1-{4-(4-hydroxyphenyl)butyl}-L-arabinoiminofuranose | 1618658-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-{4-(4-hydroxyphenyl)butyl}-L-arabinoiminofuranose
• 英文别名: (2S,3S,4S,5S)-2-(hydroxymethyl)-5-[4-(4-hydroxyphenyl)butyl]pyrrolidine-3,4-diol
• CAS: 1618658-06-2
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: FSTMLQIUWBDDRD-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(4-hydroxyphenyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以61%的产率得到1-{4-(4-hydroxyphenyl)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.