The development of rapid and efficient routes to alkene derivatives remains a significant priority due to their broad utility as building blocks and valuable compounds. Herein, we report a simple, general, and highly efficient procedure for the (catalytic) isomerization of alkenes under mild conditions. This method is applicable to a wide range of substrates, including allylic derivatives of benzenes, aromatic and aliphatic systems, heterocycles, ethers, thioethers, amines, and sulfones. In this transformation, KO t Bu acts as both the base and the proton shuttle, enabling the reaction to proceed under air and affording quantitative yields within minutes for the majority of the substrates examined. The reaction occurs under thermodynamic control, affording the most stable isomer (typically, the E-alkene).

Background/Objectives: The development of specific inhibitors for cyclooxygenase-2 (COX-2) is a challenge for public health. A series of 17 N-phthalimide hybrids was evaluated using a functional M06 meta-GGA hybrid in combination with a polarized 6-311G (d, p) basis set. The top three candidates (6, 10, and 17) were synthesized and evaluated as selective COX-2 inhibitors of PGE-2 using an integrated in silico–in vitro approach. Methods: Molecular docking against COX-2 (PDB 5KIR) and COX-1 (PDB 6Y3C), supported by homology modeling and DFT geometry optimization (B3LYP/6-31G*), revealed that the phthalimide carbonyl groups and the 3,4,5-trimethoxyphenyl or geranyl-derived moieties establish key hydrogen bonds and hydrophobic contacts with Arg120, Tyr355, Tyr385, and Ser530 in the COX-2 active site, conferring predicted selectivity ΔGCOX−2 vs. COX−1 = −1.4 to −2.8 kcal/mol. Results: The compounds complied with Lipinski’s and Veber’s rules and displayed favorable ADMET profiles. In vitro assessment in LPS-stimulated J774A.1 murine macrophages confirmed potent inhibition of PGE2 production, 3.05 µg/mL, with compound 17 exhibiting the highest efficacy, 97.79 ± 5.02% inhibition at 50 µg/mL, and 10 showing 95.22 ± 6.03% inhibition at 50 µg/mL. Notably, all derivatives maintained >90% cell viability up to 250 µg/mL by resazurin assay and showed no evidence of cytotoxicity or mitosis potential in the tests at 24 h. Conclusions: These results demonstrate that strategic hybridization of phthalimide with natural and synthetic product-derived fragments yields highly potential PGE2 inhibitors. Therefore, compounds 6, 10, and 17 are promising lead candidates for the development of safer anti-inflammatory agents.

Extracts from the flowers and fruits of Sambucus nigra L. have various applications as colorants and adjuvants in the food, cosmetics, and pharmaceutical industries. It is therefore necessary to establish optimal conditions for the production of these extracts. The objective of this study was to compare different extraction conditions that allow the recovery of polyphenols and flavonoids with antioxidant activity from the aerial parts of S. nigra. For this purpose, the following extraction conditions were analyzed: maceration (M) and ultrasound-assisted (U), as well as extractant mixtures with five different proportions of ethanol and water; TPC and TFC were determined using spectroscopic methods, a preliminary analysis was performed by HPLC-DAD, and the content of chlorogenic acid and rutin was quantified. Similarly, the extracts were evaluated for their antioxidant capacity in ABTS, DPPH, and FRAP assays. Finally, PCA was performed to comprehensively analyze the relationship between the results obtained. The results showed that the extraction conditions determine the recovery of bioactive compounds such as polyphenols and antioxidant activity, with the highest yields obtained with 4M and 5M, and the extracts with the highest TPC and TFC being 5U and 1M, respectively. Likewise, the highest concentrations of chlorogenic acid and rutin were found in condition 2M, and the best antioxidant capacity was observed under extraction conditions 3U. This was confirmed by PCA, which indicated that extraction conditions influence yield, recovery of phenolic compounds, and antioxidant capacity. Therefore, these results indicate that there is no single condition that achieves the best parameters for this species, but rather that specific conditions must be applied depending on the metabolite groups and antioxidant activity.

