1-{4-(4-fluorophenyl)butyl}-L-arabinoiminofuranose | 1618658-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{4-(4-fluorophenyl)butyl}-L-arabinoiminofuranose
• 英文别名: (2S,3S,4S,5S)-2-[4-(4-fluorophenyl)butyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 1618658-07-3
• 化学式: C₁₅H₂₂FNO₃
• 分子量: 283.343
• InChiKey: NCIBNAATYWGBOH-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3-溴丙基)-4-氟苯 在 Oxone 、 bis(1,5-cyclooctadiene)nickel (0) 、 乙二胺四乙酸 、 1,1,1-三氟丙酮 、 碘 、 碳酸氢钠 、 (S,S)-2,6-双(4-异丙基-2-恶唑啉-2-基)吡啶 、 三氟乙酸 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基乙酰胺 、 水 、 乙腈 为溶剂， 反应 101.0h， 生成 1-{4-(4-fluorophenyl)butyl}-L-arabinoiminofuranose
  参考文献：
  名称：

  Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l-arabinoiminofuranoses, a new class of α-glucosidase inhibitors

  摘要：

  A series of alpha-1-C-4'-arylbutyl-L-arabinoiminofuranoses 3 with functional groups attached to the phenyl ring, which are potential alpha-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives 3a-e showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative 3e showed good inhibition activities against intestinal isomaltase and sucrase as compared to those of 1 and commercial drugs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.001

文献信息

• Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l-arabinoiminofuranoses, a new class of α-glucosidase inhibitors
  作者：Yoshihiro Natori、Toshihiro Sakuma、Yuichi Yoshimura、Kyoko Kinami、Yuki Hirokami、Kasumi Sato、Isao Adachi、Atsushi Kato、Hiroki Takahata

  DOI：10.1016/j.bmcl.2014.06.001

  日期：2014.8

  A series of alpha-1-C-4'-arylbutyl-L-arabinoiminofuranoses 3 with functional groups attached to the phenyl ring, which are potential alpha-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives 3a-e showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative 3e showed good inhibition activities against intestinal isomaltase and sucrase as compared to those of 1 and commercial drugs. (C) 2014 Elsevier Ltd. All rights reserved.