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

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...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 29; no. 5; pp. 1111 - 1115
Main Authors ANZINI, M, CAPPELLI, A, VOMERO, S, CAGNOTTO, A, SKORUPSKA, M
Format Journal Article
LanguageEnglish
Published TAMPA HETERO CORPORATION 01.08.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BINDING-SITES
AFFINITY
RAT-BRAIN
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Summary: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 H-1-nmr and mass spectra, and the Z-form easily cyclized to pyridazino[4,5-b]quinoline derivative 5a. Analogously, compounds 2b, 2c, 4b, 4c, 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.
ISSN:0022-152X
DOI:10.1002/jhet.5570290513