Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a)-O-prop-2-ynyl | 943859-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a)-O-prop-2-ynyl
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-prop-2-ynoxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 943859-76-5
• 化学式: C₂₉H₃₈O₁₈
• 分子量: 674.61
• InChiKey: NXVPJXKDYQZVDU-NFBYRGHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a)-O-prop-2-ynyl 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以98 %的产率得到
  参考文献：
  名称：

  New Selective Inhibitors of α‐Glucosidase for the Treatment of Type 2 Diabetes Mellitus

  摘要：

  Type 2 diabetes mellitus is a metabolic dreadful disease caused by an uncontrolled glucose level in the bloodstream, particularly high after a meal. Inhibitors of glucosidases, involved in the digestion of carbohydrates, can regulate this post‐prandial increase in glucose concentration. The traditional drugs act as competitive inhibitors of both pancreatic α‐amylase and α‐glucosidases and this unselective inhibition is behind severe gastrointestinal side effects related to the concomitant inhibition of α‐amylase. We described herein some perglycosylated cyclodextrins as efficient and selective inhibitors of α‐glucosidase with low micromolar IC50 (3.64‐7.98 μM) compared to the acarbose (IC50 212 μM), clinically used for patients suffering from type 2 diabetes. On the other hand, they do not inhibit α‐amylase (IC50>500 μM). Structure/activity relationship rationalization suggests multiple interactions between the described inhibitors and α‐glucosidase, which support the existence of both active site and allosteric interactions.

  DOI：

  10.1002/hlca.202300222
• 作为产物：
  描述：

  D-(+)-纤维二糖 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a)-O-prop-2-ynyl
  参考文献：
  名称：

  单击化学：取代类固醇，皂角苷和洋地黄类似物的杂环的有效合成。

  摘要：

  铜催化的叠氮化物-炔烃环加成反应（CuAAC）已用于高产，高产的含1,2,3-三唑类固醇的构建。炔丙基糖苷和甾类叠氮化物作为反应伴侣的组合允许合成一类特权的天然产物类似物。该方案的多功能性使该化学成为合成目标分子的有用的有吸引力的方法。 点击化学-1,2,3-三唑-糖-类固醇-皂苷-洋地黄

  DOI：

  10.1055/s-0031-1289606

文献信息

• Click reaction synthesis of carbohydrate derivatives from ristocetin aglycon with antibacterial and antiviral activity
  作者：Gábor Pintér、Ilona Bereczki、Gyula Batta、Réka Ötvös、Ferenc Sztaricskai、Erzsébet Rőth、Eszter Ostorházi、Ferenc Rozgonyi、Lieve Naesens、Mariann Szarvas、Zoltán Boda、Pál Herczegh

  DOI：10.1016/j.bmcl.2010.03.080

  日期：2010.5

  New sugar derivatives of ristocetin were prepared by copper-catalyzed 1,3-dipolar cycloaddition reaction using azido-ristocetin aglycon and various propargyl glycosides. Some of them were found to be active against Gram-positive bacteria and showed favorable antiviral activity against the H1N1 subtype of influenza A virus. (C) 2010 Elsevier Ltd. All rights reserved.