(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(1H-indole-2-carbonyl)-amino]-tetrahydro-pyran-2-carboxylic acid methyl ester | 755023-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(1H-indole-2-carbonyl)-amino]-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 755023-83-7
• 化学式: C₂₂H₂₄N₂O₁₀
• 分子量: 476.44
• InChiKey: HZMAMYCKMFAUTF-ZFORQUDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  159.32
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(1H-indole-2-carbonyl)-amino]-tetrahydro-pyran-2-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以10%的产率得到1-deoxy-1-[(1H-indol-2-ylcarbonyl)amino]-β-D-glucopyranuronic acid
  参考文献：
  名称：

  Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth

  摘要：

  Compounds that alter endothelial cell growth are of interest in the development of angiogenesis modulators. A structurally diverse series of saccharide derivatives (glycosylamide conjugates) have been synthesized and evaluated for their effects on bovine aortic endothelial cell (BAEC) growth. Heparin-albumin (HA) reduced BAEC growth by 32% at 10 mug/mL and a number of the novel saccharide conjugates from the library were found to mimic the effect of HA as they also inhibit endothelial cell survival under identical conditions. Two thiophene conjugates, thioglucamide (24% inhibition at 35 muM) and a related glucuronide (26% inhibition at 33 muM) were the most potent inhibitors of BAEC growth, as determined using a methylthiazol tetrazoliurn (MTT) assay. The effects of thioglucamide and HA on absolute cell number were also studied using cell counting experiments; thioglucamide (47% after 24 h) was more potent than indicated by the MTT assay and initially reduced the BAEC number to a greater extent than HA (30% after 24 h); however, its actions were over more rapidly than were HA's as cell growth had returned to levels of the control after 72 h where HA still caused 25% inhibition. The binding of the monosaccharide conjugates to fibroblast growth factor (FGF-2) in competition with heparin-alburnin by ELISA was investigated to establish the possible mechanism by which glycoconjugates could alter growth but there was no general correlation between reduction in viable cell population and binding to FGF-2. No glycoconjugate reduced the proliferation of mouse mammary epithelial cells, nor did any alter gross cell morphology, supporting a proposal that the reduction in BAEC survival by monosaccharide conjugates such as thioglucamide is a result of the inhibition of cell proliferation rather than being an induction of cytotoxicity. These studies indicate that cell biological studies to determine the mechanism of action of the simple monosaccharide conjugates may be worthwhile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.024
• 作为产物：
  描述：

  1-叠氮基-1-脱氧-D-半乳糖醛酸酯2,3,4-三乙酸酯甲酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(1H-indole-2-carbonyl)-amino]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth

  摘要：

  Compounds that alter endothelial cell growth are of interest in the development of angiogenesis modulators. A structurally diverse series of saccharide derivatives (glycosylamide conjugates) have been synthesized and evaluated for their effects on bovine aortic endothelial cell (BAEC) growth. Heparin-albumin (HA) reduced BAEC growth by 32% at 10 mug/mL and a number of the novel saccharide conjugates from the library were found to mimic the effect of HA as they also inhibit endothelial cell survival under identical conditions. Two thiophene conjugates, thioglucamide (24% inhibition at 35 muM) and a related glucuronide (26% inhibition at 33 muM) were the most potent inhibitors of BAEC growth, as determined using a methylthiazol tetrazoliurn (MTT) assay. The effects of thioglucamide and HA on absolute cell number were also studied using cell counting experiments; thioglucamide (47% after 24 h) was more potent than indicated by the MTT assay and initially reduced the BAEC number to a greater extent than HA (30% after 24 h); however, its actions were over more rapidly than were HA's as cell growth had returned to levels of the control after 72 h where HA still caused 25% inhibition. The binding of the monosaccharide conjugates to fibroblast growth factor (FGF-2) in competition with heparin-alburnin by ELISA was investigated to establish the possible mechanism by which glycoconjugates could alter growth but there was no general correlation between reduction in viable cell population and binding to FGF-2. No glycoconjugate reduced the proliferation of mouse mammary epithelial cells, nor did any alter gross cell morphology, supporting a proposal that the reduction in BAEC survival by monosaccharide conjugates such as thioglucamide is a result of the inhibition of cell proliferation rather than being an induction of cytotoxicity. These studies indicate that cell biological studies to determine the mechanism of action of the simple monosaccharide conjugates may be worthwhile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.024