Search Results (106)

In this study, novel fluorescent 5-aryl-2-styryl-3H-indole derivatives were efficiently synthesized from 4-bromophenylhydrazine hydrochloride using the microwave-accelerated one-pot technique, which includes Fischer synthesis, Suzuki cross-coupling, and Knoevenagel condensation. The structural assignments of the synthesized compounds were based on ¹H, ¹³C, ¹⁵N, and ¹⁹F NMR; IR spectroscopy; and HRMS spectral data. The optical properties of the newly obtained styryl-indole dyes were studied using UV-vis and fluorescence spectroscopy, which clearly demonstrated that the derivatives substituted with electron-donating or -withdrawing groups exhibited varying emission shifts and quantum yields ranging from negligible to high. Full article

Peptoids are peptidomimetics in which the side chain is attached to the nitrogen of the amide group rather than the α-carbon. This alteration in the backbone structure is highly valued because it endows beneficial properties, including enhanced resistance to proteolysis, greater immunogenicity, improved biostability, and superior bioavailability. In this current study, we focused on the Ugi-4CR-based one-pot synthesis of peptoids using 1,4-dithiane-2,5-diol as the carbonyl component together with amine, carboxylic acid, and isocyanides. Four new peptoids—5a, 5b, 5c, and 5d—were designed and efficiently prepared in good chemical yields and were subjected to DFT investigations for their electronic behavior. These compounds have free OH, SH, and terminal triple bonds for further chemistry. In a computational analysis, the spectral data of compounds 5a–5d were juxtaposed with calculated spectral values derived from the B3LYP/6-311G(d,p) level. The electronic excitation and orbital contributions of 5a–5d were predicted using TD-DFT calculations. A natural bond order (NBO) analysis was utilized to investigate the electronic transition of newly synthesized peptoids, focusing on their charge distribution patterns. Furthermore, MEP and NPA analyses were conducted to predict charge distribution in these compounds. The reactivity and stability of the targeted peptoids were evaluated by global reactivity descriptors, which were determined with frontier molecular orbital analysis. The DFT results revealed that compound 5c displayed marginally higher reactivity compared to 5a, 5b, and 5d, possibly due to its extended conjugation. Full article

Tetrasubstituted furans and their derivatives represent a versatile class of important heterocyclic frameworks widely distributed in natural products. These scaffolds also demonstrate significant potential in pharmaceutical chemistry, materials science, and organic synthesis methodologies. In this study, we successfully established a synergistic catalytic system utilizing benzoylacetonitriles, aldehydes, and benzoyl chlorides as substrates, facilitated by tributylphosphine and immobilized lipase (Novozym 435), to achieve efficient synthesis of cyano-containing tetrasubstituted furans. Under optimized conditions, we obtained a series of target products exhibiting exceptional substrate tolerance with good to excellent isolated yields ranging from 80% to 94%. Additionally, we proposed a reasonable reaction mechanism and verified it through controlled experiments. This methodology not only expands the synthetic utility of lipase in non-natural transformations but also establishes a paradigm of green chemistry for the construction of tetrasubstituted furans. Full article

A pseudo-multicomponent one-pot protocol for the synthesis of 1,3-disubstituted imidazolidin-2-one is described, employing trans-(R,R)-diaminocyclohexane for the in situ formation of the Schiff base, followed by reduction to produce the respective diamine and cyclization with carbonyldiimidazole (CDI). This approach utilizes statistical analysis to optimize the reaction conditions, allowing a pseudo-multicomponent protocol to be proposed. The developed method demonstrates sustainability, efficiency, and potential applications in green chemistry, achieving yields ranging from 55% to 81%. This represents a significant advance in synthesizing heterocyclic compounds with biological and pharmacological applications. Full article

The one-pot multicomponent aza-Morita–Baylis–Hillman (MBH) reaction was performed under green conditions using 1,4-diazabicyclo[2.2.2]octane (DABCO) and Amberlyst^® 15 as a co-catalyst, at ambient temperature and under negligible amounts of non-hazardous solvent. A number of α-methylene-β-amino acid derivatives were produced in good to excellent yields from different arylaldehydes, p-toluenesulfonamide and α,β-unsaturated carbonyl compounds. The environmental benignity of the process is accounted by the low E-factor (0.7) and high atom economy (95%) values obtained. Full article

