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1-deoxy-1-{[(2,4-dichlorophenoxy)acetyl]amino}-β-D-glucopyranuronic acid

中文名称
——
中文别名
——
英文名称
1-deoxy-1-{[(2,4-dichlorophenoxy)acetyl]amino}-β-D-glucopyranuronic acid
英文别名
1-deoxy-1-{[(2,4-dichlorophenoxy)acethyl]amino}-β-D-glucopyranuronic acid;(2S,3S,4S,5R,6R)-6-[[2-(2,4-dichlorophenoxy)acetyl]amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
1-deoxy-1-{[(2,4-dichlorophenoxy)acetyl]amino}-β-D-glucopyranuronic acid化学式
CAS
——
化学式
C14H15Cl2NO8
mdl
——
分子量
396.181
InChiKey
BFHMOZXCVLWXJK-IEECTRCBSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.6
  • 重原子数:
    25
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.43
  • 拓扑面积:
    146
  • 氢给体数:
    5
  • 氢受体数:
    8

反应信息

  • 作为产物:
    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
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文献信息

  • [EN] DIFFERENTIATION MODULATING AGENTS AND USES THEREFOR<br/>[FR] AGENTS DE MODULATION DE LA DIFFERENCIATION ET UTILISATIONS ASSOCIEES
    申请人:UNIV QUEENSLAND
    公开号:WO2005065686A1
    公开(公告)日:2005-07-21
    This invention discloses methods and agents for modulating the differentiation potential and/or proliferation of preadipocytes. More particularly, the present invention discloses methods and agents for modulating a fibroblast growth factor (FGF) signalling pathway, especially the FGF-1 or FGF-2 signalling pathway, for treating or preventing adiposity-related conditions including, but not limited to, obesity, lipoma and lipomatosis.
    该发明揭示了调节前脂肪细胞分化潜能和/或增殖的方法和药剂。更具体地,本发明揭示了调节成纤维细胞生长因子(FGF)信号通路的方法和药剂,特别是FGF-1或FGF-2信号通路,用于治疗或预防与脂肪相关的疾病,包括但不限于肥胖、脂肪瘤和脂肪增生。
  • Identification of novel inhibitors of fibroblast growth factor (FGF-2) binding to heparin and endothelial cell survival from a structurally diverse carbohybrid library
    作者:Paul V Murphy、Nigel Pitt、Alan O'Brien、Philomena M Enright、Amanda Dunne、Stephen J Wilson、Rhona M Duane、Kathy M O'Boyle
    DOI:10.1016/s0960-894x(02)00700-x
    日期:2002.11
    Inhibitors of FGF-2 binding to a heparin-albumin conjugate were identified by ELISA from a library of glucuronic acid derivatives. These compounds were also inhibitors of endothelial cell survival that is dependant on FGF-2 and heparin or heparan sulfate proteoglycans. The results indicate that these bioactive compounds may prove useful as lead structures for the further development of pharmaceutical agents capable of modulating biological activity of FGF-2. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth
    作者:Nigel Pitt、Rhona M. Duane、Alan O' Brien、Helena Bradley、Stephen J. Wilson、Kathy M. O' Boyle、Paul V. Murphy
    DOI:10.1016/j.carres.2004.05.024
    日期:2004.8
    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.
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