Synthesis and antibacterial evaluation of new pyrrolo[3’,4’:3,4]pyrrolo[1,2-a]quinoline and pyrrolo[3',4':3,4]pyrrolo[2,1-a]isoquinoline derivatives

Abstract

Two series of new fused pyrrolo [3',4':3,4]pyrrolo[1,2-a]quinoline and pyrrolo [3',4':3,4]pyrrolo[2,1-a]isoquinoline derivatives were synthesized and evaluated for the antimicrobial activity. The synthetic approach involves cycloimmonium ylides as 1,3-dipol intermediates. The structures of all synthesized compounds were proved by analytical and spectroscopic data. Crystal structure of compound 11a has been also determined by single crystal XRD. The synthesized compounds were evaluated for their expected antimicrobial activity against Staphylococcus aureus ATCC25923, Escherichia coli ATCC25922 and Candida albicans ATCC10231, but no one showed activity against all the reference strains.

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives

“…Initially, for the introduction of a 4-substituted phenacyl substituent, salts 3a – c and 5a – c were synthesized by the direct N -alkylation of isoquinoline and quinoline, respectively, using para -substituted 2-bromoacetophenones 2a – c ( Scheme 1 and Scheme 2 ) [ 28 ]. The spectral data of salts 2a – b and 3a – b are not reported herein, being in agreement with the ones in the existing literature [ 29 , 30 ].…”

“…Protons 2 and 10 produce signals at δ = 4.26 ppm and δ = 4.32 ppm, respectively ( Table 1 ). The small coupling for the H1 proton (δ = 6.04 ppm, J = 2.5 Hz) suggests a trans position relative to proton H2 [ 20 , 21 , 29 ]. The large values for the coupling constants J 2,3 (8.0 Hz) and J 3,10 (9.5 Hz) suggests that hydrogen atoms H2, H3 and H10 lay on the same side of the tetrahydropyrrole ring, but on the opposite side of H1 ( Scheme 3 , Table 1 ).…”

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

“…Having in view the biological potential of quinoline and sulfonamide scaffolds (especially antimicrobial) [9][10][11][12][13][14][15], as well as those one of quinoline-sulfonamide combined scaffold (especially anti-HIV-1) [16], we decide to combine the pharmacophoric properties of these core scaffolds with the complementary biological properties of counter cation M 2+ (M 2+ : Zn 2+ , Cu 2+ , Co 2+ and Cd 2+ ), with the final goal of obtaining better biological activity and better pharmacokinetic properties for our compounds. In this respect, we design two new classes of hybrid quinoline-sulfonamide complexes, namely N-(quinolin-8-yl)-4-R-benzene sulfonamide metal (II) (QBSC) and N-(quinolin-8-yl)-quinoline -8-sulfonamide metal (II) (QQSC), Scheme 1.…”

“…Quinoline based compounds are small molecules of huge importance from pharmacological point of view, having a wide range of biological activities such as antiplasmodial and antimalarial, antibacterial, antifungal, antitubercular, anti-HIV, antiviral (including against COVID-19), etc. [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. A special class of quinoline derivatives which pay a particularly attention on scientific community, are quinoline-sulfonamide complexes ( QSC ), studied especially for their fotoluminiscent (mostly fluorescent) properties [ 17 , 18 , 19 , 20 , 21 , 22 , 23 ].…”

“…Encouraged by our recent results in the field of (di)azine with antimicrobial activity [ 11 , 15 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ], we report here the design, synthesis, antibacterial and antifungal evaluation of some newly hybrid quinoline-sulfonamide complexes.…”