N-甲基-beta-D-吡喃葡萄糖基胺盐酸盐(1:1) | 114761-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-甲基-beta-D-吡喃葡萄糖基胺盐酸盐(1:1)
• 英文名称: N-methyl-β-D-glucopyranosylamine
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(methylamino)oxane-3,4,5-triol
• CAS: 114761-39-6
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: HJFJVGRAUAAGDP-XUUWZHRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-噻吩甲酰氯 、 N-甲基-beta-D-吡喃葡萄糖基胺盐酸盐(1:1) 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以63%的产率得到N-(β-D-glucopyranosyl)-N-methyl-2-thiophenecarboxamide
  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：

  葡萄糖 、 甲胺 反应 16.0h， 生成 N-甲基-beta-D-吡喃葡萄糖基胺盐酸盐(1:1)
  参考文献：
  名称：

  Compositions comprising glycosylamide surfactants

  摘要：

  本发明涉及一种包含糖基酰胺表面活性剂的新型洗涤剂和/或个人清洁组合物。

  公开号：

  US05872111A1

文献信息

• Novel compounds
  申请人：Nomura Sumihiro

  公开号：US20070060545A1

  公开（公告）日：2007-03-15

  A compound of the formula: wherein Ring A and Ring B are (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, wherein —NR— group and —CH 2 — group are both on the same ring of the unsaturated fused heterobicyclic ring, and Ring B is an optionally substituted monocyclic unsaturated heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; and R is a hydrogen atom, a lower alkyl group, a lower alkanoyl group or a lower alkoxycarbonyl group, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  该化合物的化学式为：其中环A和环B分别为（1）环A为可选取代的不饱和单环杂环，环B为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A为可选取代的苯环，环B为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，或（3）环A为可选取代的不饱和融合杂双环，其中—NR—基团和—CH2—基团均位于不饱和融合杂双环的同一环上，环B为可选取代的单环不饱和杂环、可选取代的不饱和融合杂双环或可选取代的苯环；R为氢原子、低碳基、低烷酰基或低烷氧羰基基团，或其药学上可接受的盐或前药。
• Biological applications of semiconductor nanocrystals
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP0990903A1

  公开（公告）日：2000-04-05

  The present invention provides a composition comprising fluorescent semiconductor nanocrystals associated to a compound, wherein the nanocrystals have a characteristic spectral emission, wherein said spectral emission is tunable to a desired wavelength by controlling the size of the nanocrystal, and wherein said emission provides information about a biological state or event.

  本发明提供了一种包含与化合物相关联的荧光半导体纳米晶体的组合物，其中纳米晶体具有特征光谱发射，所述光谱发射可通过控制纳米晶体的大小调谐到所需波长，并且所述发射可提供有关生物状态或事件的信息。
• The structure of glycosyl amides: A combined study by NMR spectroscopy, X-ray crystallography, and computational chemistry
  作者：Martín Avalos、Reyes Babiano、María J. Carretero、Pedro Cintas、Francisco J. Higes、JoséL. Jiménez、Juan C. Palacios

  DOI：10.1016/s0040-4020(97)10321-0

  日期：1998.1

  The structure of N-formyl, N-acetyl-N-methyl, and N-acetyl glycosylamines has been studied by NMR spectroscopy in solution, single crystal X-ray diffractometry, and corroborated by PM3 semiempirical calculations. The results quite agree with an anti conformation around the glycosydic bond for these substances. (C) 1997 Elsevier Science Ltd. All rights reserved.
• FLUORINATED 2-NITROIMIDAZOLE ANALOGS FOR DETECTING HYPOXIC TUMOR CELLS
  申请人：SRI INTERNATIONAL

  公开号：EP0775117A1

  公开（公告）日：1997-05-28
• WATER-SOLUBLE FLUORESCENT SEMICONDUCTOR NANOCRYSTALS
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1116036B1

  公开（公告）日：2004-08-11