Organics

18 pages, 13193 KiB

Open AccessArticle

Tannins from Acacia mearnsii De Wild as a Sustainable Alternative for the Development of Latent Fingerprints

by Danielle Tapia Bueno, Amanda Fonseca Leitzke, Rayane Braga Martins, Daisa Hakbart Bonemann, Emanuel Gomes Bertizzolo, Gabrielly Quartieri Sejanes, Juliana Porciúncula da Silva, Lucas Minghini Gonçalves, Neftali Lenin Villarreal Carreno and Claudio Martin Pereira de Pereira

Organics 2025, 6(2), 27; https://doi.org/10.3390/org6020027 - 18 Jun 2025

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Abstract

Papilloscopy, the science of human identification through fingerprints, has seen notable advancements in developing less toxic latent fingerprint developers (LFDs), especially from natural feedstock. Tannins, the second most abundant natural polyphenol, present a potential eco-friendly and cost-effective alternative, with no record of their [...] Read more.

Papilloscopy, the science of human identification through fingerprints, has seen notable advancements in developing less toxic latent fingerprint developers (LFDs), especially from natural feedstock. Tannins, the second most abundant natural polyphenol, present a potential eco-friendly and cost-effective alternative, with no record of their use as LFDs in the existing literature. This study characterized four types of tannins from black wattle, using Fourier Transform Infrared Spectroscopy, revealing key functional groups like C=O, C=C, and O–H. Ultraviolet–visible absorption spectra showed similar behaviors for all tannins, indicating phenolic and benzenoid structures. Energy-dispersive X-ray Spectroscopy identified high concentrations of chlorine, sodium, potassium, and sulfur, naturally found in biomass and soil. Finally, elements in significant concentrations, such as sodium, potassium, iron, zinc, and copper, were found through the incineration of the spent bark. On the basis of these findings, the tannin with the highest potential for LFD was selected. Combining this tannin with spent bark ash resulted in a composite whose performance was evaluated using different methods, including depletion studies, tests with various donors, and assessments on different surfaces. The results demonstrated that this combination significantly enhanced the material’s efficiency by integrating organic and inorganic properties, which improved visual contrast and powder adhesion. Full article

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10 pages, 1754 KiB

Open AccessArticle

A Study of the Inclusion Complex Formed Between Cucurbit[8]uril and N,4-Di(pyridinyl)benzamide Derivative

by Zhikang Wang, Mingjie Yang, Weibo Yang, Zhongzheng Gao, Hui Zhao, Gang Wei and Jifu Sun

Organics 2025, 6(2), 26; https://doi.org/10.3390/org6020026 - 17 Jun 2025

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Abstract

The interaction between cucurbit[8]uril (Q[8]) and the guest 1-methyl-4-(4-(1-methylpyridin-1-ium-4-yl)benzamido)pyridin-1-ium (PB²⁺) has been thoroughly investigated. Multiple techniques were employed, including ¹H NMR spectroscopy, mass spectrometry, isothermal titration calorimetry (ITC), UV–vis absorption spectrophotometry, and quantum chemistry calculations. The experimental results and calculation [...] Read more.

The interaction between cucurbit[8]uril (Q[8]) and the guest 1-methyl-4-(4-(1-methylpyridin-1-ium-4-yl)benzamido)pyridin-1-ium (PB²⁺) has been thoroughly investigated. Multiple techniques were employed, including ¹H NMR spectroscopy, mass spectrometry, isothermal titration calorimetry (ITC), UV–vis absorption spectrophotometry, and quantum chemistry calculations. The experimental results and calculation analysis have clearly shown that in aqueous solution, the host Q[8] preferentially encapsulates the phenylpyridinium salt moiety of the PB²⁺ guest within its hydrophobic cavity, forming a 1:2 inclusion complex. Full article

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11 pages, 2894 KiB

Open AccessArticle

Macrocyclic Azopyrrole: Synthesis, Structure and Fluoride Recognition

by Ying An, Ying Sun and Zhenming Yin

Organics 2025, 6(2), 25; https://doi.org/10.3390/org6020025 - 5 Jun 2025

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Abstract

A macrocyclic receptor based on azopyrrole and polyether was synthesized, and its structure was characterized by NMR (¹H and ¹³C), HRMS and X-ray crystallography. In the solid state, the macrocyclic molecules could bind methanol through a pair of N-H…O hydrogen [...] Read more.

