(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(4-hydroxyphenyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one | 1618658-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(4-hydroxyphenyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
• CAS: 1618658-02-8
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: BDOCSSXGNHRTPZ-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.23
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (3-(4-acetoxyphenyl)propyl)zinc(II) bromide 在 Oxone 、 bis(1,5-cyclooctadiene)nickel (0) 、 乙二胺四乙酸 、 1,1,1-三氟丙酮 、 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 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 水 、 乙腈 为溶剂， 反应 96.0h， 生成 (5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(4-hydroxyphenyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
  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