Nitrogen Bridgehead Compounds. 44. New Antiallergic 4-Pyrido[1,2-a]pyrimidin-4-ones

István Hermecz, Agnes Horváth, Zoltán Mészáros, Christine De Vos, Ludovic Rodriguez

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21 Citations (Scopus)


The weak antiallergic activity of 6-methyl-4-oxo-6,7, 8,9-tetrahydro-4if-pyrido[1, 2-o]pyrimidine-3-carboxylic acid (1) in the rat reaginic passive cutaneous anaphylaxis test was enhanced by the introduction of an (arylamino)methylene moiety into position 9 of the pyridopyrimidine ring. Compound 34, (+)-6(S)-methyl-9-[(m-methylphenyl)-hydrazono]-4-oxo-4H-pyrido[1, 2-α]pyrimidine-3-carboxylic acid, displayed about 10000 times the activity of the starting compound 1. A structure-activity relationship study of 9-[(arylamino)methylene]tetrahydropyridopyrimidine-3-carboxylic acids resulted in conclusions similar to those found for the 9-(arylhydrazono)tetrahydroand 9-(arylamino)dihydropyridopyrimidine series. Replacement of the 3-carboxy group of 9-(phenylhydrazono)-tetrahydropyridopyrimidin-4-ones with anacrylic acid moiety caused slight increases in potency. In the 6-methyl-substituted series, a high stereospecificity was observed between the enantiomers with 6S and 6fi absolute configurations, the former being responsible for the antiallergic activity. The effects of some 9-[(arylamino)-methylene]tetrahydropyridopyrimidine-3-carboxylic acids on the rat passive peritoneal anaphylaxis test were also investigated.

Original languageEnglish
Pages (from-to)1253-1259
Number of pages7
JournalJournal of Medicinal Chemistry
Issue number10
Publication statusPublished - Nov 1984

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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