Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3 ',4 '-tri-subsituted-1,2-dihydro-4H,4 ' H-spiro[isoquinoline-3,5 '-isoxazol]-4-ones

Ben Hadda T., Rahima B., Kerbal A., Bennani B., Al Houari G., Baba B. F. , ...Daha Fazla

ARKIVOC, ss.1-13, 2008 (SCI İndekslerine Giren Dergi) identifier identifier


Synthesis of a series of fourteen novel 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H-spiro[isoquinoline-3,5'-isoxazol]-4-ones was accomplished in good yield by regio and stereoselective 1,3-dipolar cycloaddition of p-R-2-benzadoxime 4-8 with dipolarophiles (3Z)-3-[(4-substituted-phenyl)methylidene]-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ones 1-3. The structure of the isolated products 9-23 was established through different spectroscopic techniques. X-Ray crystal structure analysis of one of the products confirms the structure and the selective region and stereochemistry of this cycloaddition. Their antitubercular activity is also evaluated.