Organics

22 pages, 3278 KiB

Open AccessReview

Advances in Green Synthesis and Photo-/Electrocatalytic Applications of Zirconium-Based MOFs: A Review

by Tian Zhao, Shilin Peng, Jiangrong Yu, Jiayao Chen, Fuli Luo, Pengcheng Xiao, Saiqun Nie and Yi Chen

Organics 2025, 6(2), 22; https://doi.org/10.3390/org6020022 - 9 May 2025

Abstract

Metal–organic frameworks (MOFs), particularly zirconium-based frameworks (Zr-MOFs), have gained significant attention in recent years due to their unique structural and functional properties. This review focuses on eco-friendly synthetic methods for producing Zr-MOFs, addressing the environmental impacts and costs associated with conventional synthesis, which [...] Read more.

Metal–organic frameworks (MOFs), particularly zirconium-based frameworks (Zr-MOFs), have gained significant attention in recent years due to their unique structural and functional properties. This review focuses on eco-friendly synthetic methods for producing Zr-MOFs, addressing the environmental impacts and costs associated with conventional synthesis, which often relies on hazardous reagents and harsh conditions. We explore various green synthesis strategies, including the selection of raw materials (such as using zirconium acetate), organic ligands (recycling waste materials for ligand synthesis), and synthesis methods (solvothermal, microwave-assisted, ultrasound-assisted, electrochemical, and mechanochemical approaches). Additionally, the application of Zr-MOFs in photocatalysis and electrocatalysis is examined, highlighting their potential for environmental purification and energy conversion. Despite the progress made in laboratory settings, challenges remain in achieving cost-effectiveness, material stability, and scalability for industrial applications. Future research should concentrate on enhancing synthesis efficiency, optimizing catalytic properties, investigating structure–property relationships, and expanding applications to novel catalytic reactions, thus ensuring Zr-MOFs can contribute to sustainable development in chemical science and technology. Full article

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24 pages, 2893 KiB

Open AccessArticle

Adsorption of Methylene Blue Dye onto Various Marine Sediments and Seagrass Biomass of Posidonia oceanica Species: Kinetics and Equilibrium Studies

by Maria C. Vagi, Andreas S. Petsas, Dionysia Dimitropoulou, Melpomeni Leventelli and Anastasia D. Nikolaou

Organics 2025, 6(2), 21; https://doi.org/10.3390/org6020021 - 6 May 2025

Abstract

This study concerns the investigation of the sorption and desorption phenomena of the organic dye methylene blue (MB) on three different marine sediments and non-living biomass of the seagrass species Posidonia oceanica. All tested adsorbents were of natural origin and were collected [...] Read more.

This study concerns the investigation of the sorption and desorption phenomena of the organic dye methylene blue (MB) on three different marine sediments and non-living biomass of the seagrass species Posidonia oceanica. All tested adsorbents were of natural origin and were collected from unpolluted coasts of the North Aegean Sea (Greece). The batch equilibrium technique was applied and MB concentrations were determined by spectrophotochemical analysis (λ = 665 nm). The experimental results showed that all four isotherm models, Freundlich, Langmuir, Henry, and Temkin, could describe the process. The normalized to organic matter content adsorption coefficients (K_OM) ranged between 33.0765 and 34.5279 for the studied sediments. The maximum adsorption capacity (q_max) of sediments was in the range of 0.98 mg g⁻¹ and 6.80 mg g⁻¹, indicating a positive correlation with the adsorbents’ organic matter content, textural analysis of fine fraction (<63 μm), and specific surface area. The bioadsorption of MB on P. oceanica biomass resulted in 13.25 mg g⁻¹ up to 17.86 mg g⁻¹ adsorption efficiency. Desorption studies revealed that the studied dye in most cases was very strongly adsorbed on studied matrices with extremely low quantities of seawater extractable amounts (≤1.62%). According to the experimental findings, phycoremediation by using P. oceanica can be characterized as an efficient method for the bioremediation of dye-polluted wastewater. Full article

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19 pages, 6040 KiB

Open AccessReview

Aniline and Beyond: A Multifaceted Case Study for a Bildung-Focused Chemical Education

by Teresa Celestino

Organics 2025, 6(2), 20; https://doi.org/10.3390/org6020020 - 1 May 2025

Abstract

In the chemical education field, the Johnstone’s triangle represents three learning levels (symbolic, macroscopic, and molecular) needed for students. Afterwards, Mahaffy suggested a tetrahedron model based on this triangle, where the top represents the human element. Subsequently, Sjöström proposed a subdivision of the [...] Read more.

