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Organics, Volume 6, Issue 3 (September 2025) – 11 articles

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12 pages, 1579 KB  
Article
Mechanochemical Synthesis, Spectroscopic Characterization and Molecular Structure of Piperidine–Phenytoin Salt
by María Isabel Amil-Miranda, Armando Pineda-Contreras, Francisco Javier Martínez-Martínez, Marcos Flores-Álamo, Hector García-Ortega and Juan Saulo González-González
Organics 2025, 6(3), 38; https://doi.org/10.3390/org6030038 - 22 Aug 2025
Viewed by 86
Abstract
Phenytoin is an anticonvulsant drug that suffers from low aqueous solubility. The formation of phenytoin salts is a strategy employed to address this issue. A phenytoin–piperidine salt (PPD–PNT) was synthesized by solvent-assisted grinding and characterized by infrared (IR) spectroscopy, 1H and 13 [...] Read more.
Phenytoin is an anticonvulsant drug that suffers from low aqueous solubility. The formation of phenytoin salts is a strategy employed to address this issue. A phenytoin–piperidine salt (PPD–PNT) was synthesized by solvent-assisted grinding and characterized by infrared (IR) spectroscopy, 1H and 13C Nuclear Magnetic Resonance (NMR), and powder and single crystal X-ray diffraction. The IR and NMR spectra obtained differed from those of the starting compounds, showing shifts in the N-H and C=O group signals, as well as the appearance of NH+ signals, indicating proton transfer and salt formation. Powder X-ray diffraction confirmed the formation of a new solid phase corresponding to the salt. Single crystal X-ray diffraction showed the molecular structure of the PPD–PNT salt. Full article
(This article belongs to the Special Issue Chemistry of Heterocyclic Compounds)
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20 pages, 2094 KB  
Article
Synthetic Approaches to Steroidal Thiosemicarbazones, 1,3,4-Thia(selena)diazolines, and Oxalate-Linked Dimers
by Luis A. Méndez-Delgado, Mónica Martínez-Montiel, Alma Fuentes-Aguilar, Socorro Meza-Reyes, Sara Montiel-Smith, José Luis Vega-Baez, José M. Padrón and Penélope Merino-Montiel
Organics 2025, 6(3), 37; https://doi.org/10.3390/org6030037 - 22 Aug 2025
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Abstract
A total of 24 novel steroidal derivatives were synthesized, including 1,3,4-thia(selena)diazolines and structurally unique spirothiadiazolines, obtained through intramolecular cyclization under standard acetylation conditions. This strategy was further extended to the construction of a novel dimeric compound bearing a thiadiazoline linker. Seleno- and thiosemicarbazone [...] Read more.
A total of 24 novel steroidal derivatives were synthesized, including 1,3,4-thia(selena)diazolines and structurally unique spirothiadiazolines, obtained through intramolecular cyclization under standard acetylation conditions. This strategy was further extended to the construction of a novel dimeric compound bearing a thiadiazoline linker. Seleno- and thiosemicarbazone precursors were derived from various functionalized steroidal monomers and dimers via straightforward synthetic protocols. Key intermediates included aldehyde 7 and ketones 16, 19, and 24. Rotameric equilibria were observed in certain thiosemicarbazones, attributed to partial double-bond character in the N–CS bond. Cyclization yielded heterocyclic systems as epimeric mixtures, and in some cases, inseparable mixtures of isomers were obtained due to low diastereoselectivity. Full structural elucidation of epimeric pairs was achieved using 2D NMR and IR spectroscopy, with compounds 2, 3, 5, 11, 17, 27, 28a, and 28b further confirmed by single-crystal X-ray diffraction. Preliminary antiproliferative assays against human cancer cell lines revealed GI50 values below 10 µM for compounds 21, 22, and 27. Full article
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13 pages, 3207 KB  
Article
Investigation on Porous Carbon-Loaded MnO for Removing Hexavalent Chromium from Aqueous Solution
by Liping Wang and Mingyu Zhang
Organics 2025, 6(3), 36; https://doi.org/10.3390/org6030036 - 12 Aug 2025
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Abstract
Porous carbon-loaded MnO was prepared via a combination of the sol–gel method and the chemical blow molding method using polyvinylpyrrolidone (PVP) and manganese nitrate as starting materials. SEM, EDX, TEM, FTIR, XRD, XPS, nitrogen adsorption–desorption, and elemental analysis were used to assess its [...] Read more.
