1-O-hexadecyl-2-O-methyl-3-S-(α-D-1'-thioglucopyranosyl)-sn-glycerol | 129176-43-8

• 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-S-(α-D-1'-thioglucopyranosyl)-sn-glycerol
• 英文别名: 1-O-hexadecyl-2-O-methyl-3-S-α-D-glucopyranosyl-sn-glycerol；(2R,3R,4S,5S,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropyl]sulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 129176-43-8
• 化学式: C₂₆H₅₂O₇S
• 分子量: 508.761
• InChiKey: KMNKDRDLSLQCIW-JMLBKQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 barium(II) oxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.0h， 生成 1-O-hexadecyl-2-O-methyl-3-S-(α-D-1'-thioglucopyranosyl)-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

文献信息

• A short synthesis of antitumor ether thioglycolipids: Thioglycosidation of a glucose donor with a tributylstannyl sulfide acceptor
  作者：Hoe-Sup Byun、Robert Bittman

  DOI：10.1016/0040-4039(95)01015-a

  日期：1995.7

  Efficient routes to alpha- acid beta-thioglucolipids 1a and 1b are described starting from 1-O-hexadecyl-3-O-(p-toluenesulfonyl)-sn-glycerol (2) in 72% and 68% overall yields, respectively. Deprotection of the S-benzyl group of the glyceride 4 with tri-n-butyltin hydride produced the tin derivative 5, which was glycosidated with a glucose donor.
• 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：——
• Synthesis and antineoplastic properties of ether-linked thioglycolipids
  作者：Pedro N. Guivisdalsky、Robert Bittman、Zigrida Smith、Merle L. Blank、Fred Snyder、Sandra Howard、Hassan Salari

  DOI：10.1021/jm00171a042

  日期：1990.9

  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.