Thieno[2,3-c]chinoline – Synthese und biologische Prüfung
Thieno[2,3-c]quinolines – synthesis and biological investigation
pH-Dependant reduction of the methyl 3-(2-nitrophenyl)thiophene-2-carboxylate (3), obtained by Suzuki cross-coupling of the methyl 3-iodothiophene-2-carboxylate with 2-nitrophenyl boronic acid yields the cyclic hydroxamic acid 4 and the lactam 5, respectively. The lactam 5 is also formed by reacting the compound 2 with pinacolato 2-aminophenylboronate. The 4-chlorothieno[2,3-c]quinoline 6 is formed from the lactam 5 by heating with POCl3/PCl5. Melting of 6 with the novaldiamine base in phenol gives the chloroquine analogue 7, whereas the amodiaquine and the cycloquine analogues 8 and 9 are obtained using phenol Mannich bases. The hydroxamic acid 4 has a moderate effect on eicosanoid biosynthesis in human whole blood. The growth of the chloroquine resistent Plasmodium falciparum strain Dd2 is inhibited by the pyronaridine derivative 9 with an IC50-value of 650 nM.
Document Type: Research Article
Affiliations: 1: Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Beethovenstraße 55, Braunschweig, D-38106, Germany, Email: [email protected] 2: Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Braunschweig, Germany 3: Institut für Pharmazeutische Chemie der Martin-Luther-Universität Halle-Wittenberg, Halle-Wittenberg, Germany 4: Biochemisches Institut der Universitätsklinik Gießen, Gießen, Germany
Publication date: 01 June 2004
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