A series of new quinazolin-2,4-dione derivatives incorporating amide/eight-membered nitrogen-heterocycles 2a–c, in addition, acylthiourea/amide/dithiolan-4-one and/or phenylthiazolidin-4-one 3a–d and 4a–d. The starting compound 1 was prepared by reaction of 4-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzoyl chloride with ammonium thiocyanate and cyanoacetic acid hydrazide. The reaction of 1 with strong electrophiles, namely, o-aminophenol, o-amino thiophenol, and/or o-phenylene diamine, resulted in corresponding quinazolin-2,4-dione derivatives incorporating eight-membered nitrogen-heterocycles 2a–d. Compounds 3a–d and 4a–d were synthesized in good-to-excellent yield through a one-pot multi-component reaction (MCR) of 1 with carbon disulfide and/or phenyl isocyanate under mild alkaline conditions, followed by ethyl chloroacetate, ethyl iodide, methyl iodide, and/or concentrated HCl, respectively. The obtained products were physicochemically characterized by melting points, elemental analysis, and spectroscopic techniques, such as FT-IR, ¹H-NMR, ¹³C-NMR, and MS. The antibacterial efficacy of the obtained eleven molecules was examined in vitro against two Gram-positive bacterial strains (Staphylococcus aureus and Staphylococcus haemolyticus). Furthermore, Computer-Aided Drug Design (CADD) was performed on the synthesized derivatives, standard drug (Methotrexate), and reported antibacterial drug with the target enzymes of bacterial strains (S. aureus and S. haemolyticus) to explain their binding mode of actions. Notably, our findings highlight compounds 2b and 2c as showing both the best antibacterial activity and docking scores against the targets. Finally, according to ADMET predictions, compounds 2b and 2c possessed acceptable pharmacokinetics properties and drug-likeness properties. Full article

As an important component of LIBs, the electrode material plays a crucial role in determining the lithium (Li) storage performance in LIBs. In this study, MoS₂ nano-flowers were synthesized using a one-pot hydrothermal method. The resulting MoS₂ nano-flower, along with PAN, were used as raw materials for electrospinning. After annealing treatment, MoS₂/(carbon nanofibers) CNFs nano-composites coated with carbon fibers were formed. The CNFs coating exhibited electrical conductivity and enhanced structural stability of the MoS₂ due to the stabilizing effect of the carbon fibers. Additionally, electrochemical tests, including CV and GCD, indicated that the optimal capacity and cycling stability were achieved when the MoS₂ content was 10%. The results indicated that the charge/discharge capacity of MoS₂/CNFs-10% at a current density of 100 mA/g was ~650 mAh/g. After the cycling current returned to 100 mA/g, the current recovery was ~600 mAh/g, thereby indicating outstanding cycling stability. Accordingly, our fabrication technique and new insight could both widen design strategy of multicomponent composite electrode materials and promote the practical applications of the latest emerging transition metal sulfides in next-generation high-performance lithium-ion batteries. Full article

Imidazo[1,2-a]pyridines (IMPs) are valuable heterocycles, present in bioactive compounds and drugs. Analogs that incorporate azide moieties are useful intermediates in organic synthesis and can be used as synthetic platforms to access more complex products. Isocyanide-based multicomponent reactions such as Groebke–Blackburn–Bienaymé (GBB-3CR) are versatile tools to synthesized IMPs, in which orthogonal reagents are included into components to increase its synthetic potential. Herein we developed a one-pot process to access IMPs functionalized with azides under mild conditions, which are synthetic platforms for further post-transformations. Full article

