cis-(2S,3S)-4'-(phenylmethoxy)flavan-3-ol | 1196870-51-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: cis-(2S,3S)-4'-(phenylmethoxy)flavan-3-ol
• CAS: 1196870-51-5
• 化学式: C₂₂H₂₀O₃
• 分子量: 332.399
• InChiKey: COOIHAJMTFVXPR-UNMCSNQZSA-N

反应信息

• 作为反应物：
  描述：

  cis-(2S,3S)-4'-(phenylmethoxy)flavan-3-ol 、 乙酸酐 在 吡啶 作用下， 以100%的产率得到cis-(2S,3S)-3-acetoxy-4'-(phenylmethoxy)flavan
  参考文献：
  名称：

  Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors

  摘要：

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.062
• 作为产物：
  描述：

  (1S,2S)-1-[4-(phenylmethoxy)phenyl]-3-[2-(methoxymethoxy)phenyl]propane-1,2-diol 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 cis-(2S,3S)-4'-(phenylmethoxy)flavan-3-ol 、 (2R,3S)-2-(4-(benzyloxy)phenyl)chroman-3-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors

  摘要：

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.062