Porous carbon-loaded MnO was prepared via a combination of the sol–gel method and the chemical blow molding method using polyvinylpyrrolidone (PVP) and manganese nitrate as starting materials. SEM, EDX, TEM, FTIR, XRD, XPS, nitrogen adsorption–desorption, and elemental analysis were used to assess its physical and chemical characteristics. Furthermore, the adsorption property of porous carbon-loaded MnO for hexavalent chromium (Cr(VI)) in polluted water was investigated in detail. The results demonstrated that large numbers of MnO nanoparticles were evenly mounted on the surfaces of carbon walls, with a uniform distribution of C, N, and O elements. The BET surface area was 46.728 m2/g, and the pore sizes of porous carbon ranged from 2 nm to 10 nm. Additionally, abundant surface functional groups were found in porous carbon-loaded MnO, a result consistent with XPS data and applicable to the adsorption of heavy metals from aqueous solutions containing Cr(VI). The Freundlich model fitted the adsorption isotherm well, and the pseudo−second−order model precisely matched the adsorption kinetics. According to the study results, the adsorption was multilayer, and the adsorption process involved an endothermic reaction. These results indicate that this is a feasible way to synthesize a high−efficiency adsorbent for the removal of harmful heavy−metal ions from wastewater. Full article
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16 pages, 1650 KB  
Article
Profiling of Disubstituted Chloroacetamides’ Potential Biological Activity by Liquid Chromatography
by Suzana Apostolov, Dragana Mekić, Marija Mitrović, Slobodan Petrović and Gyöngyi Vastag
Organics 2025, 6(3), 35; https://doi.org/10.3390/org6030035 - 4 Aug 2025
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Abstract
Modern agriculture relies heavily on the use of pesticides, with one-third of them being herbicides. Chloroacetamides are the most widely used herbicides because of their high effectiveness, but their extensive use poses environmental challenges and threatens the health of living organisms due to [...] Read more.
Modern agriculture relies heavily on the use of pesticides, with one-third of them being herbicides. Chloroacetamides are the most widely used herbicides because of their high effectiveness, but their extensive use poses environmental challenges and threatens the health of living organisms due to toxicity risks. Since the pharmacokinetic behavior and toxicity of a compound are influenced by its lipophilicity, this essential physicochemical parameter for disubstituted chloroacetamides was determined in silico and experimentally through thin-layer chromatography on reversed phases (RPTLC C18/UV254s) in mixtures of water and distinct organic modifiers. The pharmacokinetic profile of chloroacetamides was analyzed by using the BOILED-Egg model. The correlation between the obtained chromatographic parameters and software-based lipophilicity, pharmacokinetic, and ecotoxicity predictors of the studied chloroacetamides was assessed by using linear regression, but more comprehensive insight was obtained through multivariate methods—Cluster Analysis and Principal Component Analysis. It was observed that the total number of carbon atoms in the structure of their molecules, along with the type of hydrocarbon substituents, are the most important factors affecting lipophilicity, pharmacokinetics, and potential toxicity to non-target organisms. Full article
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10 pages, 1360 KB  
Article
Limitations of Frontier Orbital and Charge Approaches in the Description of Electrophilic Aromatic Substitution
by Lucia Emanuele and Maurizio D’Auria
Organics 2025, 6(3), 34; https://doi.org/10.3390/org6030034 - 1 Aug 2025
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Abstract
DFT calculations at the B3LYP/aug-cc-pVDZ level of theory on some aromatic substrates showed that in the HOMO (Highest Occupied Molecular Orbital) of nitrobenzene, the atomic coefficients are not in agreement with the meta-directing behavior of this compound. The atomic coefficients are the same [...] Read more.
DFT calculations at the B3LYP/aug-cc-pVDZ level of theory on some aromatic substrates showed that in the HOMO (Highest Occupied Molecular Orbital) of nitrobenzene, the atomic coefficients are not in agreement with the meta-directing behavior of this compound. The atomic coefficients are the same in the ortho and in the meta positions. The HOMO (or NHOMO (Next Occupied Molecular Orbital) in the case of benzaldehyde) is not in agreement with the experimental results when deactivating, meta-orienting compounds are considered. Mulliken charges sometimes are not able to explain the observed reactivity. Hirshfeld charges allow us to predict the orientation of the attack of an electrophile on the aromatic ring, with the exception of nitrobenzene. Both HOMO atomic coefficients and charges are in agreement with the experimental results when deactivating, ortho-para orienting, and activating compounds are tested. Full article
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21 pages, 3864 KB  
Review
PANI-Based Thermoelectric Materials
by Mengran Chen, Dongmei Xie, Hongqing Zhou and Pengan Zong
Organics 2025, 6(3), 33; https://doi.org/10.3390/org6030033 - 22 Jul 2025
Viewed by 507
Abstract
Polyaniline (PANI) based thermoelectric materials have attracted much attention in flexible energy harvesting devices due to their unique molecular structure, excellent chemical stability, and low cost. However, the intrinsic thermoelectric performance of intrinsic PANI makes it difficult to meet the needs of practical [...] Read more.
