(2-benzyl-phenoxy)acetaldehyde | 132481-29-9

• 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-benzyl-phenoxy)acetaldehyde
• 英文别名: 2-(2-Benzylphenoxy)acetaldehyde
• CAS: 132481-29-9
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: QDZKYNZYJDCGKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((2,6-二甲氧基苯基)氧基)乙胺 、 (2-benzyl-phenoxy)acetaldehyde 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以56%的产率得到2-(2-benzylphenoxy)-N-[2-(2,6-dimethoxyphenoxy)ethyl]ethanamine
  参考文献：
  名称：

  Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 7. Selectivity of 4-Phenylchroman Analogues for α₁−Adrenoreceptor Subtypes

  摘要：

  WB4101 (1)-related compounds 5-10 were synthesized, and their biological profile at alpha(1)-adrenoreceptor (AR) subtypes and 5-HT1A serotoninergic receptors was assessed by binding assays in Chinese hamster ovary and HeLa cell membranes expressing the human cloned receptors. Moreover, their receptor selectivity was further determined in functional experiments in isolated rat prostate (alpha(1A)), vas deferens (alpha(1A)), aorta (alpha(1D)), and spleen (alpha(1B)). In functional assays, compound 5 was the most potent at alpha(1D)-ARs with a reversed selectivity profile (alpha(1D) > alpha(1A) > alpha(1B)) relative to both prototype 1 and phendioxan (2) (alpha(1A) > alpha(1D) > alpha(1D)), whereas compound 8, bearing a carbonyl moiety at position 1, was the most potent at alpha(1)-ARs with a selectivity profile similar to that of prototypes. The least potent of the series was the trans isomer 6, suggesting that optimum alpha(1)-AR blocking activity in this series is associated with a cis relationship between the 2-side chain and the 4-phenyl ring rather than a trans relationship as previously observed for the 2-side chain and the 3-phenyl ring in 2 and related compounds. Binding affinity results were not in complete agreement with the selectivity profiles deriving from functional experiments. Although a firm explanation was not available, neutral and negative antagonism and receptor dimerization were considered as two possibilities to account for the difference between binding and functional affinities. Finally, compound 5 was selected for a modeling study in comparison with 1, mephendioxan (3), and open phendioxan (4) to achieve information on the physicochemical interactions that account for its high affinity toward alpha(1d/D)-ARs.

  DOI：

  10.1021/jm011066n
• 作为产物：
  描述：

  苯甲基苯酚 在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 11.0h， 生成 (2-benzyl-phenoxy)acetaldehyde
  参考文献：
  名称：

  Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 7. Selectivity of 4-Phenylchroman Analogues for α₁−Adrenoreceptor Subtypes

  摘要：

  WB4101 (1)-related compounds 5-10 were synthesized, and their biological profile at alpha(1)-adrenoreceptor (AR) subtypes and 5-HT1A serotoninergic receptors was assessed by binding assays in Chinese hamster ovary and HeLa cell membranes expressing the human cloned receptors. Moreover, their receptor selectivity was further determined in functional experiments in isolated rat prostate (alpha(1A)), vas deferens (alpha(1A)), aorta (alpha(1D)), and spleen (alpha(1B)). In functional assays, compound 5 was the most potent at alpha(1D)-ARs with a reversed selectivity profile (alpha(1D) > alpha(1A) > alpha(1B)) relative to both prototype 1 and phendioxan (2) (alpha(1A) > alpha(1D) > alpha(1D)), whereas compound 8, bearing a carbonyl moiety at position 1, was the most potent at alpha(1)-ARs with a selectivity profile similar to that of prototypes. The least potent of the series was the trans isomer 6, suggesting that optimum alpha(1)-AR blocking activity in this series is associated with a cis relationship between the 2-side chain and the 4-phenyl ring rather than a trans relationship as previously observed for the 2-side chain and the 3-phenyl ring in 2 and related compounds. Binding affinity results were not in complete agreement with the selectivity profiles deriving from functional experiments. Although a firm explanation was not available, neutral and negative antagonism and receptor dimerization were considered as two possibilities to account for the difference between binding and functional affinities. Finally, compound 5 was selected for a modeling study in comparison with 1, mephendioxan (3), and open phendioxan (4) to achieve information on the physicochemical interactions that account for its high affinity toward alpha(1d/D)-ARs.

  DOI：

  10.1021/jm011066n

文献信息

• [EN] DHODH INHIBITORS AND THEIR USE AS ANTIVIRAL AGENTS<br/>[FR] INHIBITEURS DE DHODH ET LEUR UTILISATION EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV HAMBURG

  公开号：WO2020225330A1

  公开（公告）日：2020-11-12

  The present invention relates to a compound, or a dimer or a pharmaceutically acceptable salt or solvate of said compound or dimer, for use in a method for the treatment of a disease, disorder or condition caused by an RNA virus, said compound having the general structure shown in Formula (I).

  本发明涉及一种化合物，或者该化合物或二聚体的药学上可接受的盐或溶剂，用于治疗由RNA病毒引起的疾病、紊乱或症状的方法，所述化合物具有如公式(I)所示的一般结构。
• Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 7. Selectivity of 4-Phenylchroman Analogues for α₁−Adrenoreceptor Subtypes
  作者：Wilma Quaglia、Maria Pigini、Alessandro Piergentili、Mario Giannella、Francesco Gentili、Gabriella Marucci、Antonio Carrieri、Angelo Carotti、Elena Poggesi、Amedeo Leonardi、Carlo Melchiorre

  DOI：10.1021/jm011066n

  日期：2002.4.1

  WB4101 (1)-related compounds 5-10 were synthesized, and their biological profile at alpha(1)-adrenoreceptor (AR) subtypes and 5-HT1A serotoninergic receptors was assessed by binding assays in Chinese hamster ovary and HeLa cell membranes expressing the human cloned receptors. Moreover, their receptor selectivity was further determined in functional experiments in isolated rat prostate (alpha(1A)), vas deferens (alpha(1A)), aorta (alpha(1D)), and spleen (alpha(1B)). In functional assays, compound 5 was the most potent at alpha(1D)-ARs with a reversed selectivity profile (alpha(1D) > alpha(1A) > alpha(1B)) relative to both prototype 1 and phendioxan (2) (alpha(1A) > alpha(1D) > alpha(1D)), whereas compound 8, bearing a carbonyl moiety at position 1, was the most potent at alpha(1)-ARs with a selectivity profile similar to that of prototypes. The least potent of the series was the trans isomer 6, suggesting that optimum alpha(1)-AR blocking activity in this series is associated with a cis relationship between the 2-side chain and the 4-phenyl ring rather than a trans relationship as previously observed for the 2-side chain and the 3-phenyl ring in 2 and related compounds. Binding affinity results were not in complete agreement with the selectivity profiles deriving from functional experiments. Although a firm explanation was not available, neutral and negative antagonism and receptor dimerization were considered as two possibilities to account for the difference between binding and functional affinities. Finally, compound 5 was selected for a modeling study in comparison with 1, mephendioxan (3), and open phendioxan (4) to achieve information on the physicochemical interactions that account for its high affinity toward alpha(1d/D)-ARs.