(2R,3R)-cis-4'-methoxyflavan-3-ol | 1196870-17-3

• 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: (2R,3R)-cis-4'-methoxyflavan-3-ol
• 英文别名: (2R,3R)-2-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-3-ol
• CAS: 1196870-17-3
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: XPXNUSNIJPFVIP-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-cis-4'-methoxyflavan-3-ol 、 乙酸酐 在 吡啶 作用下， 以99%的产率得到(2R,3R)-cis-3-acetoxy-4'-methoxyflavan
  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：

  (1R,2R)-1-(4-methoxyphenyl)-3-[2-(methoxymethoxy)phenyl]propane-1,2-diol 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 (2S,3R)-trans-4'-methoxyflavan-3-ol 、 (2R,3R)-cis-4'-methoxyflavan-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

文献信息

• BIRD, T. G. C.;BROWN, B. R.;STUART, I. A.;TYRRELL, A. W. R., CHEM. SOC. PERKIN TRANS., 1983, N 7, 1831-1846
  作者：BIRD, T. G. C.、BROWN, B. R.、STUART, I. A.、TYRRELL, A. W. R.

  DOI：——

  日期：——
• Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors
  作者：Kenneth N. Mewett、Sebastian P. Fernandez、Anmol K. Pasricha、Alice Pong、Steven O. Devenish、David E. Hibbs、Mary Chebib、Graham A.R. Johnston、Jane R. Hanrahan

  DOI：10.1016/j.bmc.2009.08.062

  日期：2009.10

  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.