[1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-β-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine | 866784-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-β-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine
• 英文别名: glucosimide-PAF；[(2R)-2-[(2R,3R,4R,5S,6R)-3-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 866784-44-3
• 化学式: C₃₈H₇₁N₂O₁₂P
• 分子量: 778.962
• InChiKey: RALIAYBWJFPSIR-GBCGRDLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  30
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-β-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine 在 sodium hydroxide 、 盐酸 、 乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以63%的产率得到[1-O-octadecyl-2-O-(2'-deoxy-2'-amino-β-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine hydrochloride
  参考文献：
  名称：

  Glucosamine-glycerophospholipids That Activate Cell-Matrix Adhesion and Migration

  摘要：

  Two new analogues derived from the platelet activating factor (PAF), containing glucosamine instead of the acetyl group, were synthesized, and their effect on the human keratinocyte cell line HaCaT was evaluated with respect to cytotoxicity, proliferation, adhesion, and migration. Starting with (R)-1,2-isopropylideneglycerol (3), the glycosylation acceptor 1-O-octadecyl-3-O-tert-butyldimethylsilyl-sn-glycerol (6) was synthesized in three steps. Glycosylation of 6 with the already known O-(3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-beta-D-glycopyranosyl)trichloracetimidate gave 1-O-octadecyl-2-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-dimethylmaleimido-beta-D-glucopyranosyl)-3-O-tert-butyldimethylsilyl-sn-glycerol (7). After removing the (tert-butyldimethyl)silyl (TBDMS) group with FeCl3 center dot 6H(2)O, phosphoryl choline was introduced, yielding [1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-beta-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine (2) (glucosimide-PAF). pH controlled cleavage of the amino protection group gave [1-O-octadecyl-2-O-(2'-deoxy-2'-amino-beta-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine hydrochloride (1) (glucosamine-PAF). 2 inhibited proliferation of HaCaT cells by 26% at nontoxic concentrations, while 1 increased the proliferation rate by 30% at low concentrations. At higher concentrations, both compounds showed cytotoxic properties with LD50 = 30 mu mol/L (1) and LD50 = 5-6 mu mol/L (2). Both 1 and 2 were potent promoters of cell adhesion and migration of HaCaT cells.

  DOI：

  10.1021/jm050558n
• 作为产物：
  描述：

  硬脂基溴 在 吡啶 、 咪唑 、 三氟甲磺酸三甲基硅酯 、 三氯化铁 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 20.5h， 生成 [1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-β-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine
  参考文献：
  名称：

  Glucosamine-glycerophospholipids That Activate Cell-Matrix Adhesion and Migration

  摘要：

  Two new analogues derived from the platelet activating factor (PAF), containing glucosamine instead of the acetyl group, were synthesized, and their effect on the human keratinocyte cell line HaCaT was evaluated with respect to cytotoxicity, proliferation, adhesion, and migration. Starting with (R)-1,2-isopropylideneglycerol (3), the glycosylation acceptor 1-O-octadecyl-3-O-tert-butyldimethylsilyl-sn-glycerol (6) was synthesized in three steps. Glycosylation of 6 with the already known O-(3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-beta-D-glycopyranosyl)trichloracetimidate gave 1-O-octadecyl-2-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-dimethylmaleimido-beta-D-glucopyranosyl)-3-O-tert-butyldimethylsilyl-sn-glycerol (7). After removing the (tert-butyldimethyl)silyl (TBDMS) group with FeCl3 center dot 6H(2)O, phosphoryl choline was introduced, yielding [1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-beta-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine (2) (glucosimide-PAF). pH controlled cleavage of the amino protection group gave [1-O-octadecyl-2-O-(2'-deoxy-2'-amino-beta-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine hydrochloride (1) (glucosamine-PAF). 2 inhibited proliferation of HaCaT cells by 26% at nontoxic concentrations, while 1 increased the proliferation rate by 30% at low concentrations. At higher concentrations, both compounds showed cytotoxic properties with LD50 = 30 mu mol/L (1) and LD50 = 5-6 mu mol/L (2). Both 1 and 2 were potent promoters of cell adhesion and migration of HaCaT cells.

  DOI：

  10.1021/jm050558n

文献信息

• Glucosamine-glycerophospholipids That Activate Cell-Matrix Adhesion and Migration
  作者：Thilo Bartolmäs、Tabea Heyn、Michael Mickeleit、Annette Fischer、Werner Reutter、Kerstin Danker

  DOI：10.1021/jm050558n

  日期：2005.10.1

  Two new analogues derived from the platelet activating factor (PAF), containing glucosamine instead of the acetyl group, were synthesized, and their effect on the human keratinocyte cell line HaCaT was evaluated with respect to cytotoxicity, proliferation, adhesion, and migration. Starting with (R)-1,2-isopropylideneglycerol (3), the glycosylation acceptor 1-O-octadecyl-3-O-tert-butyldimethylsilyl-sn-glycerol (6) was synthesized in three steps. Glycosylation of 6 with the already known O-(3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-beta-D-glycopyranosyl)trichloracetimidate gave 1-O-octadecyl-2-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-dimethylmaleimido-beta-D-glucopyranosyl)-3-O-tert-butyldimethylsilyl-sn-glycerol (7). After removing the (tert-butyldimethyl)silyl (TBDMS) group with FeCl3 center dot 6H(2)O, phosphoryl choline was introduced, yielding [1-O-octadecyl-2-O-(2'-deoxy-2'-dimethylmaleimido-beta-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine (2) (glucosimide-PAF). pH controlled cleavage of the amino protection group gave [1-O-octadecyl-2-O-(2'-deoxy-2'-amino-beta-D-glucopyranosyl)-sn-glycero(3)]phosphorylcholine hydrochloride (1) (glucosamine-PAF). 2 inhibited proliferation of HaCaT cells by 26% at nontoxic concentrations, while 1 increased the proliferation rate by 30% at low concentrations. At higher concentrations, both compounds showed cytotoxic properties with LD50 = 30 mu mol/L (1) and LD50 = 5-6 mu mol/L (2). Both 1 and 2 were potent promoters of cell adhesion and migration of HaCaT cells.