Antimicrobial, anticancer activities, molecular docking, and DFT/B3LYP/LANL2DZ analysis of heterocyclic cellulose derivative and their Cu-complexes.

In this study, novel Cu-complexes of heterocyclic cellulose which were synthesized via the reaction of carboxymethyl cellulose (CMC) from bagasse pulp with NH2NH2 to give hydrazide cellulose which easily reacted with CS2 to form salt and then cyclized in the presence of HCl to afford cellulose oxadiazole, or with hydrazine hydrate to give cellulose triazole. Furthermore, the cellulose oxadiazole and triazole moieties acting as chelating agents with metal ion Cu (II), and all synthesized compounds were examined for their spectral analysis to show the adsorption of Cu (II) on the surface of cellulose through intramolecular hydrogen bonding. Results illustrated that cellulose oxadiazole and Cu- cellulose oxadiazole exhibited antimicrobial activities more than triazole and Cu- cellulose triazole. Furthermore, anticancer results showed that both cellulose oxadiazole and triazole exhibited activity higher than Cu-cellulose oxadiazole and Cu-cellulose triazole, where the cellulose triazole showed the highest activity (IC50 = 58.7 µg/µL). Additionally, the docking simulation of the synthesized cellulose complexes with different proteins such as PDBID:3t88, PDBID:4ynt, PDBID:1tgh, PDBID:2wje, and PDBID:4hdq and shortage bond length to confirm the experimental results. Optimization of metal complexes utilized the DFT/B3LYP/LANL2DZ basis set to confirm the stability of these metals theoretically and their physical descriptors and FMO analysis.

Antioxidant-rich brilliant polymeric nanocomposites for quick and efficient non-enzymatic hydrogen peroxide sensor.

In our current research, a new type of functional nanocomposites known as poly(methyl methacrylate/N,N-dimethyl aminoethylmethacrylate/(E)-2-cyano-N-cyclohexyl-3 (dimethylamino) acrylamide) [poly(MMA/DMAEMA/CHAA)] has been developed. These nanocomposites were created using microemulsion polymerization in conjunction with synthesized titanium dioxide (TiO2), and vanadium pentoxide (V2O5) nanoparticles. To understand the physio-chemical characteristics of the poly(MMA/DMAEMA/CHAA) and the metal oxide nanoparticles (MOs) integrated within them, various analytical techniques were employed. These techniques included Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR), X-ray diffraction analysis (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), and electrical approaches such as cyclic voltammetry (CV) and electrical impedance spectra (EIS). Based on the TEM results, nanospheres with a well-defined structure were developed for both the pure polymer and its composite with sizes ranging from 45 to 75 nm. All the TiO2 and V2O5-based nanocomposites showed significantly enhanced electrical attributes, with capacitance values surpassing those of the poly(MMA/DMAEMA/CHAA) nanosphere assemblies by a considerable margin. As a result, both direct electron transfer and direct hydrogen peroxide identification were evaluated for the nanocomposites. The amperometry results demonstrated a lower detection limit of 0.0085 µM and a rapid linear sensitivity in the range of 1 to 800 µM. The greatly improved electrolytic qualities of these nanocomposites make them suitable for various applications in fields such as battery storage, sensors, and biosensors.

Novel pyrazole and imidazolone compounds: synthesis, X-ray crystal structure with theoretical investigation of new pyrazole and imidazolone compounds anticipated insecticide's activities against targeting Plodia interpunctella and nilaparvata lugens.

