Ultrasound assisted synthesis of hybrid quinoline anchored with 4-R-benzenesulfonamide moiety with potential antimicrobial activity

Dumitrela Diaconu; Violeta Mangalagiu; Simona Dunca; Dorina Amariucai-Mantu; Vasilichia Antoci; Tiberiu Roman; Ionel I Mangalagiu

doi:10.1016/j.heliyon.2023.e21518

Ultrasound assisted synthesis of hybrid quinoline anchored with 4-R-benzenesulfonamide moiety with potential antimicrobial activity

Heliyon. 2023 Nov 3;9(11):e21518. doi: 10.1016/j.heliyon.2023.e21518. eCollection 2023 Nov.

Authors

Dumitrela Diaconu^{1

2}, Violeta Mangalagiu¹, Simona Dunca³, Dorina Amariucai-Mantu⁴, Vasilichia Antoci⁴, Tiberiu Roman¹, Ionel I Mangalagiu^{4

1}

Affiliations

¹ Alexandru Ioan Cuza University of Iasi, Institute of Interdisciplinary Research - CERNESIM Center, 11 Carol Bvd, 700506-Iasi, Romania.
² Alexandru Ioan Cuza University of Iasi, RECENT-AIR, 11 Carol Bvd, 700506-Iasi, Romania.
³ Alexandru Ioan Cuza University of Iasi, Faculty of Biology, 11 Carol Bvd, 700506-Iasi, Romania.
⁴ Alexandru Ioan Cuza University of Iasi, Faculty of Chemistry, 11 Carol Bvd, 700506-Iasi, Romania.

Abstract

We present in this paper a direct and efficient study regarding synthesis and spectral characterization of three series of hybrid quinoline anchored with 4-R-benzenesulfonamide moiety, with potential antimicrobial activity, by using ultrasound (US) irradiation and conventional methods (CV). The synthesis pathway is efficient and direct, in two steps: an initial N-acylation of 8-aminoquinoline followed by metal complexation with variously M²⁺ metals (Cd²⁺, Co²⁺, Cu²⁺, Ni²⁺, Pd²⁺, Zn²⁺). For both type of reactions, N-acylation and complexation, under US irradiations the synthesis have some undeniable advantages: the most relevant being the higher yields, a dramatically decrease for reaction time (with about 150 (one hundred fifty) folds for complexation) comparative with conventional methods (CV) (therefore the spent energy decrease in the same way), a decrease of the amount of used solvents. Taking into account the above considerations these reactions setup could be appreciated as eco-friendly. The structures of the obtained hybrid quinoline - sulfonamide complexes (HQBSM) were determined by elemental analysis and by using spectral investigations: FT-IR, NMR experiments, and X-ray diffraction (in three cases). The FT-IR and NMR spectra of complexes show a similar spectroscopic pattern for all complexes and fully confirm the proposed structures. The X-ray spectra analyses prove without doubts the structure of metal complexes, indicating that their structure depends essentially by two factors: the nature of metal and the nature of sulfonamide-quinoline moieties. Complexes containing 4-methoxy-benzoyl moiety and Zn²⁺ (e.g. 6a) are tetra-coordinated while in the Ni²⁺ complex (e.g. 6e) the metallic ion forms a distorted square-based bi-pyramid. In the complexes containing 4-nitro-benzoyl moiety and Cd²⁺ (e.g. 5d) the metallic ion forms a triangular bipyramid. The antibacterial and antifungal assay reveal that only hybrid HQBSM complex (4e) (with 4-chlorophenyl moiety and Ni²⁺ in molecule) have a significant antibacterial activity.

Keywords: Antibacterial activity; Environmentally friendly synthesis; Hybrid quinoline -benzenesulfonamide; Spectral characterization; Ultrasounds.