Polyaniline (PANI) based thermoelectric materials have attracted much attention in flexible energy harvesting devices due to their unique molecular structure, excellent chemical stability, and low cost. However, the intrinsic thermoelectric performance of intrinsic PANI makes it difficult to meet the needs of practical applications due to its low electronic transport properties. This review focuses on the preparation methods and key strategies for developing high-performance PANI-based thermoelectric materials. It aims to comprehensively update knowledge regarding synthesis methods, microstructures, thermoelectric properties, and underlying mechanisms. The overall goal is to provide timely insights to promote the development of high-performance PANI-based thermoelectric materials. Full article
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35 pages, 7245 KB  
Review
Engineering Nascent Disentangled Ultra-High-Molecular-Weight Polyethylene Based on Heterogeneous Catalytic Polymerization
by Lei Li
Organics 2025, 6(3), 32; https://doi.org/10.3390/org6030032 - 21 Jul 2025
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Abstract
Ultra-high-molecular-weight polyethylene (UHMWPE) is a pivotal material in engineering and biomedical applications due to its exceptional mechanical strength, wear resistance, and impact performance. However, its extreme melt viscosity, caused by extensive chain entanglements, severely limits processability via conventional melt-processing techniques. Recent advances in [...] Read more.
Ultra-high-molecular-weight polyethylene (UHMWPE) is a pivotal material in engineering and biomedical applications due to its exceptional mechanical strength, wear resistance, and impact performance. However, its extreme melt viscosity, caused by extensive chain entanglements, severely limits processability via conventional melt-processing techniques. Recent advances in catalytic synthesis have enabled the production of disentangled UHMWPE (dis-UHMWPE), which exhibits enhanced processability while retaining superior mechanical properties. Notably, heterogeneous catalytic systems, utilizing supported fluorinated bis (phenoxy-imine) titanium (FI) catalysts, polyhedral oligomeric silsesquioxanes (POSS)-modified Z-N catalysts, and other novel catalysts, have emerged as promising solutions, combining structural control with industrial feasibility. Moreover, optimizing polymerization conditions further enhances chain disentanglement while maintaining ultra-high molecular weights. These systems utilize nanoscale supports and ligand engineering to spatially isolate active sites, tailor the chain propagation/crystallization kinetics, and suppress interchain entanglement during polymerization. Furthermore, characterization techniques such as melt rheology and differential scanning calorimetry (DSC) provide critical insights into chain entanglement, revealing distinct reorganization kinetics and bimodal melting behavior in dis-UHMWPE. This development of hybrid catalytic systems opens up new avenues for solid-state processing and industrial-scale production. This review highlights recent advances concerning interaction between catalyst design, polymerization control, and material performance, ultimately unlocking the full potential of UHMWPE for next-generation applications. Full article
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15 pages, 1339 KB  
Article
Synthesis of Cannabigerol and Cannabigerol Derivatives
by Juan F. Ortuño, Alessio Ghisolfi, Raquel Almansa, Olga Soares do Rego Barros, Ana Sirvent, José M. Sansano and Francisco Foubelo
Organics 2025, 6(3), 31; https://doi.org/10.3390/org6030031 - 16 Jul 2025
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Abstract
The synthesis of cannabigerol—a cannabinoid with significant pharmaceutical potential—is described. The synthesis involves four stages. In the first step, (E)-non-3-en-2-one reacts with dimethyl malonate to yield a cyclic enone, which is subsequently oxidized with bromine to produce the olivetol ester. This ester then [...] Read more.
The synthesis of cannabigerol—a cannabinoid with significant pharmaceutical potential—is described. The synthesis involves four stages. In the first step, (E)-non-3-en-2-one reacts with dimethyl malonate to yield a cyclic enone, which is subsequently oxidized with bromine to produce the olivetol ester. This ester then undergoes an alumina-catalyzed coupling reaction with geraniol, followed by ester hydrolysis to obtain cannabigerol. By modifying the chain length of the enone in the initial step and employing allylic alcohols other than geraniol, a range of cannabigerol derivatives can be synthesized, including the natural product cannabigerovarin. Full article
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12 pages, 1949 KB  
Article
Density Functional Theory Study on Mechanism and Selectivity of Nickel-Catalyzed Hydroboration of Vinylarenes
by Jingwei Wu, Yongzhu Zhou, Lei Zhang, Jie Zhang, Pei Song, Xiaoling Wang and Cuihong Wang
Organics 2025, 6(3), 30; https://doi.org/10.3390/org6030030 - 11 Jul 2025
Viewed by 353
Abstract
Density functional theory calculations were performed to elucidate the mechanistic details and origins of the selectivity of the nickel-catalyzed hydroboration of vinylarenes using B2pin2/MeOH. The catalytic cycles involved four sequential elementary steps: hydronickelation, anion exchange, transmetalation, and reductive elimination. [...] Read more.