In this study, we synthesized (2-propoxyphenyl)(3-(p-tolyl)oxiran-2-yl)methanone through oxidizing the double bond of the respective chalcone via the Weitz-Scheffer epoxidation reaction. Additionally, the chalcone with an oxirane ring served as a fundamental building block for the synthesis of various pyrazole and imidazole derivatives, employing diverse nitrogen nucleophiles. All synthesized compounds were confirmed via analytical and spectroscopic analysis, such as FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. Furthermore, all these nitrogen heterocycles were optimized via the DFT/B3LYP/6-31G(d,p) basis set and their physical descriptors were identified. Compound 11 was further confirmed using single-crystal X-ray diffraction with Hirshfeld analysis, and the results were correlated with the optimized structure by comparing their bond length and bond angle, which provided excellent correlation. Additionally, the insecticidal activities of the newly synthesized compounds were tested against P. interpunctella and Nilaparvata lugens. The heterocyclic compounds exhibited remarkable activity compared to the standard reference thiamethoxam. These findings were further confirmed through docking simulation with different proteins, namely PDBID 3aqy and 3wyw. The compounds interacted effectively within the protein pockets, displaying a higher binding energy with amino acids.

Designing a green poly(ß-amino ester) for the delivery of nicotinamide drugs with biological activities and conducting a DFT investigation.

The environmentally friendly polymerization process was carried out using microwave irradiation without additional solvents or catalysts to produce poly(ß-amino ester) (PßAE) which served as a drug delivery system. PßAE was synthesized through Michael addition polymerization of 1,4-butane diol diacrylate and piperazine. Swelling and biodegradation studies were conducted in various solvents and phosphate-buffered saline (PBS, pH 7.4) at 37 °C to evaluate the properties of the polymeric gel. The PßAE matrix demonstrated solubility enhancement for hydrophobic antimicrobial and antitumor-active nicotinamide derivatives (TEINH, APTAT, and MOAPM), controlling their release over 10 days in (PBS). The successful formation of free and loaded PßAE with nicotinamide active materials was confirmed by spectroscopic analysis including Fourier-transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). Optimization and physical descriptor determination via the DFT/B3LYP-631(G) basis set were performed to aid in the biological evaluation of these compounds with elucidation of their physical and chemical interaction between poly(ß-amino ester) and nicotinamide drugs.

Anti-proliferative activity, molecular genetics, docking analysis, and computational calculations of uracil cellulosic aldehyde derivatives.

In this study, the oxidation of microcrystalline cellulose using NaIO4 to yield the corresponding cellulose aldehyde utilized microwave irradiation as a green tool, the obtained cellulosic aldehyde was confirmed through spectral analysis and it has an active site to react with the synthesized uracil acetamide to afford the corresponding arylidene cellulosic MDAU(4), the latter compound which can easily due to presence of active CH=group behind a cyano group react with nitrogen nucleophile's and cyclized with hydrazine hydrate to give pyrazole cellulosic MDPA(5). The spectral analysis of the obtained cellulosic derivatives was confirmed with FT-IR, NMR, and SEM. Additionally, a neutral red uptake analysis has been used to investigate the cytotoxic activity of the cellulosic compounds MDAC(2), MDAU(4), and MDAP(5) against the cancer cells A549 and Caco2. After 48 h, Compound MDAU(4) had a stronger inhibitory effect on the growth of A549 and Caco2, compared to standard values. Then, using QRT-PCR, the appearance sites of the genes -Catenin, c-Myc, Cyclin D1, and MMP7 in A549 cells were examined. By reducing the expression levels of the Wnt signaling cascade genes -Catenin, c-Myc, Cyclin D1, and MMP7 when administered to A549 cells, compound MDAU(4) was shown in this investigation to be a viable candidate compared to lung cancer. Additionally, docking simulation was used to explore the uracil cellulosic heterocycles attached to different proteins, and computational investigations of these compounds looked at how well their physical characteristics matched the outcomes of their experiments.

Synthesis, reactions and application of chalcones: a systematic review.

Chalcones are a group of naturally occurring compounds that have biological effects that include anti-inflammatory, anti-cancer, and antibacterial properties. Current chalcone research, including their synthesis, structure-activity relationships, and biological activities, is summarized herein. Along with their toxicity and safety profiles, the prospective usage of chalcones in medicinal research and development is discussed. This review emphasizes the need for additional research in order to fully examine the therapeutic potential of chalcones as therapeutic agents for the treatment of a variety of disorders.

