Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs

Abstract

We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogenation under oxygen atmosphere. Therefore, the ellipticine quinone analogs possessing substitution at the 8- and/or 9-positions were synthesized using this method. In total, 14 compounds were evaluated for antiproliferative activity against HCT-116 and HL-60 cell lines; 9-nitroellipticine quinone was found to have superior activity compared to calothrixin B.

Keywords: Antiproliferative activity; Carbazole-1,4-quinone; Ellipticine quinone; Pyrido[4,3-b]carbozole-5,11-quinone; Ring-Closing Metathesis.