1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranose-1-yl)-4-(4-methyl-2H-chromen-2-one-7-yloxymethyl)-1,2,3-1H-triazole | 1263036-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranose-1-yl)-4-(4-methyl-2H-chromen-2-one-7-yloxymethyl)-1,2,3-1H-triazole
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-[(4-methyl-2-oxochromen-7-yl)oxymethyl]triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1263036-28-7
• 化学式: C₂₇H₂₉N₃O₁₂
• 分子量: 587.54
• InChiKey: POHVJUYITCGEGL-UIKHAHSZSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  718.3±70.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranose-1-yl)-4-(4-methyl-2H-chromen-2-one-7-yloxymethyl)-1,2,3-1H-triazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以88%的产率得到7-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methoxy]-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors

  摘要：

  An efficient synthesis of novel 1,2,3-1H-triazolyl glycohybrids with two or more than two sugar units or a chromenone moiety via copper-catalysed azide-alkyne cycloaddition (CuAAC), a 1,3-dipolar cycloaddition of glycosyl azides to 2,3-unsaturated alkynyl glycosides or propargyloxy coumarins is described. The synthesised glycohybrids were screened for their a-glucosidase, glycogen phosphorylase and glucose-6-phosphatase inhibitory activities. A few of the glycohybrids showed promising inhibitory activities against these enzymes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.10.017
• 作为产物：
  描述：

  吉帕孟 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 sonochemically Fe₃O₄ and CuO-decorated graphene oxide magnetic nanocomposite 作用下， 以 水 为溶剂， 反应 1.0h， 以95%的产率得到1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranose-1-yl)-4-(4-methyl-2H-chromen-2-one-7-yloxymethyl)-1,2,3-1H-triazole
  参考文献：
  名称：

  Sonochemical Decoration of Graphene Oxide with Magnetic Fe3O4@CuO Nanocomposite for Efficient Click Synthesis of Coumarin-Sugar Based Bioconjugates and Their Cytotoxic Activity

  摘要：

  A magnetic nanocomposite of GO-Fe3O4@CuO was fabricated via a simple sonochemical technique and successfully utilized for the ultrasound promoted synthesis of regioselective 1,4-disubstituted mono/bis/tris-1,2,3-triazoles (3a-k). This catalyst could be separated conveniently from the reaction mixture using an external magnet and reused up to eight consecutive runs without noticeable drop in the desired product yield. Other noteworthy features of this green protocol are negligible metal leaching from the support during reaction, high yield in lesser time, aqueous media and good results with gram scale synthesis. Representative compounds were also screened for their cytotoxic activity against PC-12 cell line using standard MTT assay and flow cytometry. Trifluoromethyl group containing triazole derivative (3f) displayed cytotoxic activity (IC50 8.3 mu g/mL) comparable to the standard drug cisplatin (IC50 5.8 mu g/mL).[GRAPHICS].

  DOI：

  10.1007/s10562-019-02982-6