1,1'-O-2,2',3,3',4,4',6,6'-tetrakis(3,4,5-trihydroxybenzoyl)-β,β'-D,D'-glucopyranosylbiphenyl-4,4'-diester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1,1'-O-2,2',3,3',4,4',6,6'-tetrakis(3,4,5-trihydroxybenzoyl)-β,β'-D,D'-glucopyranosylbiphenyl-4,4'-diester
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]-6-[4-[4-[(2S,3R,4S,5R,6R)-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-2-yl]oxycarbonylphenyl]benzoyl]oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• 化学式: C₈₂H₆₂O₄₆
• 分子量: 1783.37
• InChiKey: PAXMJXLSXTULPW-ILDNYHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  128
• 可旋转键数：
  33
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  767
• 氢给体数：
  24
• 氢受体数：
  46

反应信息

• 作为产物：
  描述：

  4,4'-苯偶酰氯 、 2,3,4,6-tetrakis(34,5-tribenzyloxybenzoyl)-D-glucose 在 palladium on activated charcoal 三乙胺 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 58.0h， 以20 mg的产率得到1,1'-O-2,2',3,3',4,4',6,6'-tetrakis(3,4,5-trihydroxybenzoyl)-β,β'-D,D'-glucopyranosylbiphenyl-4,4'-diester
  参考文献：
  名称：

  In vitro and in vivo inhibition of LPS-induced tumor necrosis factor-α production by dimeric gallotannin analogues

  摘要：

  Designed dimeric gallotannin analogues featuring two tetragalloylglucopyranose cores connected by various hydrocarbon linkers inhibit tumor necrosis factor-alpha secretion from lipopolysaccharide-stimulated human peripheral blood mononuclear cells by up to 53% (5-24 muM concentration range) compared to control. Comparable suppression of tumor necrosis factor-alpha levels (similar to 50% vs control) was observed in the plasma of rats co-treated with lipopolysaccharide and specific tannin analogues selected for their lack of interleukin 1-beta stimulating activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00251-6

文献信息

• In vitro and in vivo inhibition of LPS-induced tumor necrosis factor-α production by dimeric gallotannin analogues
  作者：Ken S Feldman、Sarah L Wilson、Michael D Lawlor、Charles H Lang、William J Scheuchenzuber

  DOI：10.1016/s0968-0896(01)00251-6

  日期：2002.1

  Designed dimeric gallotannin analogues featuring two tetragalloylglucopyranose cores connected by various hydrocarbon linkers inhibit tumor necrosis factor-alpha secretion from lipopolysaccharide-stimulated human peripheral blood mononuclear cells by up to 53% (5-24 muM concentration range) compared to control. Comparable suppression of tumor necrosis factor-alpha levels (similar to 50% vs control) was observed in the plasma of rats co-treated with lipopolysaccharide and specific tannin analogues selected for their lack of interleukin 1-beta stimulating activity. (C) 2001 Elsevier Science Ltd. All rights reserved.