Reaction of 1‐Phenacylidene pyrrolo[3, 2, 1‐ij]quinolin‐2‐ones with Cyclic/Acyclic Enaminones and the Anticoagulant Activity of Synthesized Pyrrole‐Quinoline Derivatives. Issue 46 (8th December 2022)

• Record Type: Journal Article
• Authors: Skoptsova, Anna A.; Shestakov, Alexander S.; Ledenyova, Irina V.; Stolpovskaya, Nadezhda V.; Podoplelova, Nadezhda A.; Panteleev, Mikhail A.; Paponov, Boris V.; Sidorenko, Oleg E.; Shikhaliev, Khidmet S.; Novichikhina, Nadezhda P.
• Is Part Of: ChemistrySelect. Volume 7:Issue 46(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-08
• Subjects: Anticoagulant activity -- Atropoisomers -- Enaminones -- Pyrrole -- Tautomerism; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202200730
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A convenient strategy for the synthesis of pyrroles lineary linked to 4 H ‐pyrrolo[3, 2, 1 ‐ij ]quinolin‐2(1 H )‐ones is presented. The cyclization of ( E )‐1‐(2‐oxo‐2‐phenylethylidene)‐4 H ‐pyrrolo[3, 2, 1‐ ij ]quinolin‐2‐ones with linear and cyclic enaminones proceeds both in the presence of p ‐toluenesulfonic acid and triethylamine. The obtained compounds are characterised by atropoisomerism and keto‐enol tautomerism. The synthesized 1‐(2‐phenyl‐1 H ‐pyrrol‐3‐yl)‐4 H ‐pyrrolo[3, 2, 1‐ ij ]quinolin‐2(1 H )‐ones were studied for anticoagulant activity. Abstract : A series of structurally fascinating novel pyrrole‐pyrrolo[3, 2, 1‐ ij ]quinolin‐2‐ones hybrids have been synthesized via the reaction of 1‐phenacylidene pyrrolo[3, 2, 1‐ij]quinolin‐2‐ones with various cyclic/acyclic enaminones. All reactions proceeded in good yields and the resulting compounds were characterized by different spectroscopic techniques, including X‐ray diffraction analysis, and exist as atropodiastereomers and keto‐enol tautomers. The anticoagulant activity of the synthesized compounds was evaluated towards coagulation factors Xa and XIa in comparison with rivaroxaban.