We report here our results on the application of ynamides as substrates in the reactions with diorganyl dichalcogenides and iron(III) chloride to give selectively three different types of compounds: E-αchloro-β-(organoselenyl)enamides, 4-(organochalcogenyl)oxazolones, and vinyl tosylates. The results reveal that the selectivity in the formation of products was obtained by controlling the functional groups directly bonded to the nitrogen atom of the ynamides. Thus, α-chloro-β-(organoselenyl) enamide derivatives were exclusively obtained when the TsN-and MsN-ynamides were treated with a mixture of diorganyl diselenides (1.0 equiv) and FeCl 3 (3.0 equiv) in dichloroethane (DCE, 3 mL), at room temperature. The 4-(organochalcogenyl)oxazolones were selectively obtained with ynamides having an ester group, directly bonded to the nitrogen atom, upon treatment with a solution of FeCl 3 (1.5 equiv) and diorganyl dichalcogenides (1.0 equiv) in dichloromethane (3 mL) at room temperature. Finally, vinyl tosylates were obtained from ynamides having an ester group, directly bonded to the nitrogen atom, by reaction with p-toluenesulfonic acid. We also studied the application of the prepared compounds as substrates for Suzuki and Sonogashira cross-coupling reactions.
The aim of this study was evaluating the effects of jabuticaba aqueous extract (JPE ‐ 0.5 g/kg) on serum lipid levels, immune system, and oxidative stress parameters of streptozotocin‐induced diabetic rats. Administration of JPE for 30 days, by gavage, was able to reduce serum levels of total cholesterol, non‐high density lipoprotein (HDL) cholesterol, and triglycerides in diabetic rats. The HDL cholesterol levels increased in both diabetic and healthy rats after JPE treatment. Total leukocyte and lymphocyte counts reduced in diabetic rats, and JPE treatment prevented these diabetes mellitus (DM)‐induced changes in the immune system. In addition, the induction of DM also led to dysregulation in the activity of superoxide dismutase and catalase antioxidant enzymes as well as an increase in oxidative stress markers. Treatments with JPE reduced oxidative stress and modulated antioxidant enzyme activities. These data demonstrate the potential of JPE as an adjuvant treatment option for diabetic patients. Practical applications Considering that it is very common to observe dyslipidemia in diabetic patients and that these alterations, combined with the increased oxidative stress levels, also common in these patients, can lead to the development of cardiovascular diseases, JPE would be an alternative treatment adjunct to reduce these risks. In addition, although more studies are needed, JPE has the potential to improve the count of total lymphocytes and leukocytes, which could assist in improving the immune response of these patients, who also commonly have a higher risk of infectious diseases. Thus, JPE could be used by these patients, in combination with conventional treatment, in the form of a nutraceutical rich in phenolic compounds.
The selective synthesis of 4-alkynyloxazolones and their further applications as substrates to electrophile-promoted nucleophilic cyclization have been developed. The reaction of ynamides with terminal alkynes proceeded smoothly to give 4alkynyloxazolones in the presence of a catalytic amount of palladium(II) acetate. The products were obtained with the sequential formation of new C−C and C−O bonds via a cascade procedure. The first step involved a carbon−oxygen bond formation, via a 5endo-dig closure, which was confirmed by X-ray analyses of the crystalline sample. Subsequently, the reaction of 4-alkynyloxazolones with an electrophilic selenium source gave 3-phenylselanyl benzofuran derivatives via an electrophile-promoted nucleophilic cyclization.
Context. Chaptalia nutans (L.) Pol. (family: Asteraceae) is widely used in traditional medicine as laxative and anticough medications and especially in the traumatisms, wounds, and hemorrhages in topical preparations. Objective. This work was to evaluate the chemical constitution of the hydromethanolic (30/70 methanol-water) macerating extract obtained from the leaves of C. nutans, as well as to study the antioxidant, antimicrobial, cytotoxic, and genotoxic activity of the species. Materials and methods. Phytochemical screening, antioxidant activity (total phenolic, total flavonoid, condensed tannins content, DPPH radical, and FRAP), antibacterial activity (P. aeruginosa, B. cereus, E. epidermidis, E. coli, S. aureus, E. faecalis, P. mirabilis, Candida glabrata (clinical isolate), Candida tropicalis (clinical isolate), C. krusei (clinical isolate), and C. albicans (clinical isolate)), and oxidative stress parameters (TBARS, carbonyl protein, and DCFH) were analyzed according to the literature. Toxicity of C. nutans was evaluated using an alternative method, D. melanogaster, as well as a locomotor assay. Results. The phytochemical screening test of methanolic leaves extract revealed the presence of alkaloids, coumarins, quaternary bases, phenolics, flavonoids, tannins, and free steroids. A quantitative phytochemical study indicated the total phenol (30.17 ± 1.44 mg/g), flavonoid (21.64 ± 0.66 mg/g), and condensed tannins (9.58 ± 0.99 mg/g). DPPH (345.41 ± 5.35 μg/mL) and FRAP (379.98 ± 39.25 μM FeSO4/mg sample) show to extract of C. nutans leaves an intermediate value, indicating moderate antioxidant activity of the extract. Antibacterial results revealed only a positive result (antimicrobial activity) for the hexane fraction which significantly inhibited the microorganisms E. epidermidis, C. tropicalis, C. glabrata, and C. krusei at a concentration of 1000 μg/mL. TBARS, carbonyl protein, and DCFH demonstrate that the extract has the ability to protect the cell from protein and lipid damage, as well as the inhibition of oxygen-derived radicals at the three concentrations tested: 0.1, 1, and 10 mg/mL. Regarding the toxicity of C. nutans extract against D. melanogaster, it was found that until the concentration of 15 mg/mL, the extract showed no toxicity and that the LC50 obtained was 24 mg/mL. Results show that the C. nutans extract leaves used to prevent PQ damage were effective in reducing flies’ mortality and improving locomotor capacity. Conclusion. Our studies demonstrated for the first time that C. nutans crude leaf extract has high antioxidant capacity both in vitro and in vivo through different analysis techniques. These results make it possible to infer future applications in the pharmacological area, evidenced by the low toxicity observed in D. melanogatser, as well as the ability to neutralize different sources of RONS.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.