In the chemical education field, the Johnstone’s triangle represents three learning levels (symbolic, macroscopic, and molecular) needed for students. Afterwards, Mahaffy suggested a tetrahedron model based on this triangle, where the top represents the human element. Subsequently, Sjöström proposed a subdivision of the top into three other levels: applied chemistry, socio-cultural context, and critical–philosophic approach. These six dimensions of chemical knowledge will be examined in relation to the discovery of aniline, its chemistry and applications. The historical and epistemic aspects of this topic, gradually broadening the focus to the social, political, and artistic backdrop, can provide a more effective approach to teaching the subject. The major impact of the synthetic dye industry makes this field of study particularly important for a Bildung-focused chemistry education. Full article

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18 pages, 2491 KiB

Open AccessReview

Use and Roles of Tannins in Polysaccharide-Based Bioplastics and Biocomposites

by Carlo Santulli, Serena Gabrielli and Graziella Roselli

Organics 2025, 6(2), 19; https://doi.org/10.3390/org6020019 - 1 May 2025

Abstract

Most bioplastics are based on polysaccharides, which are either synthesized from a variously sourced monomer or extracted from some biomass waste. In many cases, some lignocellulosic fibers are then added to the obtained bioplastics to form biocomposites and extend their range of applications [...] Read more.

Most bioplastics are based on polysaccharides, which are either synthesized from a variously sourced monomer or extracted from some biomass waste. In many cases, some lignocellulosic fibers are then added to the obtained bioplastics to form biocomposites and extend their range of applications beyond packaging films and generically easily biodegradable materials. Plant-extracted tannins, which, as such, might also be building blocks for bioplastics, do nonetheless represent a useful complement in their production when added to polysaccharide-based plastics and biocomposites, since they offer other functions, such as bioadhesion, coloration, and biocidal effect. The variety of species used for tannin extraction and condensation is becoming very wide and is also connected with the local availability of amounts of bio-waste from other productions, such as from the food system. This work tries to summarize the evolution and recent developments in tannin extraction and their increasing centrality in the production of polysaccharide-based plastics, adhesives, and natural fiber composites. Full article

(This article belongs to the Special Issue Chemistry of Heterocyclic Compounds)

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18 pages, 4205 KiB

Open AccessEditor’s ChoiceArticle

Synthesis of Bipyridine Ether-Type Bifunctional Precursors

by Bálint Jávor, Antal Agárdi, Péter Kisfaludi, Barnabás Frigyes, Márton Temesvári, Panna Vezse, Tünde Tóth, Péter Huszthy and Ádám Golcs

Organics 2025, 6(2), 18; https://doi.org/10.3390/org6020018 - 10 Apr 2025

Abstract

Bipyridine ethers are commonly occurring structural motifs in supramolecular chemistry. The herein reported efforts aim to extend the synthetic platform of bipyridino-precursors with new bifunctional intermediates and to improve some previously reported synthetic strategies for structural analogues, like bipyridine-diols as common macrocycle precursors. [...] Read more.

Bipyridine ethers are commonly occurring structural motifs in supramolecular chemistry. The herein reported efforts aim to extend the synthetic platform of bipyridino-precursors with new bifunctional intermediates and to improve some previously reported synthetic strategies for structural analogues, like bipyridine-diols as common macrocycle precursors. In addition, their optimized and highly efficient oxidation to the corresponding dialdehydes is reported to obtain further reactive intermediates with wide modifiability. Furthermore, methylations of pyridine-carbaldehydes were carried out alongside different synthetic strategies to introduce chirality centers. Synthetic difficulties and some unsuccessful approaches are also reported to help in focusing future efforts. Full article

(This article belongs to the Special Issue Chemistry of Heterocyclic Compounds)

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13 pages, 3347 KiB

Open AccessArticle

Small Deviations in Geometries Affect Detonation Velocities and Pressures of Nitroaromatic Molecules

by Danijela S. Kretić, Marija I. Maslarević and Dušan Ž. Veljković

Organics 2025, 6(2), 17; https://doi.org/10.3390/org6020017 - 9 Apr 2025

Abstract

Understanding the factors that affect the detonation performance of high-energy molecules (HEMs) is crucial for the design of novel explosives and fuels with desirable characteristics. While molecular factors, such as the presence of specific functional groups that give organic molecules explosive properties, are [...] Read more.

