ABSTRACT
[This retracts the article DOI: 10.3762/bjoc.11.141.].
ABSTRACT
A novel series of acridine linked to thioacetamides 9a-o were synthesized and evaluated for their α-glucosidase inhibitory and cytotoxic activities. All the synthesized compounds exhibited excellent α-glucosidase inhibitory activity in the range of IC50â¯=â¯80.0⯱â¯2.0-383.1⯱â¯2.0⯵M against yeast α-glucosidase, when compared to the standard drug acarbose (IC50â¯=â¯750.0⯱â¯1.5⯵M). Among the synthesized compounds, 2-((6-chloro-2-methoxyacridin-9-yl)thio)-N-(p-tolyl) acetamide 9b displayed the highest α-glucosidase inhibitory activity (IC50â¯=â¯80.0⯱â¯2.0⯵M). The in vitro cytotoxic assay of compounds 9a-o against MCF-7 cell line revealed that only the compounds 9d, 9c, and 9n exhibited cytotoxic activity. Cytotoxic compounds 9d, 9c, and 9n did not show cytotoxic activity against the normal human cell lines HDF. Kinetic study revealed that the most potent compound 9b is a competitive inhibitor with a Ki of 85⯵M. Furthermore, the interaction modes of the most potent compounds 9b and 9f with α-glucosidase were evaluated through the molecular docking studies.
Subject(s)
Diabetes Mellitus, Type 2/drug therapy , Drug Design , Glycoside Hydrolase Inhibitors/chemical synthesis , Thioacetamide/chemistry , alpha-Glucosidases/metabolism , Acridines/chemistry , Binding Sites , Catalytic Domain , Cell Line , Cell Survival/drug effects , Diabetes Mellitus, Type 2/metabolism , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/therapeutic use , Humans , Hypoglycemic Agents/chemical synthesis , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/therapeutic use , Kinetics , Molecular Docking Simulation , Structure-Activity Relationship , Thioacetamide/pharmacology , Thioacetamide/therapeutic use , alpha-Glucosidases/chemistryABSTRACT
A novel multiwalled carbon nanotube catalyst with -SO3H functional groups was easily prepared from its starting materials and used as an efficient heterogeneous catalyst for one-pot Knoevenagel condensation, Michael addition, and cyclodehydration of 5,5-dimethyl-1,3-cyclohexanedione (dimedone) with various aromatic aldehydes. Using this method 1,8-dioxo-octahydroxanthenes were obtained in excellent yields at room temperature. The present method is superior in terms of reaction temperature, reaction time, easy work-up, high yields, and ease of recovery of catalyst.
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A stable and efficient phosphorus-free, low Pd-loading heterogeneous nanocatalyst comprising palladium and a multi-walled carbon nanotube was prepared and characterized by various techniques such as SEM, TEM, AFM, FT-IR, and Raman spectrometry, N2 adsorption isotherm and thermogravimetric analysis. This catalyst was used for the deprotection of phenol ethers. The catalyst selectivity for deprotection of between propargyl, allyl, and benzyl, as a protecting group, was studied. Also, the presence of different functional groups was studied to establish the scope and limitations of this method. The catalytic activity of recycled catalyst was evaluated. The results indicated that the catalyst is heterogeneous, stable, and very active under the established conditions, and it could be reused up to five times without any significant leaching. In addition, according to ICP analysis, low leaves of leaching of palladium from the catalyst was observed, which indicates that anthraquinone has an excellent ability to coordinate with palladium.
Subject(s)
Alkynes/chemistry , Ethers/chemistry , Nanotubes, Carbon/chemistry , Palladium/chemistry , Phenols/chemistry , Adsorption , CatalysisABSTRACT
An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.
