC.

  DOI：

  10.1021/jm00171a042

文献信息

• GUIVISDALSKY, PEDRO N.;BITTMAN, ROBETR;SMITH, ZIGRIDA;BLANK, MERLE L.;SNY+, J. MED. CHEM., 33,(1990) N, C. 2614-2621
  作者：GUIVISDALSKY, PEDRO N.、BITTMAN, ROBETR、SMITH, ZIGRIDA、BLANK, MERLE L.、SNY+

  DOI：——

  日期：——