(+/-)-13-amino1-(naphthylen-1-yl)-1,8,11-trioxa-5-azatridecan-3-ol | 1335302-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-13-amino1-(naphthylen-1-yl)-1,8,11-trioxa-5-azatridecan-3-ol
• 英文别名: 1-[2-[2-(2-Aminoethoxy)ethoxy]ethylamino]-3-naphthalen-1-yloxypropan-2-ol
• CAS: 1335302-75-4
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: MLPNFYFIANCKRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+/-)-benzyl 2-(2-(2-(2-hydroxy-3-(naphthylen-1-yloxy)propylamino)ethoxy)ethoxy)ethylcarbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以97%的产率得到(+/-)-13-amino1-(naphthylen-1-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

文献信息

• [EN] PHOTOAFFINITY PROBES<br/>[FR] SONDES DE PHOTOAFFINITÉ
  申请人：PROMEGA CORP

  公开号：WO2020191339A1

  公开（公告）日：2020-09-24

  Provided herein are compositions and methods for photoaffinity labeling of molecular targets. In particular, probes that specifically interact with cellular targets based on their affinity and are then covalently linked to the cellular target via a photoreactive group (PRG) on the probe.

  本文件提供了用于光亲和标记分子靶点的组合物和方法。特别是，基于它们的亲和力与细胞靶点特异性相互作用的探针，然后通过探针上的光反应组（PRG）与细胞靶点共价连接。