(E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-4-(3',4'-dimethoxyphenyl)but-3-en-2-one | 1164131-68-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-4-(3',4'-dimethoxyphenyl)but-3-en-2-one
• CAS: 1164131-68-3
• 化学式: C₂₃H₂₈O₁₀
• 分子量: 464.469
• InChiKey: HNIYOZPWOFRSCX-NCDRUTMPSA-N

反应信息

• 作为反应物：
  描述：

  (E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-4-(3',4'-dimethoxyphenyl)but-3-en-2-one 在 甲醇 、 sodium methylate 作用下， 以82%的产率得到(E)-1-(β-D-xylopyranosyl)-4-(3',4'-dimethoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity

  摘要：

  A simple synthesis of phenyl butenoyl C-glycosides has been achieved by Aldol condensation of peracetylated glycosyl acetones with aromatic aldehydes followed by deacetylation with methanolic NaOMe. The selected butenoyl C-glycosides on conjugate addition of diethyl malonate resulted in polyfunctional alkanonyl glycosides in good yields. The butenoyl C- and alkanoyl C- glycosides were evaluated for their alpha-glucosidase, glucose-6-phosphatse and glycogen phosphorylase enzyme inhibitory activities in vitro. Three of the synthesized (3, 5 and 9) showed potent enzyme inhibitory activities as compared to standard drugs. Compounds 3, 5 and 9 were evaluated in vivo too displaying significant activity as compared to standard drugs acarbose and metformin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.136