Synthesis, antibacterial and anticancer activity, and docking study of aminoguanidines containing an alkynyl moiety

Abstract

Two series of aminoguanidines containing an alkynyl moiety were designed, synthesised, and screened for antibacterial and anticancer activities. Generally, the series 3a-3j with a 1,2-diphenylethyne exhibited better antibacterial activity than the other series (6a-6k) holding 1,4-diphenylbuta-1,3-diyne moiety antibacterial activity. Most compounds in series 3a-3j showed potent growth inhibition against the tested bacterial strains, with minimum inhibitory concentration (MIC) values in the range 0.25-8 mg/mL. Compound 3g demonstrated rapid and persistent bactericidal activity at 2 Â MIC. The resistance study revealed that resistance of the tested bacteria towards 3g is not easily developed. Molecular docking studies revealed that compounds 3g and 6e bind strongly to the LpxC and FabH enzymes. Moreover, excellent activity of selected compounds against the growth of cancer cell lines A549 and SGC7901 was also observed, with IC 50 values in the range 0.30-4.57 mg/mL. These findings indicate that compounds containing the aminoguanidine moiety are promising candidates for the development of new antibacterial and anticancer agents.

N,2,6-Trisubstituted 1H-benzimidazole derivatives as a new scaffold of antimicrobial and anticancer agents: design, synthesis, in vitro evaluation, and in silico studies

“…The dual-acting anticancer and antimicrobial chemotherapy agents have been published in many studies. 4,[43][44][45][46] Moreover, people with cancer may have a higher risk of infection due to changes in the immune system that controls their body's defenses. 47 Therefore, our potential derivatives have shown to be promising agents in the development of dual therapeutic effects.…”

Semisynthesis and anti-cancer properties of novel honokiol derivatives in human nasopharyngeal carcinoma CNE-2Z cells

“…metformin) have been the focus of many studies because of their diverse pharmacolgical properties, including anti-cancer, anti-microbial, and anti-inflammatory effects. 32–35 In the present study, we modified the phenolic hydroxyl group of HNK and preserved the aminoguanidine moiety to obtain a series of novel HNK derivatives, and investigated the anti-NPC effects of these compounds in vitro and in vivo.…”

Development of Dicationic Bisguanidine-Arylfuran Derivatives as Potent Agents against Gram-Negative Bacteria

“…However, its activity against E. coli and other pathogenic Gram-negative bacteria from the ESKAPE group, commonly causing serious infections around the world and exhibiting troublesome antibiotic resistance patterns, has not previously been examined. A variety of antimicrobial guanidine-containing compounds have been reported [ 3 ], targeting the bacterial envelope [ 12 , 13 , 14 ] or key bacterial proteins, such as DNA gyrase [ 15 ], lipid A and fatty acid biosynthesis enzymes [ 16 ], the bacterial cell division protein FtsZ4 [ 17 ], the NorA efflux pump [ 18 ], or targeting the ribosomal decoding rRNA site [ 19 ].…”