1,2-O-Isopropylidene-3-C-phenyl-5-(4-(3-chloropropyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose | 1357178-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-Isopropylidene-3-C-phenyl-5-(4-(3-chloropropyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-[[4-(3-chloropropyl)triazol-1-yl]methyl]-2,2-dimethyl-6-phenyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 1357178-72-3
• 化学式: C₁₉H₂₄ClN₃O₄
• 分子量: 393.87
• InChiKey: FIZHIFKVRPJTQX-SFNKJDCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  葡萄糖 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 phosphomolybdic acid 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 草酰氯 、 碘 、 silica gel 、 二甲基亚砜 、 sodium ascorbate 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 67.5h， 生成 1,2-O-Isopropylidene-3-C-phenyl-5-(4-(3-chloropropyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases

  摘要：

  Ten new 1,2,3-triazole glycoconjugates were synthesized from D-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme a-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3-phenyl-5-(4-phenyl- 1H-1,2,3-triazole-1-yl)-alpha-D-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.026

文献信息

• Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases
  作者：David R. da Rocha、Wilson C. Santos、Emerson S. Lima、Vitor F. Ferreira

  DOI：10.1016/j.carres.2011.12.026

  日期：2012.3

  Ten new 1,2,3-triazole glycoconjugates were synthesized from D-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme a-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3-phenyl-5-(4-phenyl- 1H-1,2,3-triazole-1-yl)-alpha-D-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed. (C) 2012 Elsevier Ltd. All rights reserved.