ABSTRACT
A series of new 7- and 4-azaindolo[1,2-f]phenanthridines were synthesized by a domino Pd(0)-catalyzed reaction, which involves three sequential steps: C-N coupling, hydroamination, and intramolecular C-H arylation. The products show promising fluorescence properties with high quantum yields (12-65%).
ABSTRACT
A highly selective and efficient method for the synthesis of 5-trifluoromethylated and 5-perfluoroalkylated pyrazoles has been developed which relies on the cyclization of hydrazine dianions with ethyl perfluorocarboxylates. The pyrazoles prepared were evaluated as potential inhibitors of alkaline phosphatases, namely human tissue non-specific alkaline phosphatase (h-TNAP) and tissue specific intestinal alkaline phosphatase (IAP). Most pyrazole derivatives inhibited h-IAP more markedly than h-TNAP and had minor effects on nucleotide pyrophosphatase/phosphodiesterases. Therefore, the compounds appear as potential selective inhibitors of h-IAP.
Subject(s)
Chemistry, Organic/methods , Hydrazones/chemistry , Pyrazoles/chemical synthesis , Agrochemicals/chemistry , Alkaline Phosphatase/antagonists & inhibitors , Alkaline Phosphatase/metabolism , Animals , Anions , COS Cells , Chlorocebus aethiops , Cyclization , Enzyme Inhibitors/pharmacology , Humans , Isoxazoles/chemical synthesis , Isoxazoles/chemistry , Pharmaceutical Preparations/chemistry , Pyrazoles/chemistry , Pyrophosphatases/antagonists & inhibitors , Pyrophosphatases/metabolism , Structure-Activity RelationshipABSTRACT
A new and convenient method for the synthesis of indolo[1,2-f]phenanthridines via palladium-catalyzed domino C-N coupling/hydroamination/C-H arylation reactions was developed. The reactions allow for the synthesis of various phenanthridines in good yields from easily accessible starting materials using a single palladium catalyst.