Understanding the factors that affect the detonation performance of high-energy molecules (HEMs) is crucial for the design of novel explosives and fuels with desirable characteristics. While molecular factors, such as the presence of specific functional groups that give organic molecules explosive properties, are key determinants of detonation characteristics, other factors like the geometry of molecules in crystal structures can also affect the high-energy properties of materials. Although it is known that slight deviations in the crystal structure geometry affect the sensitivity of nitroaromatic explosives, the influence of these variations on detonation performance remains unknown. In this study, we extracted different crystal structures of the same high-energy nitroaromatic molecules from the Cambridge Structural Database and calculated their detonation velocities and pressures using the Kamlet–Jacobs equations. Results indicated that different geometries of the same crystal structure can lead to non-negligible differences in detonation velocities and pressures. In the case of the 2,4,6-triamino-1,3,5-trinitrobenzene molecule, discrepancies in detonation pressures among different crystal structures were calculated to be 7.68%. Analysis of geometrical arrangements showed that these differences are mainly the consequence of diverse non-covalent bonding patterns that affect crystal densities. Full article

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49 pages, 14143 KiB

Open AccessReview

An Overview of Quinolones as Potential Drugs: Synthesis, Reactivity and Biological Activities

by Ayoub El-mrabet, Amal Haoudi, Youssef Kandri-Rodi and Ahmed Mazzah

Organics 2025, 6(2), 16; https://doi.org/10.3390/org6020016 - 3 Apr 2025

Abstract

Quinolones represent one of the largest classes of synthetic antibiotics used in both human and veterinary medicine. Since the discovery of nalidixic acid, a substantial body of research has been carried out on quinolones, resulting in the synthesis of several quinolone derivatives with [...] Read more.

Quinolones represent one of the largest classes of synthetic antibiotics used in both human and veterinary medicine. Since the discovery of nalidixic acid, a substantial body of research has been carried out on quinolones, resulting in the synthesis of several quinolone derivatives with exceptional pharmacology. In addition to their antibacterial action, quinolones have a broad spectrum of diverse biological activities. In this regard, the present review examines the literature of recent years describing synthesis protocols, reactivity and biological properties, with particular emphasis on the antibacterial, antimalarial, antitrypanosomal, antileishmanial, antiviral and anticancer activities of this famous class of molecules. Finally, this review highlights the potential of quinolones as preferred pharmacophores in medicinal chemistry. The aim is to highlight the innovative aspects of the rational design of new therapeutic agents with this structural motif, in the face of emerging antibiotic resistance and the urgent need for new active molecules. Full article

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11 pages, 1186 KiB

Open AccessArticle

Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis

by Marcello Casertano, Brian G. Kelly, Malachi W. Gillick-Healy, Paolo Grieco and Mauro F. A. Adamo

Organics 2025, 6(2), 15; https://doi.org/10.3390/org6020015 - 2 Apr 2025

Abstract

Indole heterocycles have an established reactivity, and these compounds are H-bond donors via a peculiar non-basic NH. However, the indole core has been scarcely employed in organocatalysis, with only a few examples relevant to electrophilic halogenation reported. To expand the range of potential [...] Read more.

