[2'-hydroxy-4-methoxy-5'-(2-oxo-ethyl)-1,1'-biphenyl-3-yl]-acetaldehyde | 1315334-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2'-hydroxy-4-methoxy-5'-(2-oxo-ethyl)-1,1'-biphenyl-3-yl]-acetaldehyde
• 英文别名: 2-[4-Hydroxy-3-[4-methoxy-3-(2-oxoethyl)phenyl]phenyl]acetaldehyde
• CAS: 1315334-12-3
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: IEFLGLDYFHYJRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2'-hydroxy-4-methoxy-5'-(2-oxo-ethyl)-1,1'-biphenyl-3-yl]-acetaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 以22%的产率得到4'-methoxy-3',5-di-(2-hydroxyethyl)-biphenyl-2-ol
  参考文献：
  名称：

  Modulation of GABA_A-Receptors by Honokiol and Derivatives: Subtype Selectivity and Structure–Activity Relationship

  摘要：

  A series of 31 analogues of the neolignan honokiol (a major constituent of Magnolia officinalis) was synthesized, and their effects on GABA(A) receptors expressed in Xenopus oocytes were investigated. Honokiol enhanced chloride currents (I-GABA) through GABA(A) receptors of seven different subunit compositions with EC50 values ranging from 23.4 mu M (alpha(5)beta(2)) to 59.6 mu M (alpha(1)beta(3)). Honolciol was most efficient on alpha(3)beta(2) (maximal IGABA enhancement 2386%) > alpha(2)beta(2) (1130%) > alpha(1)beta(2) (1034%) > alpha(1)beta(1) (260%)). On alpha(1)beta(2)-receptors, N-substituted compounds were most active with 3-acetylamino-4'-O-methylhonolciol (31), enhancing I-GABA by 2601% (EC50 (alpha(1)beta(2)) = 3.8 mu M). Pharmacophore modeling gave a model with an overall classification accuracy of 91% showing three hydrophobic regions, one acceptor and one donor region. Unlike honokiol, 31 was most efficient on alpha(2)beta(2)- (5204%) > alpha(3)beta(2)- (3671%) > alpha(1)beta(2)-receptors (2601%), suggesting a role of the acetamido group in subunit-dependent receptor modulation.

  DOI：

  10.1021/jm200186n
• 作为产物：
  描述：

  4'-甲氧基-3',5-二-2-丙烯基-(1,1'-联苯)-2-醇 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.62h， 生成 [2'-hydroxy-4-methoxy-5'-(2-oxo-ethyl)-1,1'-biphenyl-3-yl]-acetaldehyde
  参考文献：
  名称：

  Modulation of GABA_A-Receptors by Honokiol and Derivatives: Subtype Selectivity and Structure–Activity Relationship

  摘要：

  A series of 31 analogues of the neolignan honokiol (a major constituent of Magnolia officinalis) was synthesized, and their effects on GABA(A) receptors expressed in Xenopus oocytes were investigated. Honokiol enhanced chloride currents (I-GABA) through GABA(A) receptors of seven different subunit compositions with EC50 values ranging from 23.4 mu M (alpha(5)beta(2)) to 59.6 mu M (alpha(1)beta(3)). Honolciol was most efficient on alpha(3)beta(2) (maximal IGABA enhancement 2386%) > alpha(2)beta(2) (1130%) > alpha(1)beta(2) (1034%) > alpha(1)beta(1) (260%)). On alpha(1)beta(2)-receptors, N-substituted compounds were most active with 3-acetylamino-4'-O-methylhonolciol (31), enhancing I-GABA by 2601% (EC50 (alpha(1)beta(2)) = 3.8 mu M). Pharmacophore modeling gave a model with an overall classification accuracy of 91% showing three hydrophobic regions, one acceptor and one donor region. Unlike honokiol, 31 was most efficient on alpha(2)beta(2)- (5204%) > alpha(3)beta(2)- (3671%) > alpha(1)beta(2)-receptors (2601%), suggesting a role of the acetamido group in subunit-dependent receptor modulation.

  DOI：

  10.1021/jm200186n