C-(2,3,4,6-tetra-O-benzoyl-1-hydroxy-β-D-glucopyranosyl)formamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(2,3,4,6-tetra-O-benzoyl-1-hydroxy-β-D-glucopyranosyl)formamide
• 英文别名: 3,4,5,7-tetra-O-benzoyl-α-D-gluco-heptulopyranosonamide；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-carbamoyl-6-hydroxyoxan-2-yl]methyl benzoate
• 化学式: C₃₅H₂₉NO₁₁
• 分子量: 639.615
• InChiKey: GJBCBUOBMGMGAI-CPXFVOFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-戊酮 、 C-(2,3,4,6-tetra-O-benzoyl-1-hydroxy-β-D-glucopyranosyl)formamide 在 三氟甲磺酸 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到(1'S)-2',3',4',6'-tetra-O-benzoyl-1',5'-anhydro-D-glucitolspiro-[1',5]-2,2-diethyl-oxazolidin-4-one
  参考文献：
  名称：

  通过溶剂掺入的异头螺环：O-过酰化的（糖吡喃糖和溴吡喃糖基溴化物）onamide衍生物与酮的反应。

  摘要：

  在银（I）盐促进剂存在下，O-全乙酰化（α-D-半乳糖-庚基吡喃糖基溴）酰胺和O-过苯甲酰化（α-D-葡萄糖-庚基吡喃糖基溴）酮与酮的反应得到相应的O-过酰基化的1 '，5'-脱水-D-糖醇-螺-[1'，5] -4-亚氨基-2，2-二取代-1，3-二氧戊环。D-半乳糖构型的起始化合物提供了两个螺旋差向异构体，而D-葡萄糖相应物仅产生构型上的倒位产物。在酸性条件下，O-过苯甲酰化的α-D-葡萄糖-庚基吡咯烷酰胺和酮产生受保护的1'，5'-脱水-D-葡萄糖醇-螺-[1'，5] -2,2-二取代-恶唑烷-4-通过Zemplen方案O-去苯甲酰化的那些 这些化合物对兔肌肉糖原磷酸酶b没有抑制作用。

  DOI：

  10.1016/j.carres.2014.04.003
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-[(苯甲酰氧基)甲基]-6-氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 在 溴 、 sulfur 、 barium carbonate 作用下， 以 四氯化碳 、 硝基甲烷 为溶剂， 反应 9.0h， 生成 C-(2,3,4,6-tetra-O-benzoyl-1-hydroxy-β-D-glucopyranosyl)formamide
  参考文献：
  名称：

  一种新的可扩展制备的吡喃葡萄糖亚基-螺硫代乙内酰脲：糖原磷酸化酶的最佳抑制剂之一

  摘要：

  在硝基甲烷中，氰化汞（II）将苯溴-葡萄糖转化为过邻苯甲酰化的β-d-吡喃葡萄糖基氰化物。用溴化氢在乙酸中腈的部分水解得到过-O-苯甲酰化的C-（β-d-吡喃葡萄糖基）甲酰胺。使用溴在四氯化碳，氯仿或二氯甲烷中进行光溴化，得到相应的过-O-苯甲酰化的1-溴-1-脱氧-β-d-吡喃葡萄糖基氰化物和C-（1-溴-1-脱氧-β-d-吡喃葡萄糖基）甲酰胺 后者与硫氰酸铵在硝基甲烷中的反应得到过-O-苯甲酰化的C- 6S构型的吡喃吡喃基亚烷基-螺-硫代乙内酰脲，以及少量的O-苯甲酰化的C-（1-羟基-β-d-吡喃葡萄糖基）甲酰胺。在甲醇中用甲醇钠对螺硫代乙内酰脲进行脱苯甲酰化，得到克量的标题抑制剂。所描述的序列应适合于按比例放大，并且可以从d-葡萄糖开始以约30％的总收率制备目标化合物。

  DOI：

  10.1016/s0957-4166(00)00107-5

文献信息

• Synthesis of some O-, S- and N-glycosides of hept-2-ulopyranosonamides
  作者：Veronika Nagy、Katalin Czifrák、Attila Bényei、László Somsák

  DOI：10.1016/j.carres.2009.02.011

  日期：2009.5

  aryl glycosides were obtained with sodium phenolates; (aryl and hetaryl 2-thio-beta-D-gluco-hept-2-ulopyranoside)onamides were formed with thiophenols in the presence of K(2)CO(3) in acetone, and reactions with aniline in CH(2)Cl(2) furnished (N-phenyl beta-D-glyco-hept-2-ulopyranosylamine)onamides. Some deprotected derivatives of d-gluco configuration obtained by the Zemplen protocol showed no significant

  在Koenigs-Knorr条件下，（O-全酰化的α-D-葡萄糖和半乳糖庚基2-泛吡喃糖基溴化物）onamides得到相应的（烷基β-D-glyco-hept-2-ulopyranosylbromide）酰胺，并且类似的芳基糖苷为用酚钠制得；（芳基和杂芳基2-硫-β-D-葡萄糖-庚-2-氟吡喃糖苷）onamides在K（2）CO（3）在丙酮中与苯硫酚形成，并与苯胺在CH（2）Cl中反应（2）提供的（N-苯基β-D-糖-庚-2--2-吡喃糖胺）酰胺。通过Zemplen方案获得的一些脱保护的d-葡萄糖构型衍生物未显示出对兔肌肉糖原磷酸化酶b的显着抑制作用。
• New saccharide mimics and their use as inhibitors of angiogenesis and metastasis formation
  申请人：Deutsches Krebsforschungszentrum

