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Drug‐induced modifications of the immune response part 9 4‐(Arylamino)‐2,5‐dihydro‐2‐oxo‐ N ‐( trans ‐2‐phenylcycolopropyl)furan‐3‐carboxamides as Novel Antiallergic Compounds
Author(s) -
Georgiev Vassil St.,
Mack Robert A.,
Walter David J.,
Radov Lesley A.,
Baer Jane E.
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700609
Subject(s) - chemistry , histamine , furan , stereochemistry , amine gas treating , drug , pharmacology , organic chemistry , medicine
The synthesis and antiallergic activity of a series of 4‐(arylamino)‐2,5‐dihydro‐2‐oxo‐ N ‐( trans ‐2‐phenyl‐cyclopropyl)furan‐3‐carboxamides 10 are described. Treatment of N ‐substituted 2‐amino‐4,5‐dihydro‐4‐oxofuran‐3‐carboxylic acids 9 with chlorooxobis(2‐oxo‐1,3‐oxazolidin‐3‐yl)phosphorus ( 2 ) and an appropriate aromatic amine in the presence of Et 3 N, resulted in a novel 3(2 H )‐furanone‐→2(5 H )‐furanone rearrangement that led to the facile preparation of the new amides 10 . The latter exerted a potent antiallergic activity when tested in the dermal vascular permeability and active anaphylaxis assays in rats. The most active compound 10b inhibited the action of serotonin, histamine, and bradykinin by 94, 92, and 100%, respectively, when administered intraperitoneally to rats at doses of 100 mg/kg. The present series of 10 represents a novel class of antiallergic agents.