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Objectives: In holistic medicine, developing personalized treatment plans is challenging due to the multitude of possible therapy combinations. This study introduces the use of a statistical approach to identify the most effective herbal medicines prescribed in Persian medicine (PM) in a small-scale sample of patients with type 2 diabetes mellitus (T2DM). Methods: This prospective observational cohort study was conducted with 47 patients with T2DM referred to Behesht Clinic in Tehran, Iran. A physician prescribed individualized PM treatment for T2DM and related systemic issues. The fasting blood sugar (FBS) level of each patient was recorded at initial and two follow-up visits, with visit intervals and treatment modifications determined by patient health status. Patients who completed two follow-up visits were included in the final analysis (n = 27). Data were analyzed using R software. A general linear model was assumed for the mean response, along with an exponential covariance pattern model, to manage irregularly timed measurements. Results: Two fitted models showed that, after adjusting for confounders, the use of the "Diabetes Capsule" significantly reduced the average FBS by 17.14 mmol/L (p = 0.046). For each unit increase in the consumption of "Diabetes Capsule" or "Hab-e-Amber Momiai," the average FBS decreased by 15.22 mmol/L (p = 0.015) and 14.14 mmol/L (p = 0.047), respectively. Conclusion: It is possible to observe which medications are most effective, even when treatments are applied in a holistic and personalized fashion. Preliminary studies such as these may identify promising products for testing in clinical trials conducted under standardized conditions, to inform initial choices for future personalized treatments.
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The efficient synthesis of chromeno[3,4-[Formula: see text]]quinoline derivatives by condensation of O-propargylated salicylaldehyde, or corresponding compounds and primary aromatic amine derivatives using a catalytic amount of heterogeneous Cu(II)BHPPDAH complex without being immobilized on any supports (5.0 mol%) in PEG 300 as a "green" solvent is described. The remarkable features of this protocol are good to high yields in all cases, short reaction times, a cleaner reaction profile in an environmentally benign solvent (PEG 300), and the method is applicable to large-scale operation without any problem. Furthermore, the catalyst was quantitatively recovered from the reaction mixture by simple filtration and reused at least seven times with almost consistent activity.
Subject(s)
Copper/chemistry , Polyethylene Glycols/chemistry , Quinolines/chemical synthesis , Catalysis , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Quinolines/chemistry , SolventsABSTRACT
A high-sensitivity flexible field-effect transistor (FET) based glucose sensor is fabricated that can surpass the conventional electrochemical glucometers in terms of sensitivity, limit of detection, and other performance parameters. The proposed biosensor is based on the FET operation with the advantage of amplification which provides a high sensitivity and a very low limit of detection. Hybrid metal oxide (ZnO and CuO) nanostructures have been synthesized in the form of hollow spheres (ZnO/CuO-NHS). The FET was fabricated by depositing ZnO/CuO-NHS on the interdigitated electrodes. Glucose oxidase (GOx) was immobilized successfully on the ZnO/CuO-NHS. Three different outputs of the sensor are examined, the FET current, the relative current change, and the drain voltage. The sensitivity of the sensor for each output type has been calculated. The readout circuit can convert the current change to the voltage change that has been used for wireless transmission. The sensor has a very low limit of detection of 30 nM with satisfactory reproducibility, good stability, and high selectivity. The electrical response of the FET biosensor towards the real human blood serum samples demonstrated that it can be offered as a potential device for glucose detection in any medical application.
Subject(s)
Biosensing Techniques , Zinc Oxide , Humans , Zinc Oxide/chemistry , Reproducibility of Results , Copper/chemistry , Electrodes , GlucoseABSTRACT
A high-performance non-enzymatic glucose sensor based on hybrid metal-oxides is proposed. Dumbbell-shaped double-shelled hollow nanoporous CuO/ZnO microstructures (CuO/ZnO-DSDSHNM) were prepared via the hydrothermal method using pluronic F-127 as a surfactant. This structure is studied by various physicochemical characterizations such as scanning electron microscopy, X-ray diffraction spectroscopy, inductively coupled plasma atomic emission spectroscopy, elemental mapping techniques, X-ray photoelectron spectroscopy, and transmission electron microscopy. This unique CuO/ZnO-DSDSHNM provides both a large surface area and an easy penetrable structure facilitating improved electrochemical reactivity toward glucose oxidation. The prepared CuO/ZnO-DSDSHNM was used over the glassy carbon electrode (GCE) as the active material for glucose detection and then coated by Nafion to provide the proposed Nafion/CuO/ZnO-DSDSHNM/GCE. The fabricated glucose sensor exhibits an extremely wide dynamic range from 500 nM to 100 mM, a sensitivity of 1536.80 µA mM-1 cm-2, a low limit of detection of 357.5 nM, and a short response time of 1.60 s. The proposed sensor also showed long-term stability, good reproducibility, favorable repeatability, excellent selectivity, and satisfactory applicability for glucose detection in human serum samples. The achieved high-performance glucose sensing based on Nafion/CuO/ZnO-DSDSHNM/GCE shows that both the material synthesis and the sensor fabrication methods have been promising and they can be used in future researches.
