The rapid advancement of technologies such as nanomedicine, personalized medicine, smart materials, and organic electronics presents vast opportunities for progress and addressing pressing social needs. Among these innovations, organic dyes stand out for their significant potential, as their production does not depend on non-renewable rare earth elements. This makes them an accessible and eco-friendly solution for creating high-performance materials.

A particularly promising class of organic dyes is 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) compounds. Its unique chemical structure is characterized by a boron–dipyrrin core, which offers several advantages, including strong absorption and emission in the visible-to-red region of the spectrum, high-fluorescence quantum yields, excellent stability and tunable optical properties through structural modifications. To harness the full potential of BODIPY compounds in sensing, biomedical and optoelectronic applications, it is essential to understand the impact of α-modifications on their structure-property relationships.

In this study, we have synthesized and explored the photophysical properties of a symmetric thienyl-substituted BODIPY alongside a pyrrolyl-substituted BODIPY. By comparing their absorption and emission spectra, amplified spontaneous emission, and stability characteristics, we aim to elucidate how these α-modifications influence their performance. This research not only contributes to the fundamental understanding of BODIPY chemistry but also to the developing of enhanced fluorescent probes with tailored functionalities for diverse applications in advanced sensing technologies and high-performance optoelectronic devices.

The p-aminobenzoate moiety has been demonstrated as a potent substructure in medicinal chemistry. Several derivatives have been synthesized and their antibacterial and anticancer activities have been analyzed, yielding promising results.

In glycodrugs, the specific biological activity cannot be exclusively attributed to the aglycone moiety. It has been well demonstrated that the sugar residue may play a crucial role in therapeutic efficiency by modifying transport through various biological barriers or interacting with receptors or lectins on the cell surface.

In the present work, we investigate the synthesis and structural analysis of novel benzocaine and procaine glyco derivatives. The molecule design incorporates two principles: the attachment of the bioactive aglycone at a non-anomeric position and through a nitrogen atom; these structural features generate novel compounds that differ from classical O-glycosides, thereby creating molecular diversity to achieve more accurate structure-activity relationships.

We synthesized 6-N-galactosyl derivatives of p-aminobenzoate using a four-step methodology in good yields. The oxidation of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose with DMSO/DCC yielded the corresponding galactosyl aldehyde. This aldehyde subsequently reacted with arylamines (benzocaine or procaine) in dichloromethane, forming the Schiff bases. The imine functional group was then reduced with NaBH₄ in isopropanol. The resulting galactosyl derivatives of procaine and benzocaine were fully characterized using NMR spectroscopy. A comprehensive conformational analysis was also conducted, analyzing ¹H NMR coupling constants and comparing the results with previously reported 6-deoxy-6-N-aryl-D-galactosides.

The pyrimidine moiety is a crucial heterocyclic compound widely present in the human body, exhibiting diverse biological activities such as antimicrobial, anti-inflammatory, anti-coagulant, antihypertensive, and antitubercular properties. It is integral to nucleic acids and enzymes in living organisms, offering potential as both antagonist and agonist drugs.

The rise of resistance to antibiotics and other antimicrobial agents poses a significant global challenge today. As microbes develop resistance to current treatments, the battle between bacteria and humans intensifies, often resulting in adverse outcomes for human health. Addressing these challenges requires controlling the overuse of antibiotics, which exacerbates resistance, and developing novel antibiotics with enhanced potency and efficacy.

To mitigate these challenges and improve treatment outcomes, discovering new antimicrobial agents with improved safety profiles remains paramount. This study focuses on the synthesis and evaluation of novel pyrimidine derivatives as potential antimicrobial agents, aiming to contribute to the ongoing efforts against microbial resistance.

In this study, we synthesized and assessed the antimicrobial activity of novel 5-arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-ones. All the synthesized derivatives were meticulously characterized and their structures confirmed through spectroscopic analysis. These compounds exhibited significant activity against both bacterial and fungal agents, highlighting their potential as effective antimicrobial agents. As we continue to face evolving challenges in microbial resistance, these findings underscore the importance of exploring novel therapeutic strategies to safeguard public health.

Introduction

Compounds containing a dimethylaminomethylidene moiety are widely used as platform compounds in the design and creation of new heterocyclic systems possessing both high reactivity and a wide spectrum of biological activity. The presence of several reaction centers, as well as a well-leaving dimethylamino group, determines the synthetic potential of dimethylaminomethylidene derivatives of furan-2(3H)-thiones in transamination reactions involving N-nucleophilic reagents.

Experimental details

The synthesis of 3-[((2-aminophenyl)amino)methylidene]-5-arylfuran-2(3H)-thiones was carried out by the reaction of 3-[(dimethylamino)methylidene]-5-arylfuran-2(3H)-thiones with 1,2 -phenylenediamine in an equimolar ratio when boiling in isopropyl alcohol. Based on IR and NMR spectroscopy data, the structure of the resulting products was established.

