2-acetamido-3,4,6-tri-O-acetyl-1-O-butanoyl-2-deoxy-α,β-D-mannopyranose | 1108149-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-1-O-butanoyl-2-deoxy-α,β-D-mannopyranose
• 英文别名: 1-O-butanoyl-3,4,6-O-Ac3ManNAc；[(3S,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl] butanoate
• CAS: 1108149-62-7
• 化学式: C₁₈H₂₇NO₁₀
• 分子量: 417.413
• InChiKey: SDHLHFVBDOEAQI-GAMQSXCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose 在 4-二甲氨基吡啶 吡啶 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-1-O-butanoyl-2-deoxy-α,β-D-mannopyranose
  参考文献：
  名称：

  [EN] HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS
  [FR] MONOSACCHARIDES HYBRIDES DÉRIVATISÉS AVEC HYDROXYLE /SCFA (ACIDES GRAS À CHAÎNE COURTE), PROCÉDÉS DE SYNTHÈSE, ET PROCÉDÉS DE TRAITEMENT DE TROUBLES

  摘要：

  本文描述了脂肪酸碳水化合物及其衍生物，以及利用这些化合物及其组合物治疗或预防疾病和疾病症状的方法。

  公开号：

  WO2009020641A1

文献信息

• Hexosamine Template. A Platform for Modulating Gene Expression and for Sugar-Based Drug Discovery
  作者：Noha Elmouelhi、Udayanath Aich、Venkata D. P. Paruchuri、M. Adam Meledeo、Christopher T. Campbell、Jean J. Wang、Raja Srinivas、Hargun S. Khanna、Kevin J. Yarema

  DOI：10.1021/jm801661m

  日期：2009.4.23

  This study investigates the breadth of cellular responses engendered by short chain fatty acid (SCFA)-hexosamine hybrid molecules, a class of compounds long used in "metabolic glycoengineering" that are now emerging as drug candidates. First, a "mix and match" strategy showed that different SCFA (n-butyrate and acetate) appended to the same core sugar altered biological activity, complementing previous results [Campbell et al. J. Med. Chem. 2008, 51, 8135-8147] where a single type of SCFA elicited distinct responses. Microarray profiling then compared transcriptional responses engendered by regioisomerically modified ManNAc, GlcNAc, and GalNAc analogues in MDA-MB-231 cells. These data, which were validated by qRT-PCR or Western analysis for IDI, TP53, HPSE, NQO1, EGR1, and VEGFA, showed a two-pronged response where a core set of genes was coordinately regulated by all analogues while each analogue simultaneously uniquely regulated a larger number of genes. Finally, AutoDock modeling supported a mechanism where the analogues directly interact with elements of the NF-kappa B pathway. Together, these results establish the SCFA-hexosamine template as a versatile platform for modulating biological activity and developing new therapeutics.
• HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS
  申请人：Yarema Kevin J.

  公开号：US20110206734A1

  公开（公告）日：2011-08-25

  Described herein are fatty acid carbohydrate-hydroxyl-hybrid compounds and derivatives thereof, and methods of treating or preventing disease and disease symptoms using the compounds and compositions thereof.
• US8916544B2
  申请人：——

  公开号：US8916544B2

  公开（公告）日：2014-12-23
• US9067960B2
  申请人：——

  公开号：US9067960B2

  公开（公告）日：2015-06-30
• [EN] HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS<br/>[FR] MONOSACCHARIDES HYBRIDES DÉRIVATISÉS AVEC HYDROXYLE /SCFA (ACIDES GRAS À CHAÎNE COURTE), PROCÉDÉS DE SYNTHÈSE, ET PROCÉDÉS DE TRAITEMENT DE TROUBLES
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2009020641A1

  公开（公告）日：2009-02-12

  Described herein are fatty acid carbohydrate-hydroxyl-hybrid compounds and derivatives thereof, and methods of treating or preventing disease and disease symptoms using the compounds and compositions thereof.

  本文描述了脂肪酸碳水化合物及其衍生物，以及利用这些化合物及其组合物治疗或预防疾病和疾病症状的方法。