In the present report, we have described the synthesis of N-aminopolyhydroquinoline (N-PHQ) derivatives using highly efficient β-cyclodextrin (β-CD) as a catalyst by the Hantzsch condensation of substituted aromatic aldehydes, dimedone, and hydrazine hydrate in one pot. The reactions were completed in a shorter time without the generation of any other byproduct. The synthesized N-PHQs were washed thoroughly with distilled water and recrystallized with ethanol to get highly purified products (as crystals). The structure of the synthesized N-PHQs was established by using advanced spectroscopic techniques like FT-IR, NMR (¹H, ¹³C, DEPT, COSY, and HSQC), ESI-MS, and Elemental Analyzer. The N-PHQs derivatives demonstrated moderate to excellent resistance against the tested strains (both fungal as well as bacterial). The presence of polar groups, which are able to form H-bonds, attached to the phenyl ring like -NO₂ (4b and 4c), and -OMe (4i, 4j, and 4k) exhibits excellent activity, which is comparable to standard drugs, amoxicillin and fluconazole. Full article

Anthranilic acids, salicylaldehydes and arylboronic acids reacted in EtOH/H₂O (1/3) at 150 °C under microwave irradiation for 1 h to give, in excellent yields and purity, twenty-three bridgehead bicyclo[4.4.0]boron heterocycles via one-pot, three-component green synthesis. The scope and the limitations of the reactions are discussed in terms of the substitution of ten different anthranilic acids, three salicylaldehydes and three arylboronic acids. The replacement of salicylaldehyde with o-hydroxyacetophenone demanded a lipophilic solvent for the reaction to occur. Eight novel derivatives were isolated following crystallization in a toluene-containing mixture that included molecular sieves. The above one-pot, three-component reactions were completed under microwave irradiation at 180 °C within 1.5 h, thus avoiding the conventional prolonged heating reaction times and the use of a Dean–Stark apparatus. All derivatives were studied for their affinity to calf thymus DNA using proper techniques like viscosity and UV–vis spectroscopy, where DNA-binding constants were found in the range 2.83 × 10⁴–8.41 × 10⁶ M⁻¹. Ethidium bromide replacement studies using fluorescence spectroscopy indicated Stern–Volmer constants between 1.49 × 10⁴ and 5.36 × 10⁴ M⁻¹, whereas the corresponding quenching constants were calculated to be between 6.46 × 10¹¹ and 2.33 × 10¹² M⁻¹ s⁻¹. All the above initial experiments show that these compounds may have possible medical applications for DNA-related diseases. Full article

We have synthesized 22 symmetric and asymmetric 4-aryl-1,4-dihydropyridines (1,4-DHPs) by a “green” microwave-assisted one-pot multicomponent Hantzsch reaction and evaluated their cytotoxicity to three human cancer cell lines regarding U-251MG (human glioblastoma), HeLa 229 (human cervical adenocarcinoma), and MCF-7 (human breast carcinoma). None of the 1,4-DHPs were cytotoxic to U-251MG cells. Most of the 1,4-DHPs did not affect HeLa 229 or MCF-7 cell viability. On the other hand, symmetric 1,4-DHPs 18 (diethyl 4-(4-benzyloxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate), 19 (diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate), and 20 (diethyl 4-(3-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate) reduced the HeLa (IC₅₀ = 3.6, 2.3, and 4.1 µM, respectively) and MCF-7 (IC₅₀ = 5.2, 5.7, and 11.9 µM, respectively) cell viability. These 1,4-DHPs were more cytotoxic to the HeLa and MCF-7 cells than to the GM07492 (normal human fibroblast) cells, as evidenced by their selectivity indexes. Therefore,1,4-DHPs 18, 19, and 20 may serve as novel lead compounds to discover other 1,4-DHP derivatives with improved anticancer potency and selectivity. Full article