Results and Discussion

The synthetic potential of 3-[(dimethylamino)methylidene]-5-arylfuran-2(3H)-thiones in transamination reactions involving an aromatic amine containing an electron-donating substituent, 1,2-phenylenediamine, was studied for the first time. Boiling the reaction mixture in isopropyl alcohol in the absence of a catalyst was chosen as optimal conditions, which made it possible to isolate the final products in high yields. A probable scheme for the occurrence of this interaction is proposed. Using IR spectroscopy, it was found that the final products were isolated in the aminomethylidene tautomeric form. Based on NMR spectroscopy data using a two-dimensional NOESY 2D experiment, it was established that the synthesized 3-[((2-aminophenyl)amino)methylidene]-5-arylfuran-2(3H)-thiones exist in the cis-enamine configuration.

During the last three decades the synthetic utility of indium(III) organometallics and halides have been continuously increased. Indium organometallics (R₃In) have been shown as useful reagents in metal-catalyzed cross-coupling reactions, and indium(III) halides have been shown as efficient π-acids for the electrophilic activation of alkynes towards nucleophilic additions. Furthermore, the application of these methodologies have allowed the synthesis of different natural products and novel organic materials. In this communication we report the synthesis of functionalized BODIPY dyes by palladium-catalyzed cross-coupling reaction with triorganioindum reagents and indium-catalyzed alkyne hydroarylation reactions.

BODIPY derivatives belong to a class of structurally fascinating compounds with interesting fluorescent properties with a wide range of applications.¹ Therefore, the development of new economical and sustainable strategies to functionalized BODIPYs with tunable spectral properties still of current interest. In this endeavor, the synthesis of 2,6-diaryl BODIPYs was achieved through two-fold Pd-catalyzed cross-coupling reaction of 2,6-dihalogenated BODIPys with triarylindium reagents. Likewise, we also found that indium(III)-catalyzed intermolecular double hydroarylation reactions of alkynes with meso-substituted BODIPYs provide a straightforward method for the synthesis of 2,6-dialkenylated BODIPYs in good yields with Markovnikov regioselectivity. Finally, the photophysical properties of the resulting BODIPYs were studied.

References

¹ A. Da Lama, J. Pérez Sestelo, L. A. Sarandeses, M. M. Martínez. J. Org. Chem. 2024, 89, 7402 and references therein.

Acknowledgments

We thank the Ministerio de Ciencia e Innovación−AgenciaEstatal de Investigación (Spain, PID2021-122335NB-I00) and Xunta de Galicia (GRC2022/039) for financial support. ADL thanks Xunta de Galicia for a predoctoral fellowship.

Drugs can be eliminated from the body through two primary mechanisms: metabolization or direct release. This process is dependent on the water solubility of the drug and the type of metabolite generated. The release of unmetabolized drugs has led to a significant environmental impact due to the complex interactions of these compounds with wastewater, leading to their classification as emerging pollutants in ecosystems. To address this issue, we developed a composite material called ZIF-08@BC. This composite is based on cocoa shell biochar (BC) obtained through microwave-assisted pyrolysis, which was then impregnated with an imidazole zeolite-type metal-organic fragment (ZIF-08). The resulting composite material was extensively characterized using various analytical techniques, including TGA, XRD, BET, pH_PZC, and FTIR. The adsorption capacity of the ZIF-08@BC composite was evaluated using the drug loratadine as a model compound. The results showed that the best adsorption process conditions were an adsorbent dose of 0.07 mg/L, pH 6, an initial concentration of 40 mg/L, and a contact time of 40 minutes. Under these conditions, the composite achieved a maximum adsorption capacity of 21.041 mg/g. The adsorption process was found to best fit a pseudo-first-order kinetic model (R² = 0.966, q_e (calc) = 22.46 mg/g, and E = 0.009) and an isothermal Slip model (R² = 0.997 and ks = 0.182). In conclusion, the ZIF-08@BC composite has proven to be an effective adsorbent for the treatment of aqueous media contaminated with the drug loratadine. This composite material represents a promising alternative for mitigating the presence of this emerging contaminant in the environment.

Terpenes and terpenoids are naturally occurring secondary metabolites isolated from plants, which exhibit broad spectrum of biological activity and provide a large library of basic structures for medicinal chemistry. Among this class of substances, camphor and carvone have long been used as starting compounds for the synthesis of new drug candidates. Since natural compounds typically have a complex structure, differing in the hydrocarbon framework and/or the number and position of functional groups, the search for chemo-, stereo- and regioselective methods of transforming native molecules to obtain promising pharmacologically significant analogues is of great importance. To date, numerous derivatives of camphor and carvone have been synthesized, which showed various biological effects.

