This work evaluates the
antioxidant and antidiabetic activities of two metformin hydrochloride-based Schiff bases. Moreover, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) ...assay was used to examine the
cytotoxic effects of HL1 and HL2 on the A549 lung cancer cell line. The two Schiff bases that have been previously synthesized by using two effective, green techniques, namely stirring and microwave-assisted, are
-dimethyl-
′-(
)-(2-nitrophenyl) methylidene imidodicarbonimidic diamide and
-dimethyl-
′-(
)-(4-nitrophenyl) methylidene imidodicarbonimidic diamide, indicated by HL1 and HL2, respectively. Studies of antidiabetic efficacy using alpha-amylase revealed that HL2 has a higher inhibition than HL1, but the results on sucrase enzyme showed that HL1 had the highest inhibitory action, whereas the outcome of the antioxidant test with the 2,2-diphenyl-1-picrylhydrazyl assay demonstrated that HL2 was the most effective antioxidant, followed by ascorbic acid and HL1. In the MTT assay, HL1 had the best result, with an IC
value of 57.13 µg/mL compared to HL2 with an IC
value of 76.83 µg/mL. It was observed that HL1 was the most effective against the human lung cancer cell line A459. The findings were supported by computational and pharmacokinetic studies (SwissADME). Based on empirical and computational studies, we suggest that HL1 and HL2 are promising candidates as antioxidants and antidiabetics after being examined
This study sought to assess the heavy metal content, phytochemical composition, antibacterial activity, and absorption, distribution, metabolism, and excretion (ADME) properties of
L. tree. The heavy ...metal content of the plant roots was determined using inductively coupled plasma-mass spectrometry technique, and it was found that only Cr, Mn, Fe, and Ni concentrations were above the permissible limits for edible plants. Gas chromatography-mass spectrometry analysis identified 11 phytochemicals in the aqueous extract of the plant. Both
and
confirmed the extract’s antibacterial efficacy. The aqueous extract showed significant antibacterial activity, with minimal inhibition concentration values of 125 µg/mL against
,
, and
. Among the 11 identified compounds, 1,8-Dioxa-5-thiaoctane,8-(9-borabicyclo3,3,1non-9-yl)-3-(9 borabicyclo3,3,1non-9-yloxy)-1-phenyl- showed the highest docking score (−8.31 kcal/mol) when docked into the active site of
MenB protein (PDB id: 3t88). It formed four hydrogen bonds with GLY86, GLY85, GLY132, and GLY133. Furthermore, the identified compounds were analyzed for ADME properties, most of them showed very good pharmacokinetic properties and did not violate Lipinski’s Rule of Five. Additional research is required to determine the medicinal potential of the compounds that have antibacterial activity.
The growing interest in exploring mushrooms and their bioactive components as potential therapies for diabetes and inflammatory conditions has prompted our investigation. In this study, we examined ...the methanolic extract, as well as the petroleum ether and ethyl acetate fractions, derived from the fruiting bodies of
and assessed the potential
anti-inflammatory and anti-diabetic effects. The inhibition of salivary α-amylase, salivary sucrase, and α-glucosidase enzymes by the methanolic extract and its fractions was used to measure the level of antidiabetic activity. Further, the inhibitory effects of the enzymes lipoxygenase (LOX), cyclooxygenase (COX), and myeloperoxidase (MPO) were tested to assess the anti-inflammatory efficacy of the methanolic extract and its fractions. The fraction containing ethyl acetate has been demonstrated to have the highest level of
antidiabetic effect, exhibiting IC
values of 44.93, 27.70, and 44.75 μg/ml for salivary α-amylase, salivary sucrase, and α-glucosidase enzymes, respectively. Moreover, the fraction of ethyl acetate revealed the greatest
anti-inflammatory action, with IC
values of 25.67 μg/ml for LOX, 34.04 μg/ml for COX, and 38.71 μg/ml for MPO.
Novel Schiff bases of metformin hydrochloride and (
)
-nitrobenzaldehyde were synthesized by employing two efficient environmentally friendly methods, namely, stirring and microwave-assisted methods ...using water as the solvent. The advantage of microwave irradiation over the other methods was represented in the reduction of reaction time and wastes, and good yields; however, water in both methods plays the role of eco-friendly solvent. The structural properties of the (
)
-isomer products were analyzed by elemental analysis, Fourier transform infrared (FTIR) spectroscopy, UV-Visible (UV-Vis) spectroscopy,
H nuclear magnetic resonance (NMR) spectroscopy,
C NMR spectroscopy, mass spectroscopy, and differential scanning calorimetry (DSC). The newly synthesized compounds were screened for their antibacterial activity against selected Gram-positive (ATCC 25923, ATCC 43300, and ATCC 29212) and Gram-negative (ATCC 25922, ATCC 27853, and ATCC 700603) bacteria using the agar well diffusion method. Compared with the standard drug streptomycin, both Schiff bases exhibited moderate bactericidal activity against the tested bacteria with higher values of
-nitro compared with the
-nitro isomer; however, no effect on ATCC 43300 and ATCC 27853 was observed under the experimental conditions employed.
