N-[2-(3,4-dimethoxyphenyl)ethyl]-4-benzoylphenylacetamide | 880475-07-0

• 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: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-benzoylphenylacetamide
• 英文别名: N-(3,4-Dimethoxyphenethyl)-4-benzoylphenylacetamide；2-(4-benzoylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• CAS: 880475-07-0
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: JKOMIMIRUULWBH-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  632.7±55.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-dimethoxyphenyl)ethyl]-4-benzoylphenylacetamide 在 mercury(II) perchlorate 、 三氟化硼乙醚 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 4-(6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-1-yl)benzophenone hydrobromide
  参考文献：
  名称：

  1-Benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diols as novel affinity and photoaffinity probes for β-adrenoceptor subtypes

  摘要：

  Trimetoquinol (TMQ, 1) is a potent non-selective beta-adrenoceptor (beta-AR) agonist possessing a tetrahydroisoquinoline (THI) structure. The binding site for 1-trimethoxybenzyl group of 1, which distinguishes it from classical catecholamines, is unknown. Affinity and photoaffinity labeled compounds are good tools to determine the exact interaction between a ligand and a specific amino acid(s) in a receptor. In this study, we designed and synthesized a series of affinity 6, 12, 18, and photoaffinity 24, 29 labeled analogues of TMQ All of these compounds were full agonists and demonstrated an equal or greater binding affinity and functional activity as compared to TMQ on beta(1)-, beta(2)-, and beta(3)-AR. Washout experiments on Chinese hamster ovary (CHO) cells expressing hu beta(2)-AR were helpful in identifying the isothiocyanate 18 and the azide 24 as very effective affinity and photoaffinity labels at this receptor subtype. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.027
• 作为产物：
  描述：

  2-(4-苯甲酰基苯基)乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 N-[2-(3,4-dimethoxyphenyl)ethyl]-4-benzoylphenylacetamide
  参考文献：
  名称：

  1-Benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diols as novel affinity and photoaffinity probes for β-adrenoceptor subtypes

  摘要：

  Trimetoquinol (TMQ, 1) is a potent non-selective beta-adrenoceptor (beta-AR) agonist possessing a tetrahydroisoquinoline (THI) structure. The binding site for 1-trimethoxybenzyl group of 1, which distinguishes it from classical catecholamines, is unknown. Affinity and photoaffinity labeled compounds are good tools to determine the exact interaction between a ligand and a specific amino acid(s) in a receptor. In this study, we designed and synthesized a series of affinity 6, 12, 18, and photoaffinity 24, 29 labeled analogues of TMQ All of these compounds were full agonists and demonstrated an equal or greater binding affinity and functional activity as compared to TMQ on beta(1)-, beta(2)-, and beta(3)-AR. Washout experiments on Chinese hamster ovary (CHO) cells expressing hu beta(2)-AR were helpful in identifying the isothiocyanate 18 and the azide 24 as very effective affinity and photoaffinity labels at this receptor subtype. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.027

文献信息

• Substituted Tetrahydroisoquinoline Compounds for Cancer Therapy
  申请人：Miller D. Duane

  公开号：US20080033007A1

  公开（公告）日：2008-02-07

  Disclosed are compounds that are effective for selectively killing cancer cells. Compounds have been demonstrated to be especially effective for killing glioma cells, while exhibiting low toxicity to normal cells.

  本发明揭示了一些能够有效选择性杀死癌细胞的化合物。这些化合物已被证明对于杀死胶质瘤细胞特别有效，同时对正常细胞的毒性较低。
• 1-Benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diols as novel affinity and photoaffinity probes for β-adrenoceptor subtypes
  作者：Victor I. Nikulin、Igor M. Rakov、Joseph E. De Los Angeles、Ratna C. Mehta、LeNe’Sheya Y. Boyd、Dennis R. Feller、Duane D. Miller

  DOI：10.1016/j.bmc.2005.12.027

  日期：2006.3

  Trimetoquinol (TMQ, 1) is a potent non-selective beta-adrenoceptor (beta-AR) agonist possessing a tetrahydroisoquinoline (THI) structure. The binding site for 1-trimethoxybenzyl group of 1, which distinguishes it from classical catecholamines, is unknown. Affinity and photoaffinity labeled compounds are good tools to determine the exact interaction between a ligand and a specific amino acid(s) in a receptor. In this study, we designed and synthesized a series of affinity 6, 12, 18, and photoaffinity 24, 29 labeled analogues of TMQ All of these compounds were full agonists and demonstrated an equal or greater binding affinity and functional activity as compared to TMQ on beta(1)-, beta(2)-, and beta(3)-AR. Washout experiments on Chinese hamster ovary (CHO) cells expressing hu beta(2)-AR were helpful in identifying the isothiocyanate 18 and the azide 24 as very effective affinity and photoaffinity labels at this receptor subtype. (c) 2005 Elsevier Ltd. All rights reserved.