Synthesis and properties of novel hybrid molecules bearing 4H-pyrrolo[3,2,1-ij]quinolin-2-one and thiazole moieties

A reaction of 2-(4,4,6-trimethyl-2-oxo-4 H -pyrrolo[3,2,1- ij ]quinoline-1-ylidene)-hydrazinocarbothioamides with α-halocarbonyl compounds, such as ethyl bromocetate and 2-bromoacetophenone derivatives, afforded a series of novel 4,4,6-trimethyl-2-oxo-4 H -pyrrolo[3,2,1- ij ]quinoline-1(2 H )-ylidene)hydrazinylidene)thiazolidin-4-ones and 4,4,6-trimethyl-1-(2-(4-arylthiazol-2-yl)hydrazinylidene)-4 H -pyrrolo[3,2,1- ij ]quinolin-2(1 H )-ones. The synthesized compounds exist in the form of Z -isomers. Primary screening in vitro of inhibitory activity towards blood clotting factors Xa and XIa was carried out, revealing that the thiazole derivative bearing the 4-chlorophenyl substituent at the thiazole moiety exhibits a sufficiently high anticoagulant activity towards these blood clotting factors.