A series of novel compounds, mono-5-isoxazolidines, and bis (5-isoxazolidines) derivatives, were prepared as bicycloadducts. The new series of isoxazolidines were designed and synthesized via ...1,3-dipolar cycloaddition reaction of nitrones with 3,9-Divinyl-2,4,8,10-tetra oxaspiro (5-5) undecane in the context of new antimicrobial and antioxidant drugs discovery and were fully characterized by FT-IR, 13C-NMR, and 1H-NMR spectroscopy. The physicochemical properties of all the novel cycloadducts, like bioactivity score and lipophilicity, were predicted using calculative methods. Similarly, the pharmacokinetic properties such as metabolism, absorption, distribution, and excretion (ADME) were also predicted. Most of the tested compounds exhibited antimicrobial properties to varying degrees against various bacterial species, including the Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli, and the Gram-positive bacteria Streptococcus pyogenus and Staphylococcus aureus, Antifungal properties were also observed against the tested fungi like Candida albicans, Aspergillus niger, and Aspergillus clavatus. The activity data exhibited that most compounds have high activity as compared to the standard drugs. In the range of graded doses, the results of some selected compounds revealed that some are high antioxidants while others are moderate or weak antioxidants. As evidenced by the molecular docking studies, the synthesized compounds showed good binding mode better than a standard drug, against the protein of a Pantothenate Synthetase enzyme (PDB-2X3F).
Isoxazolidines; Bicycloadducts; Nitrones; 1,3-Dipolar cycloaddition reaction.; Drug-likeness; Docking study.
In order to address the challenges associated with antibiotic resistance by bacteria, two new complexes, Ni(II) and Zn(II), have been synthesized using the conventional method based on Schiff base ...ligand (E)-2-((5-bromothiazol-2-yl) imino) methyl) phenol. The Schiff base ligand (HL) was synthesized using salicylaldehyde and 5-(4-bromophenyl)thiazol-2-amine in both traditional and efficient, ecologically friendly, microwave-assisted procedures. The ligand and its complexes were evaluated by elemental analyses, FTIR spectroscopy, UV-Vis spectroscopy, nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA) and magnetic susceptibility. The ligand and its complexes were tested for antibacterial activity against three Gram-positive bacteria (Staphylococcus aureus ATCC 25923, Methicillin-resistant Staphylococcus aureus ATCC 43300 and Enterococcus faecalis ATCC 29212) and three Gram-negative bacteria (Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922 and Klebsiella pneumoniae ATCC 700603). The findings demonstrate the potent activity of the ligand and its complexes against selective bacteria but the Ni(II) complex with MIC values ranging from 1.95 to 7.81 µg/mL outperformed all other compounds, including the widely used antibiotic Streptomycin. Furthermore, the docking study provided evidence supporting the validity of the antimicrobial results, since the Ni complex showed superior binding affinity against to E. coli NAD synthetase, which had a docking score (−7.61 kcal/mol).
(Z)-N′-(4-methoxybenzylidene)benzohydrazide (HL) and its Ni(II) complex (Ni(II)-2L) were synthesized using eco-friendly protocols. The single X-ray crystal structure of Ni(II)-2L was solved. ...Moreover, the structural properties were evaluated using Fourier transform infrared, proton nuclear magnetic resonance, mass, and Ultraviolet/Visible spectroscopy. The diamagnetic and thermal stability were assessed using magnetic susceptibility and thermogravimetric analysis, respectively. The biological activities of both HL and Ni(II)-2L (62.5–1000 μg/mL) against Gram-positive (Staphylococcus aureus and Streptococcus pyogenes) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacterial and fungal (Candida albicans, Aspergillus niger, and Aspergillus clavatus) species were studied using the minimum inhibitory concentration (MIC) tests method in reference to Gentamycin and Nystatin standard drugs, respectively. The results revealed an affordable, environmentally friendly, and efficient synthetic method of HL using water as a green solvent. The Ni(II)-2L complex crystallized in a distorted square planar, P21/n space group, and one Ni(II) to two bidentate negatively charged ligand ratio. The analysis of biological activity revealed higher activity of the complex against S. aureus and S. pyogenes (bacteria) and A. niger and A. clavatus (fungi) compared to the ligand. However, the highest activity was at a MIC of 62.5 μg/mL for the complex against S. pyogenes and for the ligand against E. coli. Therefore, both HL and Ni(II)-2L could be promising potential antimicrobials and their selective activity could be an additional benefit of these bioactive materials.