Making a new bromo-containing cellulosic dye with antibacterial properties for use on various fabrics using computational research.

The reaction of cyanoethyl cellulose with para-bromo diazonium chloride resulted in the creation of a novel bromo-containing cellulosic (MCPT). The dispersion stability of MCPT has been improved by its dispersion into 1% waterborne polyurethane acrylate (WPUA). TEM, particle size, and zeta potential were used to track the dispersion stability of aqueous MCPT and MCPT in 1% WPUA and particle size. The prepared MCPT has been utilized as a unique green colorant (dye) for the printing of cotton, polyester, and cotton/polyester blend fabrics using a silkscreen printing technique through a single printing step and one color system. Color improvement has been achieved by printing different fabrics with a printing paste of MCPT dispersed in 1% WPUA. The MCPT and MCPT in 1% WPUA printed fabrics were evaluated for rubbing, light, washing, and perspiration fastness, UV blocking activity, and antibacterial activity. These findings were established through structural optimization at the DFT/B3LYP/6-31 (G) level and simulations involving several proteins.

Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation.

Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers. These substances have the ability to engage covalently or non-covalently with particular residues in the target proteins, inhibiting them. In this study, the formation of N-, S-, and O-containing heterocycles by the interaction of chalcone with nitrogen-containing nucleophiles such as hydrazine, hydroxyl amine, guanidine, urea, and aminothiourea was explored. FT-IR, UV-visible, NMR, and mass spectrometric studies were used to confirm the heterocyclic compounds that were produced. These substances were tested for their antioxidant activity by their capacity to scavenge the artificial radicals 2,2-diphenyl-1-picrylhydrazyl (DPPH). The strongest antioxidant activity was demonstrated by compound 3 (IC50 = 93.4 µM), whereas compound 8 (IC50 = 448.70 µM) had the lowest activity when compared to vitamin C (IC50 141.9 µM). Also, the experimental findings and the docking estimation of these heterocyclic compounds with PDBID:3RP8 were in agreement. Additionally, the compounds' global reactivity characteristics, such as HOMO-LUMO gaps, electronic hardness, chemical potential, electrophilicity index, and Mulliken charges, were identified using DFT/B3LYP/6-31G(d,p) basis sets. The two chemicals that displayed the best antioxidant activity also had their molecular electrostatic potential (MEP) ascertained using DFT simulations.

Microwave-assisted synthesis, antioxidant activity, docking simulation, and DFT analysis of different heterocyclic compounds.

In this investigation, pressure microwave irradiation was used to clarify the activity of 1-(2-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one (3) towards several active methylene derivatives utilized the pressurized microwave irradiation as green energy resource . Chalcone 3 was allowed to react with ethyl cyanoacetate, acetylacetone, and thioglycolic acid; respectively, at 70 °C with pressure under microwave reaction condition to afford the corresponding 2-hydroxyphenylcyanopyridone, 2-hydroxyphenyl acetylcyclohexanone, and thieno[2,3-c]chromen-4-one derivatives respectively. Moreover, the reaction of chalcone 3 with hydrogen peroxide with stirring affords the corresponding chromen-4-one derivative. All the synthesized compounds were confirmed through spectral tools such as FT-IR, 1HNMR, 13CNMR, and mass spectrum. Furthermore, the synthesized heterocycles were exhibited excellent antioxidant activity and comparable with vitamin C, where the presence of the OH group increases the scavenger radical inhibition. Furthermore, the biological activity of compound 12 was demonstrated through molecular docking stimulation using two proteins, PDBID: 1DH2 and PDBID: 3RP8, which showed that compound 12 possesses greater binding energy and a shorter bond length comparable with ascorbic acid. Also, the compounds were optimized through DFT/B3LYP/6-31G (d,p) basis set and identification of their physical descriptors, whereas the compound 12 was confirmed through X-Ray single structure with Hirsh field analysis of the compound to know the hydrogen electrostatic bond interaction, and correlated with the optimized structure by comparing their bond length, bond angle, FT-IR, and NMR, which gave excellent correlation.

