(+/-)-13-amino-(1H-indol-4-yl)-1,8,11-trioxa-5-azatridecan-3-ol | 1335302-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-13-amino-(1H-indol-4-yl)-1,8,11-trioxa-5-azatridecan-3-ol
• 英文别名: 1-[2-[2-(2-aminoethoxy)ethoxy]ethylamino]-3-(1H-indol-4-yloxy)propan-2-ol
• CAS: 1335302-86-7
• 化学式: C₁₇H₂₇N₃O₄
• 分子量: 337.419
• InChiKey: MBHVZVQGUAQNPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BODIPY630/650−X-NHS ester 、 (+/-)-13-amino-(1H-indol-4-yl)-1,8,11-trioxa-5-azatridecan-3-ol 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以68%的产率得到(+/-)-N-[3-hydroxy-1-(1H-indol-4-yl)-1,8,11-trioxa-5-azatridecan-13-yl]-6-(2-(2-(4,4-difluoro-4,4a-dihydro-5-(thiophen-2-yl)-4-bora-3a,4a-diaza-s-indacene-3-yl)vinyl)phenoxyacetamido)hexanamide
  参考文献：
  名称：

  Synthesis and Characterization of High-Affinity 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene-Labeled Fluorescent Ligands for Human β-Adrenoceptors

  摘要：

  The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human beta-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity beta-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log K-D of -9.53 and -8.46 as an antagonist of functional beta 2- and beta 1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human beta 2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent beta 2-selective antagonist 3-(isopropylamino)-1-[(7-methyl-4-indanyl)oxy]-butan-2-ol (ICI 118551) (J. Cardiovasc. Pharmacol. 1983, 5,430-437.)

  DOI：

  10.1021/jm2008562
• 作为产物：
  描述：

  (+/-)-benzyl 2-(2-(2-(3-(1H-indol-4-yloxy)-2-hydroxypropylamino)ethoxy)ethoxy)ethylcarbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以88%的产率得到(+/-)-13-amino-(1H-indol-4-yl)-1,8,11-trioxa-5-azatridecan-3-ol
  参考文献：
  名称：

  Synthesis and Characterization of High-Affinity 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene-Labeled Fluorescent Ligands for Human β-Adrenoceptors

  摘要：

  The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human beta-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity beta-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log K-D of -9.53 and -8.46 as an antagonist of functional beta 2- and beta 1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human beta 2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent beta 2-selective antagonist 3-(isopropylamino)-1-[(7-methyl-4-indanyl)oxy]-butan-2-ol (ICI 118551) (J. Cardiovasc. Pharmacol. 1983, 5,430-437.)

  DOI：

  10.1021/jm2008562