A comparative study of a Schiff base reaction involving benzaldehyde and n-butylamine was carried out to improve the yield of the resulting imine. This reaction was carried out at different ...temperatures without and with the elimination of the water produced during the process by the pervaporation (PV) technique using a typical cylindrical cell. To reach this goal, different dense membranes made of crosslinked poly(vinyl alcohol) with different oxalic acid (crosslinker) contents were prepared by the solvent casting method. Different parameters influencing the performance of the membrane in the separation process including swellability, diffusivity, crosslinking density, and thermal properties were investigated. The total and partial cumulative transmembranar fluxes as well as the separation factor were studied and the separation process was monitored by HPLC analysis. The n-butyl-1-phenylmethanimine produced was characterized by FTIR and 1HNMR analyses. The results obtained were a clear improvement in the yield of the reaction. For example, the yield obtained from the Schiff base reaction occurring without assistance by PV varied from 58 to 84 wt% when the temperature changed from 5 to 45 °C. On the other hand, when the PV process was used to eliminate water from this reaction mixture, the yield went from 90.4 to 98.6% by weight in this same temperature order. The cumulative total and partial fluxes significantly decreased with time. On the other hand, the separation factor reached a maximum at about one hour at 5, 15, and 45 °C. At 25 °C, the maximum total flux was reached at about 2 h of the PV process. The best selectivity of the PVA-0.5 membrane with regard to water was obtained at 15 °C. It was also revealed from the results obtained that the cumulative total and partial flux decreased rapidly with time and the separation factor reached a maximum at one hour into the PV process, in which 1.51 × 104 was reached at 15 °C, 6.25 × 103 and 3.50 × 103 at one hour of the separation process, and 10.23 × 103 at 25 °C at 2 h of the water removal by PV.
•Two novels open-chain–sugar nitrones were designed, synthesized, and isolated.•Novel biologically active N-Sugar-derived isoxazolidines derivatives have been synthesized, characterized.•The ...synthesized compounds were assessed for their antimicrobial activity using the disk diffusion method.•Characteristics druglikeness and pharmacokinetic have been predicted by ADMET predictive.•Molecular docking analysis and binding mode were carried out to examine the binding interactions of the most active analogues with the DNA gyrase enzyme (PDB id 1KZN).
Novel biologically active N-Sugar-derived isoxazolidines derivatives (2a, 2b, 3a, 3b) have been synthesized diastereospecifically by 1,3-dipolar cycloaddition reaction of nitrones (a, b) with maleimide and maleic acid. Nitrones were prepared in a pure form as chiral open-chain sugar-derived nitrones in an effort to explore a new type of antimicrobial agents. FTIR, 1H NMR, and 13C NMR spectrometric analysis characterized the structures of the compounds. The synthesized compounds were examined for their antimicrobial activity using the disk diffusion method against Gram-negative bacteria Escherichia coli; the Gram-positive bacteria staphylococcus aureus and against pathogenic fungi Candida albicans and Microsporum gypseum. Isoxazolidines (3a, 2a, 3b) proved to have strong antimicrobial activity compared to the standard drugs, as well as Drug-likeness and pharmacokinetic characteristics were predicted. Pharmacokinetic studies indicated that most derivatives exhibit acceptable predictive ADME properties and excellent fit with the Lipinski rules. Molecular docking was used to examine the binding interactions of the most active analogues with the active site of the DNA gyrase enzyme (PDB id 1KZN). Results showed that the enhanced activity of compounds (3a, 3b, 2a) exhibited stronger docking scores binding to the active site than the Nitrofurazone (standard drug). These findings suggest that analogues (3a, 3b) can be used as the best candidates for designing and discovering novel antimicrobial agents.
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•A new series of multisubstituted isoxazolidines was successfully synthesized by 1,3-dipolar cycloaddition and Zinc chloride was utilized as a catalyst.•Antimicrobial activities of the synthesized ...compounds were evaluated against various types of bacteria and fungi species.•The compounds also showed good antioxidant activity by in vitro assay.•The synthesized compounds followed Lipinski's rule of five, making them suitable for oral drug development.•Molecular docking studies further supported the in vitro antibacterial evaluation.
In the effort of our endeavour to synthesize new heterocyclic bioactive agents, we succeed the synthesis of a new series of Multisubstituted isoxazolidines (3-(4- substituted)-5-(1H-imidazol-1-yl)-2-methyl-1,2-oxazolidine derivatives (3a–l) by 1,3-dipolar cycloaddition between chiral nitrone (1a–l) and 1-vinylimidazole. The spectral data was utilized to verify and elucidate the structures and mechanistic routes of all the products. By utilizing zinc chloride as a catalyst, the reaction rate was significantly enhanced, resulting in a reduction of the reaction time by over 100-fold. After the synthesis process, our objective was to examine the effectiveness of the synthesized compounds as antimicrobial agents against a range of bacterial and fungal species. The antimicrobial properties of the compounds were assessed using the macro double broth dilution method. with some exhibiting higher potency than established antibiotics and antifungals. Additionally, the compounds exhibited good antioxidant activity by in vitro assay, with 3c, 3g, and 3l showing higher activity than ascorbic acid. The study also evaluated the drug-likeness of the synthesized compounds and found that they followed Lipinski's rule of five, making them suitable for oral drug development. Molecular docking studies further supported the in vitro antibacterial evaluation The synthesized compounds demonstrated an excellent binding mode with the target 1QFG protein, some outperformed a standard drug.
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