Anti-proliferative action, molecular investigation and computational studies of novel fused heterocyclic cellulosic compounds on human cancer cells.

Reactivity of MCEC (3) with diazonium chloride, DMF-DMA and NH2NH2 to afford fused heterocyclic cellulosic derivative which confirmed through spectral analysis. Also, the cellulosic compounds were evaluated their growth inhibitory activity contra cancer cells A549 and Caco2 using neutral red uptake assay. Compounds, MCEN(6), MCPT(5a), MCPT(5b) showed better growth inhibitory activity on A549 and Caco2 growth compared to control values. While compound MCPY(7) exerted the best cytotoxic activity against A549 cells after 48 h. The expression levels of HIF-1α, ß-Catenin, MYC, Cyclin D1 and MMP7 genes in A549 cells were examined using QRT-PCR. The compounds MCEN(6) and MCPY(7) down regulated levels of ß-Catenin, MYC, Cyclin D1 and MMP7 genes and up-regulated levels of HIF-1α when treated with A549 cells compared to control values. Also, these biological studies confirmed through docking stimulation with different proteins and showed least binding energy with amino acids and attached with NH2 and OH of cellulose with hydrogen bond interaction. Moreover, optimization of compounds using DFT/6-311(G) showed the stability of them and identifies their physical descriptors which showed excellent correlation with experimental results. Noteworthy, compounds, MCEN(6) and MCPY(7) were most promising anticancer agents against lung cancer through the regulation of apoptosis, cell cycle, proliferation, progression, chemo-resistance, and angiogenesis.

Synthesis of novel d-α-galactopyranosyl-l-seryl/l-threonyl-l-alanyl-l-alanine as useful precursors of new glycopeptide antibiotics with computational calculations studies.

New, simple, synthetic routes for the preparation of novel glycopeptide antibiotics are described. The structures of the synthesized compounds are elucidated by IR, two-dimensional NMR spectroscopy, and mass spectrometry. The stability of the new glycopeptide derivatives 10a,b is confirmed by assessing the physical character, HOMO-LUMO gap energy, ESP, and the corresponding correlation of 2D-NMR analysis. Furtherly, the target precursors are investigated via the DFT/B3LYP/6-311(G) basis set.

Synthesis, antimicrobial activities, docking studies and computational calculations of new bis-1,4-phenylene -1H-1,2,3-triazole derivatives utilized ultrasonic energy.

In this elucidation, we studied the utility of condensation reaction between 1,4-phenylenediamine (1) with acetyl acetone (2) with hydrazine hydrate utilized ultrasonic energy in one step reaction to afford the corresponding 1,1'-(1,4-phenylenebis (5-methyl-1H-1,2,3-triazole-1,4-diyl))bis(ethan-1-one) (4) in excellent yield. The ethanol solution of bis triazole (4) and different aldehyde derivatives were sonicated at 75 °C for 2 h to afford chalcone derivatives 5a-d which were confirmed via spectral data such as FTIR, 1HNMR, 13CNMR and mass spectra. Moreover, the intermolecular cyclization of chalcone (5a) with NH2NH2 in sodium hydroxide solution to give the corresponding 4,5-dihydro-1H-pyrazol-5-yl)-1H-indole (6) using ultrasonic energy for 4 h, while the Michael addition of chalcones (5a) and (5 b) with thiourea in basic condition to afford the corresponding pyrimidine-2-thiol derivatives (7) and (9). Treatment of compound (7) with NH2NH2 to afford 1,4-bis(4-(2-hydrazineyl-6-(1H-indol-3-yl)pyrimidin-4-yl) derivatives (8). The synthesized compounds were screened against various microbial strains and displayed excellent antimicrobial potential. Additionally, the docking studies of these nine compounds were carried out with (PDB ID:3t88), (PDB ID:2wje), (PDB ID:4ynt) and (PDB ID:1tgh) which were attached with different amino acids with shortage bond length, and it was noticed that PMTS1, PMTS2 and PMTS3 were the most stable compounds with the lowest energy affinity which is compatible with biological study. Furthermore, the theoretical investigation of bis-triazole compounds were optimized via DFT/B3LYP/6-31G(d) level which showed the hyperconjugation of nitrogen atoms and elucidated their physical parameters and NBO charges and confirmed their stability and biological activity.Communicated by Ramaswamy H. Sarma.

