6,7-bis(ethoxycarbonyloxy)-2-[(9H-fluoren-9-yl)methoxycarbonyl]-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline | 880475-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-bis(ethoxycarbonyloxy)-2-[(9H-fluoren-9-yl)methoxycarbonyl]-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 9H-fluoren-9-ylmethyl 6,7-bis(ethoxycarbonyloxy)-1-[(4-nitrophenyl)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 880475-00-3
• 化学式: C₃₇H₃₄N₂O₁₀
• 分子量: 666.684
• InChiKey: HLMJLQYGBIOQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6,7-bis(ethoxycarbonyloxy)-2-[(9H-fluoren-9-yl)methoxycarbonyl]-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 氢气 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 6.0h， 生成 5-氟-2-碘苯(甲)醛
  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-[(9H-fluoren-9-yl)methoxycarbonyl]-6,7-dimethoxy-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 6,7-bis(ethoxycarbonyloxy)-2-[(9H-fluoren-9-yl)methoxycarbonyl]-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline
  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