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

• Published in: Russian journal of organic chemistry Vol. 58; no. 9; pp. 1225 - 1232
• Main Authors: Novichikhina, N. P., Ashrafova, Z. E., Ledenyova, I. V., Podoplelova, N. A., Panteleev, M. A., Shikhaliev, Kh. S.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.09.2022; Springer Nature; Springer Nature B.V
• Subjects: Aldehydes; Amines; Anticoagulants; Blood coagulation; Carbonyl groups; Carbonyls; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Dimethyl acetals; Dimethylformamide; Hydrazines; Organic Chemistry; Physical Sciences; Quinoline; Reduction; Science & Technology; factors Xa and XIa; quinolin-2-one; 4; pyrrolo[3,2,1; Wolff–Kishner reaction; anticoagulant activity; ANTIBACTERIAL ACTIVITIES; STRATEGY; Wolff-Kishner reaction; RECEPTOR; 2; 1-ij]quinolin-2-one; AGENTS; INHIBITORS; DERIVATIVES; SELECTIVITY; 4H-pyrrolo
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428022090056

The reduction of 4,4,6-trimethyl-4 H -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-4 H -pyrrolo­[3,2,1- ij ]quinolin-2(1 H )-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)-4 H -pyrrolo[3,2,1- ij ]quinolin-2(1 H )-ones in 59–78% yield. The reaction of 4,4,6-trimethyl-4 H -pyrrolo[3,2,1- ij ]quinolin-2(1 H )-ones with N , N -di­methylformamide dimethyl acetal, followed by transamination with primary amines led to the formation of 1-{[(het)arylamino]methylidene}-4 H -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.