Premium
Synthesis and Authentication of Iodoazidophenpyramine, a Photoaffinity Reporter Ligand Previously used for Histamine H 1 ‐Receptor Labelling
Author(s) -
Sorba Giovanni,
Tertiuk Wasyl,
Ganellin C. Robin
Publication year - 1995
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19953280909
Subject(s) - chemistry , phenylacetic acid , labelling , ligand (biochemistry) , stereochemistry , photoaffinity labeling , histamine , receptor , histamine h1 receptor , chemical synthesis , combinatorial chemistry , histamine receptor , biochemistry , pharmacology , biology , antagonist , in vitro
The synthesis is described of aminophenpyramine ( 7 ) ( N ‐{5‐[2‐(4‐aminophenyl)ethananmido]pentanyl}‐ N ′‐(4‐methoxybenzyl)‐ N ‐methyl‐ N ′‐(2‐pyridinyl)‐1,2‐ethandiamine), its monoiodo‐ and diiodo‐derivatives ( 8 and 9 ), and iodoazidophenpyramine ( 1 ). The last compound is synthesised by two different routes to confirm the identity of the [ 125 I]iodinated ligand previously made only in solution and used for characterisation of the histamine H 1 ‐receptor protein. The procedures employ the novel intermediates 4‐amino‐3‐iodo‐phenylacetic acid ( 11 ) and 4‐azido‐3‐iodo‐phenylacetic acid ( 13 ). They have general applicability to the synthesis of non‐radioactive iodinated photoaffinity receptor ligands which may be required for chemical authentication of the corresponding radiolabelled compounds.