Antimicrobial assesment of aroylhydrazone derivatives in vitro

Abstract

Aroylhydrazones 1–13 were screened for antimicrobial and antibiofilm activities in vitro. N′-(2-hydroxy-phenylmethylidene)-3-pyridinecarbohydrazide (2), N′-(5-chloro-2-hydroxyphenyl-methylidene)-3-pyridinecarbohydrazide (10), N′-(3,5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide (11), and N′-(2-hydroxy-5-nitrophenylmethylidene)-3-pyridinecarbohydrazide (12) showed antibacterial activity against Escherichia coli, with MIC values (in µmol mL−1) of 0.18–0.23, 0.11–0.20, 0.16–0.17 and 0.35–0.37, resp. Compounds 11 and 12, as well as N′-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide (6) and N′-(2-hydroxy-5- methoxyphenylmethylidene)-3-pyridinecarbohydrazide (8) showed antibacterial activity against Staphylococcus aureus, with the lowest MIC values of 0.005–0.2, 0.05–0.12, 0.06–0.48 and 0.17–0.99 µmol mL−1. N′-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide (7) showed antifungal activity against both fluconazole resistant and susceptible C. albicans strains with IC90 range of 0.18–0.1 µmol mL−1. Only compound 11 showed activity against C. albicans ATCC 10231 comparable to the activity of nystatin (the lowest MIC 4.0 ×10−2 vs. 1.7 × 10−2 µmol mL−1). Good activity regarding multi-resistant clinical strains was observed for compound 12 against MRSA strain (MIC 0.02 µmol mL−1) and compounds 2, 6 and 12 against ESBL+ E. coli MFBF 12794, with the lowest MIC for compound 12 (IC50 0.16 µmol mL−1). Anti-biofilm activity was found for compounds 2 (MBFIC 0.015–0.02 µmol mL−1 against MRSA) and 12 (MBFIC 0.013 µmol mL−1 against EBSL+ E. coli). In the case of compound 2 against MRSA biofilm formation, MBFIC values were comparable to those of gentamicin sulphate, whereas in the case of compound 12 and EBSL+ E. coli even more favourable activity compared to gentamicin was observed.

Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

“…Antibacterial assays performed in this study showed that compound 17 with nitro group displayed good inhibition of bacterial growth, whereas the compounds without an electron-withdrawing group (chloroand nitro-) showed weak antibacterial activity (Figure 11, Table 5). According to the authors, this may be due to the fact that electron-withdrawing substituents increase the lipophilicity of the compounds, which leads to higher partitioning of such compounds into the lipophilic phase of a microbial membrane [22]. 6, Figure 12) [23].…”

Investigation of 4-Hydrazinobenzoic Acid Derivatives for Their Antioxidant Activity: In Vitro Screening and DFT Study

“…Among them, hydrazine-, hydrazone-, and isothiocyanate-based compounds are found to have various applications in organic synthesis, medicinal chemistry, combinatorial chemistry, and supramolecular chemistry. − Concerning organic synthesis, such compounds were proved to participate in the construction of different heterocyclic scaffold classes such as azetidines, coumarins, oxadiazolines, diazoles, triazoles, quinazolines, thiazolidines benzothiazines, and triazoloquinazolines. − Their distinct biological significance was explained on the basis of the specific structural combination for a (−NH–NCH−) or (N–N) group with a carbonyl or thiocarbonyl group and their reactivities toward both electrophiles and nucleophiles. Therefore, they are present in many bioactive compounds and demonstrate a wide variety of biological activities including anticancer, antioxidant, antimicrobial, antifungal, anti-inflammatory, anticonvulsant, antiviral, and antiprotozoal effects. − The process of discovering antioxidants has been gaining growing interest due to their valuable protective roles in both pharmaceutical and food industries. In human physiology, they play an essential role against oxidative deterioration and oxidative stress-mediated mechanisms, whereas in the food system, antioxidants retard lipid peroxidation, prevent the formation of secondary lipid peroxidation products, maintain the flavor, color, and texture of the food product during storage, and reduce the interaction of lipid-derived carbonyls with proteins that is accompanied by alteration in protein function. , There has been renewed interest to explore new antioxidant molecules either synthetically or naturally, so as to utilize them as the main agents to counter toxicity mediated by radicals.…”