Effective Microwave-Assisted Synthesis of 2-Chloro-5,6-dimethyl-3-(((substituted-benzylidene)hydrazono)methyl)-quinoline and Its Biological Assessment

• Published in: Russian journal of bioorganic chemistry 2024-02, Vol.50 (1), p.239-250
• Main Authors: Vegal, N. K., Bhatt, T. D., Kachhot, K., Joshi, H. S.
• Format: Article
• Language: English
• Subjects: Acetic acid; Anticancer properties; Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Chemical synthesis; Coliforms; Dilution; E coli; Fungicides; Gram-positive bacteria; Life Sciences; Organic Chemistry; Quinoline; Substitutes
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162024010254

ective: The quinoline scaffold is widely acknowledged as a critical framework for the development of novel pharmaceuticals. The derivatives of quinoline have antifungal, antibacterial, antitumor, and anticancer effects. Over the past 30 years, bacterial and fungal infections have grown significantly. Developing new infectious illness treatments is a major issue. As antimicrobials, we produced substituted 2-chloroquinoline compounds. The antimicrobial screening shows moderate activities against used microbes. Methods: By employing microwave irradiation, 2-chloro-5,6-dimethyl-3-(((substituted-benzylidene)hydrazono)methyl)quinoline can be synthesized quickly and efficiently. One-pot reaction between ( E )-2-chloro-3-(hydrazonomethyl)-7,8-dimethylquinoline and substituted Carbaldehyde in glacial acetic acid and MeOH as a solvent yields the anticipated outcome. Results and Discussion: The MIC of produced compounds was determined by broth dilution. All fifteen ( I–XV ) synthesized compounds were evaluated for their antibacterial and antifungal activity in vitro . Compounds ( I–VII ), ( X­–XIII ), and ( XIV ) have greater antibacterial activity against Staphylococcus aureus and Streptococcus pyogenes Gram-positive bacteria, Compounds ( IV ), ( VII ), ( XIII ), ( XIV ), and ( XV ) have demonstrated effective antibacterial activity against Escherichia coli and Pseudomonas aeruginosa Gram-negative bacteria. Compounds ( I ), ( IV ), ( V ), and ( XI ) exhibited moderate antifungal activity against C. albicans , A. niger , and A. clavatus . Conclusions: A powerful one-pot approach has been designed to synthesize substituted quinolones. Microwave-assisted synthesis greatly accelerates reaction rate and reduces product impurityand shows modest in vitro antimicrobial and antifungal activity.