Synthesis, antimicrobial, anti-proliferative activities, molecular docking and DFT studies of novel pyrazolo[5,1-c][1, 2, 4]triazine-3-carboxamide derivatives.

In this investigation, we studied the reactivity of 5-aminouracil (1) with ethyl cyanoacetate (2) utilizing microwave irradiation to afford the corresponding 2-cyano-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide (3) in excellent yield. The electrophilic azo-coupling reaction of acetamide 3 with aromatic diazonium salts afforded the corresponding hydrazone derivatives 4a-d. The Michael addition cyclization of hydrazone in pyridine to give pyrazolo[5,1-c][1, 2, 4]triazine-3-carboxamide 5a-d derivatives. The obtained compounds were elucidated against antimicrobial activity and antitumor activity breast cancer cells (MCF-7) and liver cancer cells (HepG2) utilized MTT assay. Compounds 5b, 5c and 5d revealed more inhibitory influence on MCF7 and HepG2 growth than the reference drug doxorubicin (Dox) after 48 h incubation. Furthermore, molecular docking studies were carried out on one of the most effective compound 4-amino-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-7-(4-fluorophenyl) pyrazole [5,1-c][1, 2, 4]triazine-3-carboxamide (5c) (TFC) with (PDB: 3t88), (PDB: 2wje) , (PDB: 4ynt), (PDB: 1tgh), (PDB: 4hdq) and (PDB: 3pxe) which attached with different proteins with different energies and shortage bond distance. Also; the comprehensive theoretical and experimental mechanical studies of compound TFC and TMC were compatible with FTIR and 1H NMR spectral data. The optimized molecular structure of TFC with FTIR was examined via DFT/ B3LYP/6-31G (d) level.Communicated by Ramaswamy H. Sarma.

Electrochemical Detection of Endosulfan Using an AONP-PANI-SWCNT Modified Glassy Carbon Electrode.

This report narrates the successful application of a fabricated novel sensor for the trace detection of endosulfan (EDS). The sensor was made by modifying a glassy-carbon electrode (GCE) with polyaniline (PANI), chemically synthesized antimony oxide nanoparticles (AONPs), acid-functionalized, single-walled carbon nanotubes (fSWCNTs), and finally, the AONP-PANI-SWCNT nanocomposite. The electrochemical properties of the modified electrodes regarding endosulfan detection were investigated via cyclic voltammetry (CV) and square-wave voltammetry. The current response of the electrodes to EDS followed the trend GCE-AONP-PANI-SWCNT (-510 µA) > GCE-PANI (-59 µA) > GCE-AONPs (-11.4 µA) > GCE (-5.52 µA) > GCE-fSWCNTs (-0.168 µA). The obtained results indicated that the current response obtained at the AONP-PANI-SWCNT/GCE was higher with relatively low overpotential compared to those from the other electrodes investigated. This demonstrated the superiority of the AONP-PANI-SWCNT-modified GCE. The AONP-PANI-SWCNT/GCE demonstrated good electrocatalytic activities for the electrochemical reduction of EDS. The results obtained in this study are comparable with those in other reports. The sensitivity, limit of detection (LoD), and limit of quantification (LoQ) of AONP-PANI-SWCNT/GCE towards EDS was estimated to be 0.0623 µA/µM, 6.8 µM, and 20.6 µM, respectively. Selectivity, as well as the practical application of the fabricated sensor, were explored, and the results indicated that the EDS-reduction current was reduced by only 2.0% when interfering species were present, whilst average recoveries of EDS in real samples were above 97%.

Theoretical investigation on hydrogen bond interaction between adrenaline and hydrogen sulfide.