Indole heterocycles have an established reactivity, and these compounds are H-bond donors via a peculiar non-basic NH. However, the indole core has been scarcely employed in organocatalysis, with only a few examples relevant to electrophilic halogenation reported. To expand the range of potential transformations achievable via indole catalysis, we have designed a set of new organic species incorporating an indole core, alongside three privelaged chiral moieties found in many known organocatalysts, namely a quaternary ammonium salt, a diamine and an amino-urea. Herein, we report an optimised synthetic route for the preparation of these potential catalytic species in an enantiomerically pure form. The syntheses are conceived to be modular and therefore will allow each of the three single organic catalysts to be expanded into families without alteration of the synthetic layout, therefore leading to a fast optimisation of new asymmetric procedures. Full article

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9 pages, 689 KiB

Open AccessArticle

Optimized Synthesis of Dinitrochalcones via Ultrasonic Bath in a Cyclohexane–Methanol Solvent System

by Alam Yair Hidalgo, Quirino Torres-Sauret, Carlos Ernesto Lobato-García, Erika Madeleyne Ramos-Rivera, Luis Fernando Roa de la Fuente, Abraham Gómez-Rivera, Miguel Ángel Vilchis-Reyes, Erika Alarcón-Matus, Oswaldo Hernández-Abreu and Nancy Romero-Ceronio

Organics 2025, 6(2), 14; https://doi.org/10.3390/org6020014 - 1 Apr 2025

Abstract

This study describes the efficient synthesis of five dinitrochalcones (DNCHs) using an ultrasonic bath as an unconventional method to improve reaction yields and reduce reaction times. The Claisen–Schmidt condensation of nitroacetophenones and nitrobenzaldehydes was carried out in a cyclohexane–methanol solvent system under ultrasonic [...] Read more.

This study describes the efficient synthesis of five dinitrochalcones (DNCHs) using an ultrasonic bath as an unconventional method to improve reaction yields and reduce reaction times. The Claisen–Schmidt condensation of nitroacetophenones and nitrobenzaldehydes was carried out in a cyclohexane–methanol solvent system under ultrasonic irradiation, achieving yields between 56% and 92%. The application of ultrasound not only accelerated the reaction but also improved the overall efficiency compared to conventional methods such as magnetic stirring. The synthesized compounds were characterized by NMR spectroscopy, which corroborated their structures. Therefore, it is confirmed that obtaining DNCHs with a nitro group in ortho by ultrasonic irradiation is an energetically efficient and environmentally friendly alternative. Full article

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26 pages, 8018 KiB

Open AccessArticle

Synthesis and In Silico Evaluation of GABA, Pregabalin and Baclofen N-Heterocyclic Analogues as GABA_B Receptor Agonists

by Zuleyma Martínez-Campos, Luis Eduardo Hernandez-Dominguez, Fatima Romero-Rivera, Diana López-López, María Vicky Corona-González, Susana T. López-Cortina, Francisco José Palacios-Can, Rodrigo Said Razo-Hernández and Mario Fernández-Zertuche

Organics 2025, 6(2), 13; https://doi.org/10.3390/org6020013 - 24 Mar 2025

Abstract

γ-amino butyric acid (GABA) is an inhibitory neurotransmitter whose deficiency has been associated with various neurological disorders. However, its low liposolubility limits its use as a supplement. Thus, multiple investigations have focused on searching for lipophilic GABA analogs that can modulate the [...] Read more.

γ-amino butyric acid (GABA) is an inhibitory neurotransmitter whose deficiency has been associated with various neurological disorders. However, its low liposolubility limits its use as a supplement. Thus, multiple investigations have focused on searching for lipophilic GABA analogs that can modulate the activity of the GABA_B receptor, which could be associated with the etiology of some central nervous system disorders. The GABA analogs available on the market are Vigabatrin, Gabapentin as well as Pregabalin and Baclofen. In this work, we report on the synthesis of GABA analogs, taking the scaffold of GABA, Pregabalin, and Baclofen as a starting point. The analogs include structural features that could favor the affinity of the molecules for the GABA_B receptor, such as heterocyclic rings in the γ-position and alkyl or p-Cl-phenyl substituents (in analogy to Pregabalin and Baclofen, respectively). These analogs were synthesized by a sequence of reactions involving an N-alkylation, a 1,4-conjugated addition of dialkyl and diarylcuprates and a basic hydrolysis. Furthermore, a computational molecular docking over the GABA_B receptor was performed to evaluate the interaction of each compound in the Baclofen binding site. With this information, we evaluated our compounds as GABA_B agonists through a QSAR analysis. Finally, by means of molecular similarity analysis, and in silico ADME prediction, we support our three best compounds (8a–b, 8d) as potential GABA_B receptor agonists. Full article