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A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddition reaction between aldehyde, hydroxylamine and sodium azide in the presence of Cu/C. The reaction probably proceeds by the in situ formation of nitriles followed by successive [3+2]cycloaddition with sodium azide. A variety of aldehydes were used to obtain the corresponding tetrazoles. The catalyst was recovered by simple filtration and reused at least five times without significant loss of catalytic activity. The use of this method offers additional advantages for the synthesis of 5-substituted 1H-tetrazole derivatives, including the easy availability of starting materials, mild conditions, experimental simplicity and good yields.
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Air pollution and dust storms are associated with increased cardiovascular hospital admissions. The aim of this study was to investigate the association between short-term exposure to ambient air pollutants and CVD (cardiovascular disease) events in a long-term observational period. The study included the events of cardiovascular diseases (namely coronary artery disease, ischemic heart disease, myocardial infarction, and pneumo thrombo embolism) within the population of Shiraz, from March 21, 2009 to March 20, 2015. Also, each patient's demographics were recorded. Main meteorological variables and five ambient pollutants (CO, O3, SO2, NO2, and PM10) were recorded. Statistical analysis was performed using linear regression (GLM) and a generalized additive model (GAM) estimating Poisson distribution and adjusted for the main risk factors and ambient meteorological variables. A mild prevalence (51.5%) of coronary artery disease (CAD) was registered in 6425 events. In GLM analysis, we observed an association among the pollutants with the coronary artery disease hospital admissions which was in the order of CO, NO2, and PM10. The highest association of each pollutant with hospital admission was observed as PM10 at lag 4 (RR = 1.08; 95% CI 1.02, 1.14 and p < 0.05), NO2 at lag 0 (RR = 1.22; 95% CI 1.00, 1.48), and CO at lag 0 (RR = 1.52 95% CI = (1.16, 1.99)). However, on dusty days, there were significantly higher numbers of referrals of cardiovascular patients (mean = 7.54 ± 4.44 and p = 0.002,) than on non-dusty days. According to these data, dust storms and some types of pollutants in the air are responsible for more admissions to hospitals for cardiovascular problems.
Subject(s)
Air Pollutants/toxicity , Cardiovascular Diseases/chemically induced , Adolescent , Adult , Aged , Air Pollution , Female , Hospitalization , Humans , Iran , Linear Models , Male , Middle Aged , Poisson Distribution , Risk Factors , Young AdultABSTRACT
A novel fluorescence chemical sensor for the highly sensitive and selective determination of Co(2+) ions in aqueous solutions is prepared. The cobalt sensing system was prepared by incorporating 7-[(5-chloro-8-hydroxy-7-quinolinyl)methyl]-5,6,7,8,9,10-hexahydro-2H-1,13,4,7,10-benzodioxatriazacyclopentadecine-3,11(4H,12H)-dione (L) as a neutral cobalt-selective fluoroionophore in the plasticized PVC membrane containing sodium tetraphenylborate as a liphophilic anionic additive. The response of the sensor is based on the strong selective fluorescence quenching of L by Co(2+) ions. At a pH 5.0, the proposed sensor displays a calibration curve over a wide concentration range of 5.0 x 10(-7) to 2.0 x 10(-2)M with a relatively fast response time of less than 5 min. In addition to high stability and reproducibility, the sensor shows a unique selectivity towards Co(2+) ion with respect to common coexisting cations. The proposed fluorescence optode was successfully applied to the determination of cobalt content of vitamin B12 ampoule, cobalt cake, cobalt alloy and tap water samples.