  公开号：EP2474552A1

  公开（公告）日：2012-07-11

  The present invention relates to saccharide mimics which show a better biological activity at low concentrations as known saccharide mimics in inhibiting angiogenesis and inhibiting formation of metastasis by inhibiting adhesion and/or migration of human cancer cells, particularly in concentrations lower than 5 mM, and to pharmaceutical compositions comprising these saccharide mimics. The compounds of the present invention are useful as mimics of cell surface structures and, thus, for influencing cell-cell and cell-extracellular (ECM) interactions, which are controlled by bonds between protein-protein, saccharide-saccharide or saccharide-lectin on the cell-surface. Representative compounds of the present invention are for example:

  本发明涉及一种糖类模拟物，其在低浓度下表现出比已知的糖类模拟物更好的生物活性，可通过抑制人类癌细胞的粘附和/或迁移来抑制血管生成和转移的形成，特别是在低于5毫摩尔的浓度下，并涉及包含这些糖类模拟物的制药组合物。本发明的化合物可用作细胞表面结构的模拟物，从而影响由细胞表面蛋白质-蛋白质、糖类-糖类或糖类-凝集素之间的键控制的细胞-细胞和细胞-细胞外基质（ECM）相互作用。本发明的代表性化合物包括：
• Gram-scale synthesis of a glucopyranosylidene-spiro-thiohydantoin and its effect on hepatic glycogen metabolism studied in vitro and in vivo
  作者：László Somsák、Veronika Nagy、Tibor Docsa、Béla Tóth、Pál Gergely

  DOI：10.1016/s0957-4166(99)00486-3

  日期：2000.2

  A high yielding, simple synthesis is described starting from D-glucose to produce gram quantities of a glucopyranosylidene-spiro-thiohydantoin. This compound efficiently inhibited the activity of rat liver glycogen phosphorylase a; moreover, it also activated phosphorylase phosphatase which, in turn, decreased the amount of glycogen phosphorylase a. Both effects result in the inhibition of glycogen mobilization and the formation of glucose from glycogen. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] NEW SACCHARIDE MIMICS AND THEIR USE AS INHIBITORS OF ANGIOGENESIS AND METASTASIS FORMATION<br/>[FR] NOUVEAUX ANALOGUES DE GLUCIDES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'ANGIOGENÈSE ET DE LA FORMATION DE MÉTASTASES
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2012093091A2

  公开（公告）日：2012-07-12

  The present invention relates to saccharide mimics which show a better biological activity at low concentrations as known saccharide mimics in inhibiting angiogenesis and inhibiting formation of metastasis by inhibiting adhesion and/or migration of human cancer cells, particularly in concentrations lower than 5 mM, and to pharmaceutical compositions comprising these saccharide mimics. The compounds of the present invention are useful as mimics of cell surface structures and, thus, for influencing cell-cell and cell-extracellular (ECM) interactions, which are controlled by bonds between protein-protein, saccharide-saccharide or saccharide-lectin on the cell-surface.
• Anomeric spirocycles by solvent incorporation: reactions of O-peracylated (glyculopyranose and glyculopyranosyl bromide)onamide derivatives with ketones
  作者：András Páhi、Katalin Czifrák、Katalin E. Kövér、László Somsák

  DOI：10.1016/j.carres.2014.04.003

  日期：2015.2

  Reactions of O-peracetylated (alpha-D-galacto-heptulopyranosyl bromide)onamide and O-perbenzoylated (alpha-D-gluco-heptulopyranosyl bromide)onamide with ketones in the presence of silver(I) salt promoters gave the corresponding O-peracylated 1',5'-anhydro-D-glycitol-spiro-[1',5]-4-imino-2,2-disubstituted-1,3-dioxolanes. The D-galacto configured starting compounds furnished both spiro epimers, while

  在银（I）盐促进剂存在下，O-全乙酰化（α-D-半乳糖-庚基吡喃糖基溴）酰胺和O-过苯甲酰化（α-D-葡萄糖-庚基吡喃糖基溴）酮与酮的反应得到相应的O-过酰基化的1 '，5'-脱水-D-糖醇-螺-[1'，5] -4-亚氨基-2，2-二取代-1，3-二氧戊环。D-半乳糖构型的起始化合物提供了两个螺旋差向异构体，而D-葡萄糖相应物仅产生构型上的倒位产物。在酸性条件下，O-过苯甲酰化的α-D-葡萄糖-庚基吡咯烷酰胺和酮产生受保护的1'，5'-脱水-D-葡萄糖醇-螺-[1'，5] -2,2-二取代-恶唑烷-4-通过Zemplen方案O-去苯甲酰化的那些 这些化合物对兔肌肉糖原磷酸酶b没有抑制作用。