Biological Effects and Crystal X-Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies.

A novel Schiff base namely 3,5-di-tert-butyl-6-((2-(perfluorophenyl)hydrazono)methyl)phenol was successfully synthesized and characterized using FT-IR and 1 H-NMR, 13 C-NMR, and 19 F-NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X-ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti-bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF-7 and PC-3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 µM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti-bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound.

In vitro antifungal and antibiofilm activities of novel sulfonyl hydrazone derivatives against Candida spp.

BACKGROUND: The aim of this study was to investigate the antifungal and antibiofilm activity of the new sulfonyl hydrazones compound derived from sulphonamides. METHODS: In this study, new sulfonyl hydrazone series were synthesized via a green chemistry method. The structures of the synthesized compounds were characterized by elemental analyses and spectroscopic methods. The antifungal activities of the Anaf compounds against Candida strains under planktonic conditions were tested. The biofilm-forming ability of Candida strains was determined and the inhibitory effects of Anaf compounds on Candida biofilms compared with fluconazole were measured by MTT assay. Expression analysis of biofilm-related genes was investigated with qRT-PCR. The statistical analysis was performed using a one-way ANOVA test. CANDIDA: strains was determined and the inhibitory effects of Anaf compounds on Candida biofilms compared with fluconazole were measured by MTT assay. Expression analysis of biofilm-related genes was investigated with qRT-PCR. The statistical analysis was performed using a one-way ANOVA test. RESULTS: A total of 16 (45.7%) out of 35 Candida isolates were determined as strong biofilm producers in this study. C. albicans was the most biofilm producer, followed by C. krusei and C. lusitaniae. The Anaf compounds had a broad spectrum of activity with MIC values ranging from 4 µg/ml to 64 µg/ml. Our data indicated that the Anaf compound had a significant effect on inhibiting biofilm formation in both fluconazole-susceptible and -resistant strains. The expression levels of hypha-specific genes als3, hwp1, ece1 and sap5 were downregulated by Anaf compounds. CONCLUSIONS: Our study revealed that the Anaf compounds had antifungal activity and inhibited fungal biofilms, which may be related to the suppression of C. albicans adherence and hyphal formation. These results suggest that Anaf compounds may have therapeutic potential for the treatment and prevention of biofilm-associated Candida infections.

Cytotoxic effects, carbonic anhydrase isoenzymes, α-glycosidase and acetylcholinesterase inhibitory properties, and molecular docking studies of heteroatom-containing sulfonyl hydrazone derivatives.

Today, interest in studies on the search for new drugs to be used in diseases such as cancer, cardiovascular diseases, neurodegenerative diseases and diabetes, as well as prevention of microbial inflammation is increasing day by day. Emerging biological and pharmacological effects of sulfonyl hydrazone derivative compounds reveal their importance. In the present study, heteroatom-containing sulfonyl hydrazone derivatives have been studied for their anticancer and antimicrobial properties, as well as their effects on enzymes that could play roles in Alzheimer's dissease and diabetes. High doses of the tested compounds significantly decreased the cell viabilities of breast cancer (MCF-7) and prostate cancer (PC-3) cell lines. Furthermore, all compounds possessed antimicrobial activities against very common bacteria E. coli and S. aureus. These compounds were good inhibitors of the α-glycosidase, human carbonic anhydrase I and II isoforms and acetylcholinesterase enzyme with Ki values in the range of 1.14 ± 0.14-3.63 ± 0.26 nM for α-glycosidase, 66.05 ± 9.21-125.45 ± 11.54 nM for hCA I, 89.14 ± 10.43-170.22 ± 26.05 nM for hCA II and 754.03 ± 73.22-943.92 ± 58.15 nM for AChE, respectively. Molecular docking method was used to theoretically compare biological activities of sulfonyl hydrazone derivatives against enzymes. The theoretical results were compared with the experimental results. Thus, these compounds have strong biological activities.Communicated by Ramaswamy H. Sarma.

Synthesis, characterization and antibacterial activity of new sulfonyl hydrazone derivatives and their nickel(II) complexes.

Prophane sulfonic acid hydrazide (psh: CH(3)CH(2)CH(2)SO(2)NHNH(2)) derivatives as salicylaldehydeprophanesulfonylhydrazone (salpsh), 5-methylsalicylaldehydeprophanesulfonylhydrazone (5-msalpsh), 2-hydroxyacetophenoneprophanesulfonylhydrazone (afpsh), 5-methyl-2-hydroxyacetophenoneprophanesulfonylhydrazone (5-mafpsh) and their Ni(II) complexes have been synthesized. The structure of these compounds has been investigated by using elemental analysis, FTIR, (1)H NMR, LC/MS, UV-vis spectrophotometric method, magnetic susceptibility and conductivity measurements. The complexes were found to have general compositions [NiL2]. Square-planer structures are proposed for the Ni(II) complexes on the basis of magnetic evidence, electronic spectra and TGA data. Bacterial activities of sulfonyl hydrazone compounds were studied against gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis, Bacillus magaterium and gram-negative bacteria: Salmonella enteritidis, Escherichia coli by using minimum inhibitory concentrations (MICs) method.