Synthesis and Anticoagulant Activity of New Functionalized 4H-Pyrrolo[3,2,1-ij]quinolin-2-ones

The reduction of 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones with aqueous hydrazine hydrate selectively involved the C-1=O carbonyl group to give the corresponding 4,4,6-trimethyl-4H-pyrrolo-[3,2,1-ij]quinolin-2(1H)-ones within a few hours. The reduction products were condensed with aldehydes and acetone to afford new 1-[(het)arylmethylidene]- and 1-(propan-2-ylidene)-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones in 59-78% yield. The reaction of 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones with N,N-di-methylformamide dimethyl acetal, followed by transamination with primary amines led to the formation of 1-{[(het)arylamino]methylidene}-4H-pyrrolo[3,2,1-ij]quinolin-2-ones in 65-83% yield. The synthesized compounds were evaluated for their anticoagulant activity by measuring inhibition of blood coagulation factors Xa and XIa.

Automated summary

In this study, new compounds with different skeletal structures were synthesized through selective reduction reactions and their anticoagulant activity was evaluated.