The present work is aimed at the synthesis of new aryl-substituted propynyl analogues of camphor and carvone as promising building blocks for medicine chemistry. First, alkylation of camphor and carvone with propargyl bromide in the presence of base KN(SiMe₃)₂–Et₃B in 1,2-dimethoxyethane (DME) at room temperature provides 2-propargyl- substituted camphor and carvone derivatives with a yield of 69% and 47%, respectively. Second, the synthesis of aryl-substituted acetylenic monoterpene derivatives with the yield of 70-82% was carried out by the Sonogashira reaction in the presence of PdCl₂(PPh₃)₂, СuI and Et₃N.

Heterocyclic compounds exhibit significant biological activity and play a crucial role in the treatment of various diseases, including diabetes, Alzheimer’s, and cancer. Their diverse structural frameworks allow them to interact with a range of biological targets, making them valuable in drug development. Recent research has demonstrated their potential in developing more effective and targeted therapies for these conditions.

The aim of this study is to synthesize and biologically evaluate a new hybrid heterocyclic derivative for its antioxidant properties. We will investigate its effectiveness in neutralizing free radicals and protecting against oxidative stress. Furthermore, an in-silico study will be conducted to assess the compound's pharmacokinetic (ADMET) properties, evaluating its potential for medicinal applications and therapeutic efficacy.

A new derivative based on quinoléine has been successfully synthesized through a simple condensation reaction without the need for a catalyst, resulting in an excellent yield of 98-90%. These molecules underwent antioxidant testing to demonstrate their antioxidant activity, as well as theoretical simulation studies to verify their anticancer effects.

This study provides evidence that these molecules are significant bioactive compounds with substantial medicinal effects. Their pronounced biological activities highlight their potential as therapeutic agents in the treatment of various diseases. The findings suggest that these compounds could play a crucial role in drug development and offer new avenues for medical research and clinical applications.

Nowadays, one of the most important problems of chemistry is the development and study of new antitumor drugs being able to combine both high efficiency and low toxicity to healthy cells.

Some thiazolo[3,2-a]pyrimidine derivatives showing antitumor and anti-inflammatory activities are already known. Previously, our research group has obtained various thiazolo[3,2-a]pyrimidine derivatives exhibiting high antitumor activity.

Synthesis and study of triazoles is one of the most promising areas in modern organic chemistry. This is due to the great diversity of their properties resulted from their unique structure. 1,2,3-triazoles have high biological activity and are used as drugs.

In this regard, it is of great interest to study compounds containing both thiazolo[3,2-a]pyrimidine and 1,2,3-triazole fragments in their structure.

This work is devoted to the synthesis of triazolyl derivatives based on propargyl ethers of thiazolo[3,2-a]pyrimidine series by [3+2]-cycloaddition and to the study of their structure in solution and in the crystalline phase.

The influence of the solvent on the self-assembly of triazolyl derivatives in the crystalline phase was studied. The formation of homochiral chains or racemic dimers was found to be possible under different conditions. This fact may help to develop a hierarchical approach for fine-tuning of non-covalent interactions to create chiral supramolecular ensembles in the crystalline phase.

As a result, triazolyl derivatives based on thiazolopyrimidine were synthesized. Their structure in solution and in the crystalline phase was studied. The obtained derivatives were characterized by a complex of physicochemical methods (¹H, ¹³C NMR spectroscopy, ESI-MS spectrometry, X-ray diffraction analysis).

Coumarin and its annulated heterocycles are mainly found in natural products, many of that showed significant biological activities and widely used for the preparation of drug molecules. Investigation revealed that many heterocyclic compounds fused with coumarin moiety exhibited antihelmentic, hypnotic, insecticidal, antifungal and anti-coagulant properties. In industry, coumarin scaffolds are widely used for the preparation of pharmaceuticals, agrochemicals, pesticides and dye molecules. In recent studies, several coumarin derivatives have been used in the material science for the preparation of organic cell imaging materials, fluorescent biological probes etc. Due to the immense applications in biological science and materials chemistry field, much attention has been paid by the researchers towards the synthesis of new class of coumarin annulated heterocycles. In this paper, the synthesis of coumarin-annulated polycyclic heterocycles via sequential Claisen rearrangement and tin-hydride mediated radical cyclization has been discussed. The requisite starting materials 3-((4-chlorobut-2-yn-1-yl)oxy)-2H-chromen-2-one (1) was prepared from 3-hydroxycoumarin and 1,4-dichlorobut-2-yne. The Claisen rearrangement of 1 in refluxing chlorobenzene afforded 1-(chloromethyl)pyrano[2,3-c]chromen-5(3H)-one (2). Finally, radical cyclization reactions were carried out smoothly using ⁿBu₃SnH and AIBN in toluene at 110 ^oC, leading to the coumarin-annulated polycyclic heterocycles in high yields. The process is operationally simple and easy to work-up that makes it more convenient for the preparation of coumarin annulated heterocycles.