Dinuclear silver N-heterocyclic carbene (Ag-NHC) complexes are readily accessible either by reacting imidazolium salts (e.g., Cl, Br, PF6, BPh4) with Ag2O or by the direct formation of the carbene from 1,3-disubstituted imidazol-2-ylidenes with a suitable base (e.g., KHMDS) followed by addition of silver salts (e.g., AgPF6). Many Ag-NHC complexes have shown considerable potential across various fields due to their versatile properties. Notably, the lability of silver-carbene bonds enables efficient ligand transfer to other transition metals, thereby enhancing catalytic, photophysical, antimicrobial, and anticancer activities -key topics discussed in this review. Complexes with square geometries are particularly effective as chemosensors, offering low detection limits, high sensitivity, and selectivity. In antimicrobial and anticancer research, complexes with lipophilic side chains, benzimidazole groups, and silver -silver interactions show encouraging results, in some cases surpassing standard drugs. Despite these advances, their catalytic potential remains underexplored, with current catalysts showing performance similar to mononuclear analogs. Future studies should focus on designing catalysts with cooperating silver centers and incorporating novel functionalities, such as halogenated imidazoles, to improve both biological activity and catalytic efficiency.

Polynuclear (tri-, tetra-, penta-, hexa-, polymeric-) silver N-heterocyclic carbene (Ag-NHC) complexes can be synthesized by reacting imidazolium salts (e.g., Cl, Br, PF6) with Ag2O, followed by anionic exchanges in some cases. The first polynuclear (tetra-) Ag-NHC complex was reported in 2002. Since then, these complexes have been explored in the literature for a variety of applications, including transmetallation, sensing, antimicrobial agents, and anticancer treatments, owing to their versatile properties. The labile silver-carbene bonds facilitate efficient ligand exchange with other transition metals such as Au, Cu, and Pd providing an efficient route to a variety of transition metal-NHC complexes with diverse applications. Tetranuclear Ag-NHC complexes that exhibit substantial fluorescence intensity have been used as sensors to detect persistent pollutants like 2,6-dichloronitroaniline with high sensitivity. Additionally, some trinuclear Ag-NHC complexes have demonstrated better antiproliferative activity than known chemotherapeutic drugs like 5-fluorouracil and cisplatin, highlighting the potential of these complexes as more stable and selective therapeutic agents. Overall, this review underscores the versatility of polynuclear Ag-NHC complexes across diverse fields, while emphasizing the importance of structural modifications to optimize their efficacy and minimize toxicity.

Background: This study investigates the synthesis and pharmacological potential of N-substituted isoindoline-1,3-dione (phthalimide) derivatives. Using the M06 meta-GGA hybrid functional with a polarized 6-311G(d,p) basis set, computational evaluations assessed their impact on apoptosis modulation in colon cancer cells. Molecular docking studies targeted the TGF-β protein (PDB: 1RW8) at the ALK5 binding site. On this study fourteen molecules were evaluated (P1–P14) and six (P1, P3, P4, P5, P7, and P13) demonstrated promising binding values. Methods: from the fourteen studied compounds five compounds (P2, P4, P7, P10, and P11) were successfully synthesized and fully characterized. The reactions were monitored via TLC and HPLC confirming high-purity compounds. Functional groups were identified through FTIR and structural characterization was supported by NMR analyses. Results: Density functional theory calculations and docking simulations allowed to classified the compounds as potential ALK5 inhibitors. Synthesized derivatives were developed in yields from 85 to 99% and showed better binding affinities than Capecitabine (−6.95 kcal/mol) used as control compound, with P7 (5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl 2-(1,3-dioxoisoindolin-2-yl) acetate) leading the group with a binding energy of −12.28 kcal/mol. Other synthesized compounds also exhibited significant affinities: P4 (−11.42 kcal/mol), P10 (−8.99 kcal/mol), P11 (−7.50 kcal/mol), and P2 (−7.22 kcal/mol). Conclusions: Integrating computational insights with experimental validation highlights the therapeutic potential of phthalimide derivatives, particularly P7. The study underscores a rigorous approach to identifying promising candidates for anticancer therapeutics, warranting further exploration.