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13 pages, 4529 KiB

Open AccessArticle

Graft Reaction of Furfural with Polyvinyl Chloride and Its Effect on Thermal Stability of Polyvinyl Chloride

by Mengying Kou and Kanshe Li

Organics 2025, 6(1), 12; https://doi.org/10.3390/org6010012 - 4 Mar 2025

Abstract

A graft reaction of polyvinyl chloride (PVC) with furfural was conducted in a tetrahydrofuran solution. The resulting graft structure (FF-g-PVC) was characterized using UV spectroscopy, photoluminescence (PL), Fourier Transform Infrared (FTIR) spectroscopy, Raman spectroscopy, and proton nuclear magnetic resonance (¹H NMR) [...] Read more.

A graft reaction of polyvinyl chloride (PVC) with furfural was conducted in a tetrahydrofuran solution. The resulting graft structure (FF-g-PVC) was characterized using UV spectroscopy, photoluminescence (PL), Fourier Transform Infrared (FTIR) spectroscopy, Raman spectroscopy, and proton nuclear magnetic resonance (¹H NMR) spectroscopy. The grafting efficiency was determined through ultraviolet spectrophotometry. Thermal stability analysis via thermogravimetric (TG) testing revealed that furfural was successfully grafted onto the PVC chain. In a nitrogen atmosphere, the temperature of the maximum weight loss rate during the first stage of pyrolysis increased from 296.3 °C to 301.7 °C, while the activation energy for the second stage increased from 199.4 kJ/mol to 294.4 kJ/mol, indicating enhanced stability and delayed degradation of the PVC. Additionally, microwave irradiation markedly improved the graft reaction, achieving a grafting rate of 57.76‰ compared to only 1.808‰ with water bath heating. The optimal conditions were found to be a PVC/FF/Zn ratio of 1:1:0.9, with microwave irradiation for 20 min at 40 °C. Full article

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14 pages, 9759 KiB

Open AccessArticle

Synthesis and Biological Evaluation of Salicylaldehyde-Derived Secondary Amines: Antioxidant, Anti-Inflammatory, and Insecticidal Activities with DFT Insights

by Chamseddine Derabli, Noureddine Rahim, Roumaissa Djaba, Sarra Aouidi, Chawki Bensouici, Stephanie Hesse and Houssem Boulebd

Organics 2025, 6(1), 11; https://doi.org/10.3390/org6010011 - 3 Mar 2025

Abstract

Six secondary amine derivatives derived from salicylaldehyde (SA) were successfully synthesized in good to excellent yields and evaluated for their biological activities. The synthesized compounds exhibited remarkable antioxidant properties, as determined by ABTS and phenanthroline assays. Notably, compound 2 demonstrated an IC₅₀ [...] Read more.

Six secondary amine derivatives derived from salicylaldehyde (SA) were successfully synthesized in good to excellent yields and evaluated for their biological activities. The synthesized compounds exhibited remarkable antioxidant properties, as determined by ABTS and phenanthroline assays. Notably, compound 2 demonstrated an IC₅₀ value of 5.14 ± 0.11 µM in the ABTS assay, approximately six to nine times lower than the standards BHT and BHA. In the phenanthroline assay, all compounds showed inhibition capacities five to ten times greater than BHT and comparable to BHA, with A_0.5 values ranging from 9.42 to 31.73 µM. Among these, compound 5 displayed the lowest A_0.5 value of 9.42 ± 1.02 µM. The anti-inflammatory activity, assessed through BSA denaturation, revealed that compounds 2 and 5 were the most promising, although their activity was moderate compared to the standard diclofenac. The insecticidal potential of the compounds was evaluated against the storage insect pest Tribolium castaneum. Among the tested derivatives, compounds 1 and 6 exhibited the highest efficacy, achieving maximum mortality rates of 73.31% and 76.67%, respectively, over a seven-day treatment period. Furthermore, the molecular geometry, electronic properties, and intramolecular interactions of all compounds were investigated using DFT calculations. Thermodynamic analyses of the antioxidant mechanisms suggested that the NH bond is the most likely site for free radical attacks. These findings underscore the significant biological potential of the synthesized salicylaldehyde-derived secondary amines. Full article