This manuscript serves as the starting point for in-depth research of multicomponent, statistical, methacrylate-based copolymers that potentially mimic the behavior of proteins in aqueous solutions. These synthetic macromolecules are composed of specially chosen comonomers: methacrylic acid (MAA), oligoethylene glycol methyl ether methacrylate (OEGMA₄₇₅), 2-(dimethylamino)ethyl methacrylate (DMAEMA) and benzyl methacrylate (BzMA). Monomer choice was based on factors such as the chemical nature of pendant functional groups, the polyelectrolyte/polyampholyte and amphiphilic character and the overall hydrophobic–hydrophilic balance (HLB) of the obtained quaterpolymers. Their synthesis was achieved via a one-pot reversible addition fragmentation chain transfer (RAFT) polymerization in two distinct compositions and molecular architectures, linear and hyperbranched, respectively, in order to explore the effects of macromolecular topology. The resulting statistical quaterpolymers were characterized via ¹H-NMR and ATR-FTIR spectroscopies. Their behavior in aqueous solutions was studied by dynamic (DLS) and electrophoretic light scattering (ELS) and fluorescence spectroscopy (FS), producing vital information concerning their self-assembly and the structure of the formed aggregates. The physicochemical studies were extended by tuning parameters such as the solution pH and ionic strength. Finally, the quaterpolymer behavior in FBS/PBS solutions was investigated to test their colloid stability and biocompatibility in an in vivo-mimicking, biological fluid environment. Full article

(1) Background: A molecular hybridization docking approach was employed to develop and detect a new category of naturally activated compounds against Culex pipiens as acetylcholinesterase inhibitors via designing a one-pot multicomponent nano-delivery system. (2) Methods: A nanostructure lipid carrier (NLC), as a second generation of solid lipid nanoparticles, was used as a carrier to deliver the active components of curcumin (Cur), geraniol (G), and linalool (L) in one nanoformulation after studying their applicability in replacing the co-crystallized ligand imidacloprid. (3) Results: The prepared nanostructure showed spherical-shaped, polydisperse particles ranging in size from 50 nm to 300 nm, as found using a transmission electron microscope. Additionally, dynamic light scattering confirmed an average size of 169 nm and a highly stable dispersed solution, as indicated by the zeta potential (−38 mV). The prepared NLC-Cur-LG displayed competitive, high-malignancy insecticidal activity against fourth instar C. pipiens with an elevated rate of death of 0.649 µg/mL. The treatment, due to the prepared nanostructure, affects oxidative stress enzymes, e.g., hydrogen peroxide (4 ppm), superoxide dismutase (SOD) (0.03 OD/mg), and protein carbonyl (0.08 OD/mg), and there are observable upward and downward fluctuations when using different concentrations of NLC-Cur-LG, suggesting significant problems in its foreseeable insecticidal activity. The acetylcholinesterase activity was assessed by an enzyme inhibition assay, and strengthened inhibition occurred due to the encapsulated NLCs (IC₅₀ = 1.95 µg/mL). An investigation of the gene expression by Western blotting, due to treatment with NLC-Cur-LG, revealed a severe reduction of nearly a quarter of what was seen in the untreated group. As a preliminary safety step, the nanoformulation’s toxicity against normal cell lines was tested, and a reassuring result was obtained of IC₅₀ = 158.1 µg/mL for the normal lung fibroblast cell line. (4) Conclusions: the synthesized nanoformulation, NLC-Cur-LG, is a useful insecticide in field conditions. Full article

One-pot reactions offer advantages like easy automation, higher product yields, minimal waste generation, operational simplicity, and thus reduced cost, time and energy. This review presents a comprehensive overview of one-pot reactions including triethyl orthoformate and amines as valuable and efficient reagents for carrying out two-, three- or four-component organic reactions. Full article

2-Hydroxypyridines (or commonly named 2-pyridones) are widespread nitrogen heterocycles in natural and synthetic products and their applications in biological, pharmaceutical and agrochemical compounds are becoming increasingly important. Therefore, several procedures have been described in the literature for the preparation of this heterocyclic framework. Among them, multicomponent reactions are the currently practiced method in synthetic organic chemistry, where reduced reaction times, high yields, and ease of product isolation are the main benefits of this method. In order to study the effect of the aforementioned method under greener medium, we herein describe a novel one-pot route for the design of 4,6-diaryl-3-cyano-2-pyridone derivatives under free solvent conditions. The three-component condensation of alkenes, ketones, and ammonium acetate efficiently resulted in the target heterocycles, with higher yields within a short time reaction compared to the classical method. Full article