Isoindoline-1,3-dione, also referred as phthalimide, has gained recognition as promising pharmacophore due to the documented biological activities of its derivatives. Phthalimides are a family of synthetic molecules that exhibit notable bioactivity across various fields, particularly as anticancer and anti-inflammatory agents. This review focuses on syntheses and anti-inflammatory studies of the reported phthalimide derivatives. Although there are several synthetic protocols to produce phthalimide derivatives, two methods for synthesizing phthalimides are traditionally used: reacting phthalic anhydride with amines or anilines and the Gabriel synthesis. Due to their structural versatility and established pharmacological effects, derivatives of phthalimides such as the commercially available drugs thalidomide, pomalidomide, and lenalidomide, have driven the development of new derivatives offering hundreds of promising drug candidates with exceptional therapeutic potential, such as LASSBio 468 and adducts 2, 9, 150, 241, 255, and 305 to name some.

In this manuscript, literature reports on mono- and di-halogen (F, Cl, Br, and I) substituted at positions 4 or/and 4,5 imidazol-2-ylidene (NHC) metal complexes are discussed: particularly, their structural diversity with various metals (groups 6-13), important physicochemical properties, catalytic and medicinal/biological applications are reviewed. To our knowledge, there are no literature reports on group 4 and 5 metal complexes with this type of NHC ligands. Halogenated imidazol-2-ylidene metal complexes deserve special attention because halogens are the classic electron donating groups (mesomerically) in conjugated aromatic/heteroaromatic ring systems, but electron withdrawing inductively. However, they exhibit a significant electron withdrawing inductive effect, thus providing unique electronic properties. This is important for fine tuning of σ-donor abilities of the "carbenic" carbon of imidazol-2-ylidenes, which directly affect catalytic performance of their metal complexes. Other applications, advantages, and disadvantages of halogenated vs. unsubstituted imidazol-2-ylidene metal complexes are critically analyzed and summarized in this review.

This research explores the diverse applications of copper(0) nanoparticles grafted onto boron carbon nitride nanosheets, using dill leaf extract as a natural reducing and stabilizing agent. This nanocatalyst efficiently catalyzes the synthesis of tetrazole and aniline derivatives, demonstrating good recyclability and promising potential in cancer therapy. By merging sustainability with innovation, this nanocatalyst offers transformative solutions in both synthesis and medical fields.

This communication reports a four-step protocol to produce 3-allyl-2-(allyloxy)-5-bromoaniline 5 from commercially available 2-allylphenol. The synthetic steps used were nitration, selective bromination, allylation, and reduction of the nitro group.

Sulfones are fascinating and highly used functional groups, but current syntheses still have limitations. Here, a regiodivergent transition metal-free approach towards sulfones [(E)-allylic sulfones and a-sulfonylmethyl styrenes] is reported. The method employs commercially available olefins, bases, additives, solvents, and sodium sulfinates (RSO2Na) and produces adducts in good yields. Considering that up to 4 reactions (bromination, dearomative rearrangement, E2, and S(N)2) are happening, this approach is very efficient. The structures of key adducts were confirmed by X-ray crystallography.

Polypropionate units are a common structural feature of many of the natural products in polyketides, some of which have shown a broad range of antimicrobial and therapeutic potential. Polypropionates are composed of a carbon skeleton with alternating methyl and hydroxy groups with a specific configuration. Different approaches have been developed for the synthesis of polypropionates and herein we include, for the first time, all of the epoxide-based methodologies that have been reported over the years by several research groups such as Kishi, Katsuki, Marashall, Miyashita, Prieto, Sarabia, Jung, McDonald, etc. Several syntheses of polypropionate fragments and natural products that employed epoxides as key intermediates have been described and summarized in this review. These synthetic approaches involve enatio- and diastereoselective synthesis of epoxides (epoxy-alcohols, epoxy-amides, and epoxy-esters) and their regioselective cleavage with carbon and/or hydride nucleophiles. In addition, we included a description of the isolation and biological activities of the polypropionates and related natural products that have been synthetized using epoxide-based approaches. In conclusion, the epoxide-based methodologies are a non-aldol alternative approach for the construction of polypropionate.

MXenes, two-dimensional (2D) materials that consist of transition metal carbides, nitrides and/or carbonitrides, have recently attracted much attention in energy-related and biomedicine fields. These materials have sub-stantial advantages over traditional carbon graphenes: they possess high conductivity, high strength, excellent chemical and mechanical stability, and superior hydrophilic properties. Furthermore, diverse functional groups such as-OH,-O, and-F located on the surface of MXenes aid the immobilization of numerous noble metal nanoparticles (NP). Therefore, 2D MXene composite materials have become an important and convenient option of being applied as support materials in many fields. In this review, the advances in the synthesis (including morphology studies, characterization, physicochemical properties) and applications of the currently known 2D MXene-metal (Pd, Ag, Au, and Cu) nanomaterials are summarized based on critical analysis of the literature in this field. Importantly, the current state of the art, challenges, and the potential for future research on broad applications of MXene-metal nanomaterials have been discussed.

