(2013) Kinetic and in silico analysis of thiazolidin-based inhibitors of α-carbonic anhydrase

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The Schiff bases derived from quinoline-8-carbaldehyde and substituted aromatic amines were used in the synthesis of C-8 substituted quinolines. 3-Aryl-2-(8-quinolinyl)-4-thiazolidinones were prepared from obtained aldimines by means of the cyclocondensation of mercapto acids. A series of 4-N-arylamino-4-(8-quinolinyl)-1-butenes was synthesized through the addition of the Grignard reagent (allylmagnesium bromide) to the double bond C=N of these aldimines. The structure of the prepared compounds was established on the basis of their elemental analyses and spectral data.

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New derivatives of -substituted furans were prepared in high yields from easily available -furfurylidenbenzilamines via nucleophilic C-allylation. The homoallylamines obtained this way were used for the synthesis of some polyfunctional aminobutene derivatives. In addition, 4-thiazolidinones some of which are hetaryl substituted at the 2-position were prepared by the reaction of mercapto acids with quinoline carboxaldehydes and p-phenetidine. All new products were fully characterized. Allylierungs-und Heterocycloadditionsreaktionen von Aldiminen: Furan-und ChinolincarboxaldehydeZusammenfassung. Aus den leicht zuga Ènglichen -Furfurylidenbenzilaminen wurden durch nucleophile C-Allylierung neue Derivative -substituierter Furane mit hohen Ausbeuten dargestellt. Die dabei gewonnenen Homoallylamine wurden fu È r die Synthese von polyfunktionalen Aminobutenderivaten eingesetzt. Daru Èber hinaus wurden durch Reaktion von Merkaptosa Èuren mit Chinolincarboxaldehyden und p-Phenetidin an der 2-Stelle heterosubstituierte 4-Thiazolidinone gebildet. Alle Produkte wurden entsprechend charakterisiert.