2-[(9H-fluoren-9-yl)methoxycarbonyl]-6,7-dimethoxy-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline | 880474-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[(9H-fluoren-9-yl)methoxycarbonyl]-6,7-dimethoxy-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 880474-96-4
• 化学式: C₃₃H₃₀N₂O₆
• 分子量: 550.611
• InChiKey: LGSSILLJOLOJOU-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  723.8±60.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[(9H-fluoren-9-yl)methoxycarbonyl]-6,7-dimethoxy-1-(4-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 三溴化硼 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 溶剂黄146 、 calcium carbonate 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 8.0h， 生成 甘氨酸酰胺,5-羰基-L-脯氨酰-L-组氨酰-L-色氨酰-L-丝氨酰-L-组氨酰-D-精氨酰-L-色氨酰-L-酪氨酰-L-脯氨酰-
  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：

  1,2,3,4-四氢-6,7-二甲氧基-1-[(4-硝基苯基)甲基]异喹啉 、 氯甲酸-9-芴基甲酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到2-[(9H-fluoren-9-yl)methoxycarbonyl]-6,7-dimethoxy-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