In this study, we elucidated the formation of hydrogen bond between adrenaline (AD) and hydrogen sulfide utilizing computational studies. Six potential complexes were studied including geometrical parameters, energy, vibrational frequency, topological analysis, natural bond orbital (NBO), quantum theory of atoms in molecules (QTAIM), and NMR analysis. Moreover, these calculations were examined through DFT/ωB97XD/6-311G++(d,p) level. It was found that there are no indication on formation on hydrogen bonding between the two catecholic OHs where the one formed between the amino group and the hydroxyl oxygen atom of adrenaline monomer was broken in AS1 to form two new interactions namely SH...N and O1H1...S, while it retained in other complexes. Furthermore, the bond became stronger due to cooperativity in AS3 and AS6, for the presence of withdrawing effect of the phenyl ring, the H-bonds formed with the side chain oxygen atom. The adrenaline and H2S interaction was experimentally examined via FT-IR spectrometry and thin layer chromatography for confirmation of our theoretical study. Graphical abstract.

Synthesis, Antitumor Activity, Molecular Docking and DFT Study of Novel Pyrimidiopyrazole Derivatives.

BACKGROUND: In this investigation, 2-cyano-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl) acetamide (3) reacts with dimethylformamide dimethyl acetal (DMF-DMA) to afford the corresponding (E)- 2-cyano-3-(dimethylamino)-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylam-ide (4) utilizing microwave irradiation. The condensation reactions of acrylamide derivative 4 with hydrazine derivatives obtain pyrazole derivatives 6a and 6b; respectively. The synthesized compounds demonstrate in vitro antitumor activity against liver tumor cell line HepG2. Furthermore, additional studies were carried out on the most effective compound 6b to evaluate the potential interaction against 4hdq synthase complex with ΔE= -4.5Kcal/mol and with short distance = 1.727Å and 2.027Å, respectively. The comprehensive theoretical studies of compounds 6a and 6b is based on bond length, bond angles and energy gap HOMO-LUMO. In addition, the vibrational frequencies of optimized compounds 6a and 6b were examined through DFT/B3LYP/6+31G(d) basis set. METHODS: In this research, synthesis of novel pyrimidiopyrazole derivatives calculated the computational studies to find suitable drug-receptor interactions and biological activity. RESULTS AND DISCUSSION: The synthesized pyrimidiopyrazole derivative 6b exhibited high antitumor activity IC50 =12.6 µg/ml and interacted it with 4hdq synthase complex with ΔE=-4.5Kcal/mol and with short distance = 1.727Å and 2.027Å. Furthermore, the optimized compounds utilize Gaussian 09W. CONCLUSION: In the optimized pyrimidiopyrazole derivatives, 6b showed better antitumor activity HeG-2 against 5-flurouracil due to its energy and confirmed more potent of hydrogen bond interaction with protein pocket.

Synthesis, anti-proliferative activity, computational studies of tetrazole cellulose utilizing different homogenous catalyst.

Micheal addition reaction of the microcrystalline cellulose (MCC) (1) with acrylonitrile (2) afford the corresponding microcrystalline cyanoethyl cellulose (MCEC) which cyclized via [2+3] cycloaddition reaction to afford the corresponding microcrystalline tetrazole cellulose (MCTC) with a different homogenous catalyst. The desired products were confirmed through the spectral data, FT-IR, 1HNMR, 13CNMR and also scanning electron microscope with different pore sizes. All MCTC exhibited excellent in vitro antitumor activity against hepatic and breast tumor cell such as HCT-116, HeG2, and MDA-MB-231; respectively. Additionally, the molecular docking of most effective compounds MCTC to evaluate its potential interaction against doxorubicin drug-binding protein (PDBID: 5OM5) and Crystal structure of Cu (I) CusA (PDBID: 3K0I). The computational calculation of optimized monomer (mCTC) to elucidate HOMO-LUMO gap, ESP and the vibrational frequencies was studied through DFT/ B3LYP/6-31G(d) and HF/6-31G(d) basis sets.