Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 8, Pages 1811-1818Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403549
Keywords
Medicinal chemistry; Drug design; Antitumor agents; Nitrogen heterocycles; DNA; Cross-coupling
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A facile synthesis of new antitumor [4,5-bc]carbazole-amonafide derivatives is described. These compounds represent a new class of structural hybrids that contain the medicinally important carbazole and amonafide cores. The synthesis involves a Suzuki-Miyaura coupling of bromoamonafide with arylboronic acid reagents followed by the introduction of an azide group and subsequent regiospecific thermal nitrene insertion to yield carbazole-amonafide hybrids in good yields. Preliminary antiproliferative assays against cancer and benign cell lines identified compounds with selective antitumor activity that exhibited submicromolar IC50 values.
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