1,5-dimethyl-6H-pyridazino[4,5-b]carbazole, a 3-aza bioisoster of the antitumor alkaloid olivacine.
A series of b-fused carbazoles structurally related to pyrido[4,3-b]carbazole-type alkaloids was prepared, utilizing the Diels-Alder reaction of 1-methylpyrano[3,4-b]indol-3(9H)-one with electron-deficient acetylenic dienophiles as the key step. The title compound (14) thus obtained in only four steps represents a new 3-aza analog of the antitumor natural product, olivacine.
Haider
Norbert
N
Institute of Pharmaceutical Chemistry, University of Vienna, Austria. norbert.haider@univi.ac.at
Sotelo
Eddy
E
D000470:Alkaloids / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry*; D002227:Carbazoles / Q000737:chemistry*; D004611:Ellipticines / Q000737:chemistry*; D011724:Pyridazines / Q000737:chemistry*
D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D002227:Carbazoles; D004611:Ellipticines; D011724:Pyridazines; C011521:olivacine