(+/-)-1-(2-allylphenoxy)-3-(2-aminomethylamino)propan-2-ol | 66825-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-1-(2-allylphenoxy)-3-(2-aminomethylamino)propan-2-ol
• 英文别名: 1-[(2-Aminoethyl)amino]-3-[2-(prop-2-EN-1-YL)phenoxy]propan-2-OL；1-(2-aminoethylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
• CAS: 66825-08-9
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: RWRGAVDUFICLTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4-氯苯甲酰基)氨基]乙酸乙酯 、 (+/-)-1-(2-allylphenoxy)-3-(2-aminomethylamino)propan-2-ol 生成 N-({2-[3-(2-Allyl-phenoxy)-2-hydroxy-propylamino]-ethylcarbamoyl}-methyl)-4-chloro-benzamide
  参考文献：
  名称：

  DE2745222

  摘要：

  公开号：
• 作为产物：
  描述：

  [(2-烯丙基苯氧基)甲基]环氧乙烷 在 盐酸 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (+/-)-1-(2-allylphenoxy)-3-(2-aminomethylamino)propan-2-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

• Synthesis and Characterization of High-Affinity 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene-Labeled Fluorescent Ligands for Human β-Adrenoceptors
  作者：Jillian G. Baker、Luke A. Adams、Karolina Salchow、Shailesh N. Mistry、Richard J. Middleton、Stephen J. Hill、Barrie Kellam

  DOI：10.1021/jm2008562

  日期：2011.10.13

  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.)
• DE2745222
  申请人：——

  公开号：——

  公开（公告）日：——