Currently, in hospitals and community health centers, microbial infections are highly common diseases and are a leading cause of death worldwide. Antibiotics are generally used to fight microbial infections; however, because of the abuse of antibiotics, microbes have become increasingly more resistant to most of them. Therefore, medicinal chemists are constantly searching for new or improved alternatives to combat microbial infections. Coumarin triazole derivatives displayed a variety of therapeutic applications, such as antimicrobial, antioxidant, and anticancer activities. This review summarizes the advances of coumarin triazole derivatives as potential antimicrobial agents covering articles published from 2006 to 2022.

NHCs (N-heterocyclic carbenes) are generally used as organic ligands that can coordinate with metal ions like silver to form stable complexes. These complexes have shown enhanced antimicrobial properties compared to silver alone. This document provides an overview of the reported NHC-based silver derivatives (acetates, chlorides, bromides, and iodides) who possess antimicrobial activity. This review covers articles published between the first report (2006) and 2023.

Lycorane is a pentacyclic core presented in alkaloids isolated from the Amaryllidaceae family of herbaceous flowering plants. Members of this class of natural products have shown to display important biological properties including analgesic, antiviral, and antiproliferative activities. This review presents the known synthetic routes toward alpha-, beta-, gamma-, and delta-lycoranes. alpha-(19 routes), beta-(10 routes), gamma-(38 routes), and delta-(6 routes).

In this work, we have provided mechanistic insight into the addition of bromine to an allylic double bond of allylaryl derivatives using experimental and DFT-based electronic structure methods. The experimental yields indicate the influence of the functional group on the aryl ring on the ratio of 1,2-dibromo and 1,3-dibromo adducts formed in the reaction. The optimized geometry and the electron density maps of the allylaryls and their cationic intermediates from DFT simulations revealed that electron-rich aryl rings promoted formation of cationic spiro[2.5] intermediate II, whereas electron-poor aryl rings resulted in formation of bromonium intermediate I. It was observed that electron-rich allylaryls promoted the 1,2-shift of the aryl ring that resulted in bond formation between the carbon atom (C1) on the aryl ring and the central carbon atom (C3) in the allylic double bond and formed spiro[2.5] intermediate II, a trend which was confirmed by harmonic oscillator model of aromaticity index. Also, Wiberg bond order analysis is in good agreement with the experimental work. Thermochemical analysis indicates that smaller C1···C3 distance resulted in favorable values for the difference in free energy change (ΔΔG). The favorable ΔΔG values are a result of higher electron density on the aryl ring, making it more nucleophilic toward C3 carbon and promoting 1,2-shift that led to formation of the spiro[2.5] intermediate. Thus, the underlying mechanism indicates that the electron-rich allylaryls promote the formation of 1,3-dibromo compounds through formation and stabilization of the spiro[2.5] intermediate II.

The first biological inclusion in Cretaceous (Cenomanian) amber from Texas (USA) is here documented. Most of the Cretaceous ambers with biological inclusions are from Europe (Spain, France) and Myanmar (Asia). Although the coleopteran here reported is microscopic and incomplete, it preserves enough morphological details to be identified as a member of the Family Ptinidae Latreille, 1802. This antecedent is significative and reveals the potential of this Cretaceous amber to contain more diverse bioinclusions, since the paleoenvironment suggested by the sediments that contain the amber and the ecological affinity of recent representatives of the Ptinidae suggest a humid forest near an estuary, associated to deltaic plain deposits. Este hallazgo representa la inclusión biológica en ámbar más antigua en las Americas.

There is a growing interest in developing more efficient synthetic alternatives for the synthesis of nitrogen-containing allylic compounds. This article presents a straightforward two-step protocol to produce 5-(3-azidoprop-1-en-2-yl)benzo[d][1,3]dioxole 4 from the natural product safrole. The method yielded the expected α-azidomethyl styrene 4, in good yield, via a dearomative rearrangement.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.