6,7'-gossypol diglucoside tetraacetate | 1337972-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7'-gossypol diglucoside tetraacetate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[11-[3,5-dihydroxy-10-methyl-7-propan-2-yl-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-11-yl]-3,6-dihydroxy-10-methyl-7-propan-2-yl-2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-5-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 1337972-83-4
• 化学式: C₅₈H₆₆O₂₆
• 分子量: 1179.15
• InChiKey: PFMGBJGCXHGWDA-AURSWVPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  84
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  347
• 氢给体数：
  4
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  6,7'-gossypol diglucoside tetraacetate 在 甲醇 、 sodium methylate 作用下， 生成 1,1',6,7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-6',7-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-[2,2'-binaphthalene]-8,8'-dicarbaldehyde
  参考文献：
  名称：

  Novel O-glycosidic gossypol isomers and their bioactivities

  摘要：

  Novel glycosidic gossypol analogs, 7,7'-gossypol diglucoside tetraacetate GS1, 6,7'-gossypol diglucoside tetraacetate GS2, 7,7'-gossypol diglycoside GS1', 6,7'-gossypol diglycoside GS2' were obtained by the ultrasound-assisted reaction of the potassium salt of gossypol with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide under PTC conditions and were fully characterized by 1D NMR ((1)H NMR, (13)C NMR, DEPT, 1D NOE), 2D NMR (HMBC, HMQC), FTIR, HRMS and HPLC. The anticancer activities, cytotoxic effects as well as anti-trypanosomal activities of these novel glycosidic gossypols were explored and suggest that gossypol glycosides could be used to develop new candidates for anticancer drugs and anti-trypanosomal agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.06.031
• 作为产物：
  描述：

  (-)-棉子素 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 6.0h， 以36%的产率得到7,7'-gossypol diglucoside tetraacetate
  参考文献：
  名称：

  Novel O-glycosidic gossypol isomers and their bioactivities

  摘要：

  Novel glycosidic gossypol analogs, 7,7'-gossypol diglucoside tetraacetate GS1, 6,7'-gossypol diglucoside tetraacetate GS2, 7,7'-gossypol diglycoside GS1', 6,7'-gossypol diglycoside GS2' were obtained by the ultrasound-assisted reaction of the potassium salt of gossypol with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide under PTC conditions and were fully characterized by 1D NMR ((1)H NMR, (13)C NMR, DEPT, 1D NOE), 2D NMR (HMBC, HMQC), FTIR, HRMS and HPLC. The anticancer activities, cytotoxic effects as well as anti-trypanosomal activities of these novel glycosidic gossypols were explored and suggest that gossypol glycosides could be used to develop new candidates for anticancer drugs and anti-trypanosomal agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.06.031