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16 pages, 3593 KiB

Open AccessArticle

Luminescence of the Conjugate Bases of [2-(2-Hydroxyphenyl)phenyl]phosphinic Acid and Single-Crystal X-Ray Structure Determination of Sodium [2-(2-Hydroxyphenyl)phenyl]phosphinate

by Valeria Gagliardi, Jesús Castro, Valentina Beghetto, María Expósito and Marco Bortoluzzi

Organics 2025, 6(1), 10; https://doi.org/10.3390/org6010010 - 3 Mar 2025

Abstract

The commercial flame-retardant 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) was almost quantitatively converted in sodium [2-(2-hydroxyphenyl)phenyl]phosphinate Na[OH-Ph-Ph-PHO₂] and disodium 2-(2-phosphinatophenyl)benzen-1-olate Na₂[O-Ph-Ph-PHO₂] under mild reaction conditions and without the use of toxic reactants. The structure of Na[OH-Ph-Ph-PHO₂] was determined by [...] Read more.

The commercial flame-retardant 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) was almost quantitatively converted in sodium [2-(2-hydroxyphenyl)phenyl]phosphinate Na[OH-Ph-Ph-PHO₂] and disodium 2-(2-phosphinatophenyl)benzen-1-olate Na₂[O-Ph-Ph-PHO₂] under mild reaction conditions and without the use of toxic reactants. The structure of Na[OH-Ph-Ph-PHO₂] was determined by means of single-crystal X-ray diffraction. The inter- and intramolecular Na-O interactions generate a stair-like framework where the sodium cations are five-coordinated and exhibit a highly distorted coordination sphere. The two compounds are characterized by appreciable blue luminescence at the solid state upon excitation with UV light, attributed to S₁→S₀ decays on the basis of time-resolved measurements and computational calculations. The photoluminescence quantum yield is higher for Na₂[O-Ph-Ph-PHO₂], and the emission and excitation bands are shifted at longer wavelengths. The disodium salt showed affinity towards cellulose, and doped Na₂[O-Ph-Ph-PHO₂]@cellulose samples maintained emission features comparable to those of the pure compound. The nature of the interaction between cellulose and the emitting species was studied by means of periodic density functional theory calculations, that highlighted the role of the sodium cations. Full article

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11 pages, 2298 KiB

Open AccessArticle

Photochemical Acylation of 1,4-Naphthoquinone with Aldehydes Under Continuous-Flow Conditions

by Madyan A. Yaseen and Michael Oelgemöller

Organics 2025, 6(1), 9; https://doi.org/10.3390/org6010009 - 14 Feb 2025

Abstract

A series of photoacylations of 1,4-naphthoquinone with various aldehydes and using Pyrex-filtered UVB light was conducted under continuous-flow conditions. Acetone served as a triplet photosensitizer and convenient solvent that kept all materials in solution and could be easily removed. The corresponding acylated 1,4-naphthohydroquinone [...] Read more.

A series of photoacylations of 1,4-naphthoquinone with various aldehydes and using Pyrex-filtered UVB light was conducted under continuous-flow conditions. Acetone served as a triplet photosensitizer and convenient solvent that kept all materials in solution and could be easily removed. The corresponding acylated 1,4-naphthohydroquinone photoproducts were obtained in acceptable to excellent yields of 30–90% with residence times of just 70 min. The photoacylation process was successfully coupled with in-line oxidation to obtain acylated 1,4-naphthoquinones. Full article

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18 pages, 4225 KiB

Open AccessArticle

Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate

by Amanda Neves de Souza, Adriano Monteiro de Castro Pimenta and Rodrigo Moreira Verly

Organics 2025, 6(1), 8; https://doi.org/10.3390/org6010008 - 11 Feb 2025

Cited by 1

Abstract

Bioactive peptides are promising therapeutic agents due to their antimicrobial and anticancer activities, although their lack of selectivity often limits clinical applications. This study demonstrates the optimal synthetic route for conjugating folic acid (FA) with the bioactive peptide Lunatin-1, aiming to improve selectivity [...] Read more.

