1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose | 179913-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose
• 英文别名: [(4S,5R,6S)-5-acetyloxy-4-azido-6-methyloxan-2-yl] acetate
• CAS: 179913-39-4
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: JOLFYRYOQBSGFK-FIEGVUJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  110.59
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose 在 吡啶 、 lithium hydroxide 、 2,6-二叔丁基-4-甲基吡啶 、 18-冠醚-6 、 三氟甲磺酸酐 、 4 A molecular sieve 、 三氟化硼乙醚 、 mercury(II) trifluoroacetate 、 sodium hydride 、 potassium carbonate 、 氟化氢吡啶 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.74h， 生成 methyl [[[[(3-azido-2,3-dideoxy-4-O-methyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-L-fucopyranoside
  参考文献：
  名称：

  Design of an Oligosaccharide Scaffold That Binds in the Minor Groove of DNA

  摘要：

  Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. In this paper, the use of oligosaccharides as scaffolds for the design of peptidomimetics is addressed. A functionalized oligosaccharide modeled after a basic region peptide helix has been designed and synthesized. This oligosaccharide binds to duplex DNA with micromolar affinity. The mode of binding has been established by 2D NMR, and shows that the oligosaccharide binds DNA in the minor groove with one surface of the oligosaccharide contacting the floor of the DNA.

  DOI：

  10.1021/ja992513f
• 作为产物：
  描述：

  乙酸酐 、 2-deoxy-3-azido-4-O-acetyl-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 0.33h， 生成 1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose
  参考文献：
  名称：

  Design of an Oligosaccharide Scaffold That Binds in the Minor Groove of DNA

  摘要：

  Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. In this paper, the use of oligosaccharides as scaffolds for the design of peptidomimetics is addressed. A functionalized oligosaccharide modeled after a basic region peptide helix has been designed and synthesized. This oligosaccharide binds to duplex DNA with micromolar affinity. The mode of binding has been established by 2D NMR, and shows that the oligosaccharide binds DNA in the minor groove with one surface of the oligosaccharide contacting the floor of the DNA.

  DOI：

  10.1021/ja992513f

文献信息

• WO2006/124720
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ALOE-EMODIN DERIVATIVES AND USE THEREOF FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS D'ALOÉ-ÉMODINE ET LEUR UTILISATION POUR LE TRAITEMENT DU CANCER
  申请人：UNIV RAMOT

  公开号：WO2011089602A3

  公开（公告）日：2011-12-29
• Targeting Anthracycline-Resistant Tumor Cells with Synthetic Aloe-Emodin Glycosides
  作者：Elinor Breiner-Goldstein、Zoharia Evron、Michael Frenkel、Keren Cohen、Keren Nir Meiron、Dan Peer、Yael Roichman、Eliezer Flescher、Micha Fridman

  DOI：10.1021/ml2001104

  日期：2011.7.14

  The cytotoxic activity of aloe-emodin (AE), a natural anthranoid that readily permeates anthracycline-resistant tumor cells, was improved by the attachment of an amino-sugar unit to its anthraquinone core. The new class of AE glycosides (AEGs) showed a significant improvement in cytotoxicity-up to more than 2 orders of magnitude greater than those of AE and the clinically used anthracycline doxorubicin (DOX)-against several cancer cell lines with different levels of DOX resistance. Incubation with the synthetic AEGs induced cell death in less than one cell cycle, indicating that these compounds do not directly target the cell division mechanism. Confocal microscopy provided evidence that unlike DOX, AEGs accumulated in anthracycline-resistant tumor cells in which resistance is conferred by P-glycoprotein efflux pumps. The results of this study demonstrate that AEGs may serve as a promising scaffold for the development of cytotoxic agents capable of overcoming anthracycline resistance in tumor cells.
• ——
  作者：Sofia Mitaku、Alexios‐Léandros Skaltsounis、François Tillequin、Michel Koch、Yves Rolland、Alain Pierré、Ghanem Atassi

  DOI：10.1023/a:1016073700344

  日期：——

  Purpose. Combination of the acronycine pharmacophore with various sugar units appeared of interest, since numerous anticancer agents possess a sugar moiety, which strongly influence both their bioavailability and their selective toxicity towards tumor cells.Methods. A series of 2-hydroxy-1,2-dihydroacronycine glycosides were synthetized, by condensation of the racemic aglycone with appropriate glycoside donors. Their effect on the inhibition of L1210 cell proliferation were evaluated.Results. Compounds 6a, 6b, 11a, 11b, and 12a, 12b, including a halogenated sugar moiety displayed activities of the same order of magnitude as acronycine itself. Compounds 7a, 7b, and Sa, 8b, bearing a 2,3,6-trideoxy-3-azido-L-lyxo- and L-arabino-hexopyranose unit respectively, were significantly more potent than acronycine in inhibiting cell proliferation.Conclusions. The activity of 2-hydroxy-1,2-dihydroacronycine glycosides seems to be related to the Lipophilicity of the sugar unit.
• The Structure of Anthracycline Derivatives Determines Their Subcellular Localization and Cytotoxic Activity
  作者：Pazit Shaul、Michael Frenkel、Elinor Briner Goldstein、Leonid Mittelman、Assaf Grunwald、Yuval Ebenstein、Ilan Tsarfaty、Micha Fridman

  DOI：10.1021/ml3002852

  日期：2013.3.14

  The cytotoxic activities and subcellular localizations of clinically used and synthetic analogues of the anthracycline family of chemotherapeutic agents were studied. The structures of the anthracycline derivatives affected their cytotoxicity and the time required for these compounds to exert cytotoxic effects on tumor cells. Fluorescent DNA intercalator displacement experiments demonstrated that there was no correlation between the DNA intercalation properties and the cytotoxicity of the studied anthracycline derivatives. Confocal microscopy experiments indicated that structural differences led to differences in subcellular localization. All studied anthracycline derivatives were observed in lysosomes, suggesting that this organelle, which is involved in several processes leading to malignancy, may contain previously unidentified molecular targets for these antitumor agents.