A photoredox and copper‐catalyzed sulfonylphosphorothiolation of alkenes has been developed. With the use of readily available aryl or alkyl sulfonyl chlorides as radical precursors and (RO)2P(O)SH ...as coupling partners, a wide range of decorated β‐sulfonyl phosphorothioates could be obtained in 37–98% yields with good functional group tolerance. Importantly, this three‐component reaction can be conveniently extended to late‐stage modification of bioactive molecules and gram‐scale synthesis.
•New α-aminophosphonic and α-aminophosphinic acids were synthesized and characterized.•Structural and spectral analysis of the synthesized acids was performed.•Anti-diabetic, anti-alzheimer and ...antioxidant activities have been evaluated in vitro.•DFT method at B3LYP/6–31 G (d,p) has been used to correlate experimental results.•The synthesized acids are potential inhibitors of SARS-CoV-2 main protease.
Two new α-aminophosphinic (A) and α-aminophosphonic (B) acids were synthesized through a one-pot three-component reaction with good yields of 89% and 85%, respectively. The NMR and mass spectroscopies have been used to identify the obtained compounds and confirm their structures, while the IR spectroscopy has been used to characterize functional groups and the type of vibrations involved for the studied compounds. Moreover, the examination of the structural properties and the comparison between the theoretical and the experimental results have been performed using DFT/B3LYP/6–31 G (d,p) method. Consequently, the calculated values of the total energy and the energy gap indicate that the (B) is more stable and less reactive than the (A). Also, MEP maps show that oxygen atoms are the probable sites of electrophilic reactions. In this context, the high reactivity of the (A) can be related to the replacement of the (OH) functional group by a hydrogen atom. Further, six in vitro assays have been used to evaluate the antioxidant potential of (A) and (B), which illustrate that both compounds exhibited an excellent activity (e.g., DPPH/IC50(B): 2.42 µg/mL and DPPH/IC50(A): 2.10 µg /mL). The anti-Alzheimer and antidiabetic effects of the studied compounds have been estimated in vitro by evaluating their inhibition of acetylcholinesterase, butyrylcholinesterase and α-glucosidase. The both compounds showed a good inhibitory activity for α-glucosidase (IC50(A): 12.63 and IC50(B): 25.26 µg/mL), and exhibited higher inhibitory activity against butyrylcholinesterase (BChE) than against acetylcholinesterase (AChE) (IC50(A): 36.71±0.95 and IC50(B): 26.56±1.32 µg/mL). Furthermore, the in silico docking study of the inhibitory action of SARS-CoV-2 main protease (Mpro) showed that (A) and (B) have a significant inhibitory action with total energy values of - 96.23 and - 99.99 kcal/mol, respectively.
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A three‐component reaction of a 1,2‐amino alcohol or 1,3‐amino alcohol with a formaldehyde solution and a propiolic acid was developed and studied. This new strategy provided an efficient access to ...biologically and synthetically important N‐propargyl oxazolidines, 1,3‐oxazinanes and thiazolidine bearing a diverse range of substituents in good yields. The transformation involves a cascade process that begins with an annulation and is followed by the metal‐free decarboxylative coupling.
A new three‐component strategy from aldehyde, p‐toluenesulfonyl hydrazide and potassium thiocyanate for the synthesis of 2‐aminothiadiazoles promoted by I2 under metal‐free conditions has been ...described. Potassium thiocyanate was used as an odorless and low‐toxicity sulfur source. A wide range of aromatic aldehydes can smoothly undergo the three‐component cyclization reaction under the optimized conditions to give the corresponding products in moderate to good yields.
A new three‐component strategy using aldehyde, p‐toluenesulfonyl hydrazide, and potassium thiocyanate for the synthesis of 2‐aminothiadiazoles promoted by I2 under metal‐free conditions has been described.
•Sixteen novel polyheterocyclic compounds were created in high yields (>80%) via three-component reaction.•The synthesized compounds showed good to high cytotoxicity against MCF-7 cancer cell ...line.•The products demonstrated high to excellent anti-oxidant activities.•These compounds exhibited moderate antibacterial properties only against Gram-positive bacteria.
In this study, pyrano3,2-epyrazaolo1,5-apyrimidine derivatives were produced in high yields (80–89%), at room temperature, by three-component reactions involving alkyl isocyanides, dialkyl acetylenedicarboxylates, and 7‑hydroxy pyrazolo1,5-apyrimidines. Using FT-IR, 1H and 13C NMR, and mass spectral data, the structure of the synthesized compounds was identified. The created molecules were tested against cancer, bacteria, and free radicals to evaluate how effective they could be. It was determined whether or not the tested substances had any cytotoxic effects on the MCF-7 (breast cancer) and the MCF-10 (breast epithelial) cell lines. Compound 4l, in comparison to other compounds, has shown the most potent anti-cancer activity (IC50=19.70±0.89 µM), which is roughly as excellent as the standard medicine etoposide (IC50= 18.71±1.09 µM). Also, the antioxidant properties of the products were investigated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The results demonstrated that compound 4 h had the highest free radical scavenging effect (IC50= 12.12±0.40 µM), which was very close to the value for ascorbic acid (IC50= 11.85±0.30 µM), as the antioxidant standard. The Kirby-Bauer disk diffusion technique was applied to examine the bactericidal impact of the synthesized compounds. According to the findings, virtually all the compounds had a modest level of action against Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus).
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Herein, we present a (NH4)2S2O8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis of various ...phosphorothioate‐containing quinoxalin‐2(1H)‐one derivatives (46 examples) in 37–79% yields. The reaction is compatible with a range of functional groups and is easily adaptable to large‐scale synthesis. Preliminary studies suggest the involvement of phosphorothioate radicals in these transformations.
The additive‐free 1,3‐dipolar cycloaddition reaction of isatin‐derived azomethine ylides with α‐cyano‐α,β‐unsaturated compounds was developed, which enabled diversity‐oriented synthesis of a series ...of novel and structurally complex 3,3′‐pyrrolidinyl‐spirooxindoles derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 92%) and excellent diastereoselectivities (up to >25:1 dr). The reaction displays switchable regioselectivity depending on the steric effect of the substrates.
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A cost‐effective protocol has been used for the synthesis of novel benzogbenzo4,5imidazo2,1-bquinazoline derivatives. This domino, one‐pot, three‐component reaction was carried out ...between 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes, and 2-aminobenzimidazole in the presence of piperidine in DMF solvent. This protocol has several advantages such as a convenient operational process, easy access to raw material, good yields and simple work-up. The structure of these compounds were characterized by spectroscopic techniques such as IR, 1H NMR, 13C NMR and CHN analysis.
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•A metal-free CC bond cleavage and CS, CN formation reaction.•Sulfur serves as both a raw material and an oxidant for CC bond cleavage.•Secondary amines and amides are both feasible ...nitrogen sources.
A metal-free CC bond cleavage reaction of β-nitrostyrenes in the presence of elemental sulfur and secondary amines/amides is described. Elemental sulfur serves as both a raw material and an oxidant for CC bond cleavage, and secondary amines or amides are both feasible nitrogen sources. Besides mild reaction condition and simple work-up procedure, the method provided thioamides with good to excellent yields.