Bioactive peptides are promising therapeutic agents due to their antimicrobial and anticancer activities, although their lack of selectivity often limits clinical applications. This study demonstrates the optimal synthetic route for conjugating folic acid (FA) with the bioactive peptide Lunatin-1, aiming to improve selectivity for neoplastic cells. The synthesis combines solid-phase peptide synthesis (SPPS) and Cu(I)-catalyzed cycloaddition to link folic acid to Lunatin-1 via a triazole ring. Using the model tripeptide FIG-_NH2, key intermediates and the final product were characterized by high-performance liquid chromatography (HPLC), mass spectrometry (MALDI-ToF), Fourier-transform infrared spectroscopy (FTIR), and nuclear magnetic resonance (NMR). Reaction yields and purity were optimized with FIG-_NH2, providing a reproducible synthesis pathway. Additionally, the results confirmed successful conjugation, with the FA-Trz-Luna product exhibiting molecular integrity and structural stability, as validated by spectral analyses. This study highlights a potential synthesis route for peptide-folate conjugates to be used as selective and multifunctional therapeutic agents, laying the groundwork for biological evaluations of their cytotoxicity and antimicrobial properties. Full article

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16 pages, 2219 KiB

Open AccessArticle

Synthesis of Bispidine-Based Prostate-Specific Membrane Antigen-Targeted Conjugate and Initial Investigations

by Aleksei E. Machulkin, Stanislav A. Petrov, Maria D. Kraynova, Anastasiia S. Garanina, Bayirta V. Egorova, Roman V. Timoshenko, Alexander N. Vaneev, Alexander S. Erofeev, Anna B. Priselkova, Mikhail A. Kalinin, Aleksei V. Medved′ko, Stepan N. Kalmykov, Elena K. Beloglazkina and Sergey Z. Vatsadze

Organics 2025, 6(1), 7; https://doi.org/10.3390/org6010007 - 10 Feb 2025

Abstract

Nowadays, PSMA ligands are widely used for radiotheragnostic purposes in prostate cancer. The synthesis of a PSMA-Bisp conjugate was developed and realized with good yield (overall yield ~58% for the last two steps). All newly synthesized compounds were characterized by physicochemical methods: ¹ [...] Read more.

Nowadays, PSMA ligands are widely used for radiotheragnostic purposes in prostate cancer. The synthesis of a PSMA-Bisp conjugate was developed and realized with good yield (overall yield ~58% for the last two steps). All newly synthesized compounds were characterized by physicochemical methods: ¹H and ¹³C NMR, HRMS, and LCMS (for biologically tested samples). Subsequently, Bisp1 (diacetate bispidine ligand), Bisp-alkyne (bifunctional derivative of Bisp1), and its conjugate PSMA-Bisp were labeled by ⁶⁴Cu in mild conditions. In vitro studies of the labeled conjugate [⁶⁴Cu]Cu-PSMA-Bisp have shown great stability in model solutions. Finally, [⁶⁴Cu]Cu-PSMA-Bisp was compared to the well-known PSMA-617 conjugate labeled with ⁶⁴Cu and they showed similar stability in excess bovine serum (BVS), and at the same time, labeling PSMA-Bisp with ⁶⁴Cu is characterized by extremely high kinetics in mild conditions, while labeling PSMA-617 with ⁶⁴Cu requires heating (90 °C). Thus, this conjugate can be incredibly promising for nuclear medicine. Full article

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11 pages, 2180 KiB

Open AccessArticle

Facile Synthesis of a Cholesterol–Doxorubicin Conjugate Using Cholesteryl-4-nitrophenolate as an Activated Ester and Biological Property Analysis

by Pedro Freitas, Dina Maciel, Jolanta Jaśkowska, Kamila Zeńczak-Tomera, Yanbiao Zhou, Guoyin Yin and Ruilong Sheng

Organics 2025, 6(1), 6; https://doi.org/10.3390/org6010006 - 9 Feb 2025

Abstract

Developing new biomolecule–drug conjugates as prodrugs is a promising area for natural products and pharmaceutical chemistry. Herein, a cholesterol–doxorubicin (Chol-DOX) conjugate was synthesized using cholesteryl-4-nitrophenolate as a facile, stable, and controllable activated ester. This approach offers an alternative to the conventional HCl-emitting cholesteryl [...] Read more.

