Synthesis of 2,10-diphenyl-2H-pyridazino[4,5-b]quinolin-1-one and 2,3-dihydro-9-phenyl-2-phenylamino-1H-pyrrolo[3,4-b]quinolin-1-one derivatives as peripheral-type benzodiazepine receptor ligands

M. Anzini, A. Cappelli, S. Vomero, A. Cagnotto, M. Skorupska

Research output: Contribution to journalArticle

Abstract

The reaction of 2-chloromethyl-3-ethoxycarbonyl-4-phenylquinoline with phenylhydrazine, afforded 2,3-dihydro-9-phenyl-2-phenylamino-1H-pyrrolo[3,4-b]quinolin-1-one derivatives 2 along with a major amount of 3-ethoxycarbonyl-4-phenylquinoline-2-carboxaldehyde phenylhydrazone 4a. The geometric isomers of phenylhydrazone 4a, displaying solvent-dependent E-Z isomerism, were isolated, characterized by 1H-nmr and mass spectra, and the Z-form easily cyclized to pyridazino[4,5-b]quinoline derivative 5a. Analogously, compounds 2b, 2c, 4b, 5b and 5c were obtained. The title compounds were tested as potential ligands for central and peripheral-type of benzodiazepine receptors, and the results are reported.

Original languageEnglish
Pages (from-to)1111-1115
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume29
Issue number5
Publication statusPublished - 1992

ASJC Scopus subject areas

  • Organic Chemistry

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