A macrocyclic receptor based on azopyrrole and polyether was synthesized, and its structure was characterized by NMR (¹H and ¹³C), HRMS and X-ray crystallography. In the solid state, the macrocyclic molecules could bind methanol through a pair of N-H…O hydrogen bonds and further self-assembled into tubular structures through C-H…N hydrogen bonds. This revealed that the crystal could still keep its porous properties after the included molecules were removed. The UV–Vis titration indicates that the macrocylic receptor can chromogenically and selectively sense fluoride ion in DMSO solution, and the sensing mechanism was rationalized by ¹H NMR. Full article

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9 pages, 1107 KiB

Open AccessArticle

Efficient Synthesis of Novel 10R-Pyrido[4,3-a]Phenazines, Including the Series Progenitor

by Artem P. Ermolenko, Diana Y. Pobedinskaya, Elena K. Avakyan, Anastasia A. Borovleva, Alexander N. Larin, Ivan V. Borovlev and Oleg P. Demidov

Organics 2025, 6(2), 24; https://doi.org/10.3390/org6020024 - 3 Jun 2025

Viewed by 363

Abstract

A series of previously poorly studied heterocyclic compounds, 10R-pyrido[4,3-a]phenazines, including the previously unknown parent compound, has been synthesized. The proposed synthetic approach is remarkable for its simplicity, due to the ease of the synthesis of the starting materials from readily available precursors, and [...] Read more.

A series of previously poorly studied heterocyclic compounds, 10R-pyrido[4,3-a]phenazines, including the previously unknown parent compound, has been synthesized. The proposed synthetic approach is remarkable for its simplicity, due to the ease of the synthesis of the starting materials from readily available precursors, and is characterized by high yields of the target products, achievable under both acidic and basic catalysis. The paper discusses the synthesis conditions, optimization procedures, and X-ray crystallographic data. Full article

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

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21 pages, 2854 KiB

Open AccessReview

Beyond Peptides and Peptidomimetics: Natural Heteroaromatic Amino Acids in the Synthesis of Fused Heterocyclic Frameworks for Bioactive Agents

by Isis Apolo Silveira de Borba, Jamile Buligon Peripolli, Angélica Rocha Joaquim and Fernando Fumagalli

Organics 2025, 6(2), 23; https://doi.org/10.3390/org6020023 - 21 May 2025

Viewed by 975

Abstract

Heterocycle cores are widely used in medicinal chemistry for developing bioactive compounds. In this scenario, using cheap and accessible starting material to build these heterocycles is desirable to obtain new drug candidates for cost-efficient processes. One easily accessible source of starting material are [...] Read more.

Heterocycle cores are widely used in medicinal chemistry for developing bioactive compounds. In this scenario, using cheap and accessible starting material to build these heterocycles is desirable to obtain new drug candidates for cost-efficient processes. One easily accessible source of starting material are amino acids. Usually, these compounds are employed in peptide synthesis, but their use for building heterocycle frameworks presents another appealing opportunity. Therefore, this review highlights the application of histidine and tryptophan, two heteroaromatic amino acids, in fused heterocyclic scaffold synthesis and their use in bioactive compounds. Full article

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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

Cited by 1 | Viewed by 773

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

Viewed by 604

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

Viewed by 891

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

Cited by 1 | Viewed by 1244

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

Viewed by 717

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

Cited by 1 | Viewed by 559

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

Cited by 1 | Viewed by 3091

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

Viewed by 876

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

Viewed by 658

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

Viewed by 1115

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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Organics, Volume 6, Issue 2 (June 2025) – 15 articles

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