Developing new biomolecule–drug conjugates as prodrugs is a promising area for natural products and pharmaceutical chemistry. Herein, a cholesterol–doxorubicin (Chol-DOX) conjugate was synthesized using cholesteryl-4-nitrophenolate as a facile, stable, and controllable activated ester. This approach offers an alternative to the conventional HCl-emitting cholesteryl chloroformate method. Semi-empirical theoretical calculations showed that cholesteryl-4-nitrophenolate exhibits moderate reactivity, greater thermodynamic stability, a higher dipole moment, and a lower HOMO-LUMO energy gap compared to cholesteryl chloroformate, suggesting that cholesteryl-4-nitrophenolate could be used as a more controllable acylating agent. The structure of the synthesized Chol-DOX conjugate was characterized using NMR, MS, and FT-IR techniques. Biological properties of the Chol-DOX conjugate were analyzed with a comparison of theoretical and experimental data. This work provides a facile and controllable method to synthesize natural lipid–DOX prodrugs and offers an in-depth data analysis of the related biological properties. Full article

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11 pages, 1336 KiB

Open AccessArticle

Vinylation of Alcohols, Thiols, and Nitrogen Compounds Using a Stoichiometric Amount of In Situ Generated Acetylene

by Maria S. Ledovskaya, Vladimir V. Voronin, Anna A. Reznichenko and Ekaterina A. Reznichenko

Organics 2025, 6(1), 5; https://doi.org/10.3390/org6010005 - 8 Feb 2025

Abstract

In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of a broad scope of substances, including alcohols, thiols, and nitrogen compounds. The key advantage of the proposed method is the use of calcium carbide as a [...] Read more.

In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of a broad scope of substances, including alcohols, thiols, and nitrogen compounds. The key advantage of the proposed method is the use of calcium carbide as a robust acetylene source in a stoichiometric ratio to the substrates. Lacking the requirement of acetylene excess, the developed protocol is safe, highly economic, and limits waste production. The procedure allows for a large variety of O-,S-,N-vinyl compounds to be synthesized in up to quantitative yields. Our methodology is scalable, allowing us to obtain vinyl derivatives in Gram-scale quantities. We also demonstrated the significant synthetic value of our approach by performing a label-economic synthesis of ¹³C₂-labeled vinyl derivatives using calcium carbide-¹³C₂. In our well-optimized process, the conversion of Ca¹³C₂ reached 89%. Full article

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17 pages, 2664 KiB

Open AccessReview

Ferrocene Derivatives as Histone Deacetylase Inhibitors: Synthesis and Biological Evaluation

by Rostislava Angelova and Georgi Stavrakov

Organics 2025, 6(1), 4; https://doi.org/10.3390/org6010004 - 26 Jan 2025

Abstract

Ferrocene is an organometallic compound that has attracted considerable scientific interest due to its unique properties, including low toxicity, excellent stability in aqueous and aerobic media, and high lipophilicity, which enhances membrane permeability. The ferrocene moiety has been effectively used as a bioisostere [...] Read more.

Ferrocene is an organometallic compound that has attracted considerable scientific interest due to its unique properties, including low toxicity, excellent stability in aqueous and aerobic media, and high lipophilicity, which enhances membrane permeability. The ferrocene moiety has been effectively used as a bioisostere of phenyl rings and heteroaromatic groups in the structures of approved tyrosine kinase inhibitors and histone deacetylase inhibitors (HDACis). HDACis exert their cytotoxic effects by blocking cyclin/CDK complexes, causing cell cycle arrest, inducing apoptosis, inhibiting angiogenesis, and through non-histone-directed mechanisms. This mini-review summarizes the synthesis and biological evaluation of small libraries of compounds in which a ferrocenyl moiety is incorporated into the structure of suberoylanilide hydroxamic acid (SAHA) and a number of analogues. The influence of the organometallic function on the antiproliferative effect is investigated. Both docking analysis and in vitro studies confirm that the ferrocenyl-modified HDACis exhibit potent cytotoxicity and strong inhibitory activity against the various enzyme isoforms. Full article

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Organics

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