N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(4-hydroxy-3-nitrophenyl)acetamide | 185104-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(4-hydroxy-3-nitrophenyl)acetamide
• CAS: 185104-75-0
• 化学式: C₃₀H₂₈N₂O₆
• 分子量: 512.562
• InChiKey: UIMRYOZARGAAPV-UHFFFAOYSA-N

物化性质

• 沸点：
  746.2±60.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(4-hydroxy-3-nitrophenyl)acetamide 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.5h， 生成 4-[[6,7-Bis(phenylmethoxy)-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-2-nitrophenol
  参考文献：
  名称：

  Synthesis and Evaluation of Trimetoquinol Derivatives:  Novel Thromboxane A₂/Prostaglandin H₂ Antagonists with Diminished β-Adrenergic Agonist Activity

  摘要：

  Trimetoquinol (TMQ, 1) is a unique catecholamine with a strong stereodependence for agonism at beta-adrenergic (S much greater than R) and antagonism at thromboxane A(2)/prostaglandin H-2 (TP; R much greater than S) receptors. Our laboratory has reported the effects of N-alkylation and modification of the trisubstituted benzyl group in these receptor systems. For iodinated derivative 5, maintaining potency in TP receptor systems (112%) was coupled with maintaining limited potency in beta-adrenergic receptor systems (34% for beta(1) and 47% for beta(2)) In this study, several diverse TMQ derivatives were prepared to probe for binding interactions specific to a particular receptor system. Planar amidine 2, which was designed to explore the importance of TMQ's chiral center, showed a dramatic loss of potency (<1%) in each receptor system. Likewise, the homologation of a previously described N-benzyl derivative (3) to the N-phenylethyl derivative 4 also showed reduced potency (<3%) in both receptor systems. However, modification of the trimethoxybenzyl group of TMQ to a 4-hydroxy-3-nitrobenzyl group (7) provided a unique lead for TMQ derivatives with significant potency in TP receptor systems (91%) and reduced potency in beta-adrenergic receptor systems (4% for beta(1) and 19% for beta(2)).

  DOI：

  10.1021/jm950896w
• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 、 3,4-di(benzyloxy)phenethylamine 以 甲苯 为溶剂， 反应 72.0h， 生成 N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(4-hydroxy-3-nitrophenyl)acetamide
  参考文献：
  名称：

  Synthesis and Evaluation of Trimetoquinol Derivatives:  Novel Thromboxane A₂/Prostaglandin H₂ Antagonists with Diminished β-Adrenergic Agonist Activity

  摘要：

  Trimetoquinol (TMQ, 1) is a unique catecholamine with a strong stereodependence for agonism at beta-adrenergic (S much greater than R) and antagonism at thromboxane A(2)/prostaglandin H-2 (TP; R much greater than S) receptors. Our laboratory has reported the effects of N-alkylation and modification of the trisubstituted benzyl group in these receptor systems. For iodinated derivative 5, maintaining potency in TP receptor systems (112%) was coupled with maintaining limited potency in beta-adrenergic receptor systems (34% for beta(1) and 47% for beta(2)) In this study, several diverse TMQ derivatives were prepared to probe for binding interactions specific to a particular receptor system. Planar amidine 2, which was designed to explore the importance of TMQ's chiral center, showed a dramatic loss of potency (<1%) in each receptor system. Likewise, the homologation of a previously described N-benzyl derivative (3) to the N-phenylethyl derivative 4 also showed reduced potency (<3%) in both receptor systems. However, modification of the trimethoxybenzyl group of TMQ to a 4-hydroxy-3-nitrobenzyl group (7) provided a unique lead for TMQ derivatives with significant potency in TP receptor systems (91%) and reduced potency in beta-adrenergic receptor systems (4% for beta(1) and 19% for beta(2)).

  DOI：

  10.1021/jm950896w

文献信息

• Synthesis and Evaluation of Trimetoquinol Derivatives:  Novel Thromboxane A₂/Prostaglandin H₂ Antagonists with Diminished β-Adrenergic Agonist Activity
  作者：Jeffrey J. Christoff、Luke Bradley、Duane D. Miller、Longping Lei、Fernando Rodriguez、Paul Fraundorfer、Karl Romstedt、Gamal Shams、Dennis R. Feller

  DOI：10.1021/jm950896w

  日期：1997.1.1

  Trimetoquinol (TMQ, 1) is a unique catecholamine with a strong stereodependence for agonism at beta-adrenergic (S much greater than R) and antagonism at thromboxane A(2)/prostaglandin H-2 (TP; R much greater than S) receptors. Our laboratory has reported the effects of N-alkylation and modification of the trisubstituted benzyl group in these receptor systems. For iodinated derivative 5, maintaining potency in TP receptor systems (112%) was coupled with maintaining limited potency in beta-adrenergic receptor systems (34% for beta(1) and 47% for beta(2)) In this study, several diverse TMQ derivatives were prepared to probe for binding interactions specific to a particular receptor system. Planar amidine 2, which was designed to explore the importance of TMQ's chiral center, showed a dramatic loss of potency (<1%) in each receptor system. Likewise, the homologation of a previously described N-benzyl derivative (3) to the N-phenylethyl derivative 4 also showed reduced potency (<3%) in both receptor systems. However, modification of the trimethoxybenzyl group of TMQ to a 4-hydroxy-3-nitrobenzyl group (7) provided a unique lead for TMQ derivatives with significant potency in TP receptor systems (91%) and reduced potency in beta-adrenergic receptor systems (4% for beta(1) and 19% for beta(2)).