Density functional theory calculations were performed to elucidate the mechanistic details and origins of the selectivity of the nickel-catalyzed hydroboration of vinylarenes using B2pin2/MeOH. The catalytic cycles involved four sequential elementary steps: hydronickelation, anion exchange, transmetalation, and reductive elimination. Kinetic analyses identified hydronickelation as the rate-determining step with an activation barrier of 19.8 kcal/mol, while transmetalation proceeded through a stepwise mechanism characterized by two distinct transition states. Comprehensive analyses of the relevant transition structures and energetics demonstrated that the observed R-enantioselectivity (94% ee) originated from favorable nonbonding interactions. Lastly, our calculations suggested that the Markovnikov regioselectivity was predominantly governed by steric factors rather than electronic effects. Full article
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23 pages, 3606 KB  
Article
Complementary Synthesis of Anti- and Syn-Hydroxymethyl 1,3-Diols via Regioselective Ring Opening of TIPS-Protected 2,3-Epoxy Alcohols: Toward Polypropionate Fragments
by Raúl R. Rodríguez-Berríos and José A. Prieto
Organics 2025, 6(3), 29; https://doi.org/10.3390/org6030029 - 10 Jul 2025
Viewed by 805
Abstract
Hydroxymethyl 1,3-diol motifs are common structural motifs in natural products, particularly in polypropionates with important therapeutic potential. However, general and complementary methods for their regio- and diastereoselective synthesis remain limited. In this study, we expanded a second-generation epoxide-based methodology involving the regioselective cleavage [...] Read more.
Hydroxymethyl 1,3-diol motifs are common structural motifs in natural products, particularly in polypropionates with important therapeutic potential. However, general and complementary methods for their regio- and diastereoselective synthesis remain limited. In this study, we expanded a second-generation epoxide-based methodology involving the regioselective cleavage of TIPS-monoprotected cis- and trans-2,3-epoxy alcohols using alkenyl Grignard reagents. Regioselective ring opening of cis-epoxides provided anti-1,3-diols, while trans-epoxides afforded the corresponding syn-1,3-diols. The use of cis-propenylmagnesium bromide and vinyl Grignard reagents enabled direct access to cis- and terminal homoallylic 1,3-diols, respectively, with moderate to good yields (46–88%) and excellent regioselectivities (95:5). In contrast, reactions with trans-propenyl Grignard reagent led to partial alkene isomerization, limiting their synthetic utility. To address this, a complementary two-step approach employing propynyl alanate addition followed by sodium/ammonia reduction was incorporated, providing access to trans-homoallylic 1,3-diols with high diastereoselectivity. All 1,3-diols were characterized by NMR spectroscopy, confirming regioselective epoxide opening. These combined strategies offer a practical and modular platform for the synthesis of syn- and anti-hydroxymethylated 1,3-diols and their application to the construction of polypropionate-type fragments, supporting future efforts in the total synthesis of polyketide natural products. Full article
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16 pages, 637 KB  
Review
Structural Innovations in Vancomycin: Overcoming Resistance and Expanding the Antibacterial Spectrum
by Ricardo Cartes-Velásquez, Felipe Morales-León, Franco Valdebenito-Maturana, Pablo Sáez-Riquelme, Nicolás Rodríguez-Ortíz and Hernán Carrillo-Bestagno
Organics 2025, 6(3), 28; https://doi.org/10.3390/org6030028 - 23 Jun 2025
Viewed by 1200
Abstract
Vancomycin, a cornerstone antibiotic against severe Gram-positive infections, is increasingly challenged by resistance in Methicillin-resistant Staphylococcus aureus (MRSA) and Vancomycin Enterococcus spp. (VRE), necessitating the development of novel therapeutic strategies. This review examines how structural modifications to vancomycin can enhance its antibacterial activity [...] Read more.
Vancomycin, a cornerstone antibiotic against severe Gram-positive infections, is increasingly challenged by resistance in Methicillin-resistant Staphylococcus aureus (MRSA) and Vancomycin Enterococcus spp. (VRE), necessitating the development of novel therapeutic strategies. This review examines how structural modifications to vancomycin can enhance its antibacterial activity and explores the critical role of computational approaches in designing the next generation of analogs. By analyzing the existing literature, we highlight how strategic alterations, such as the introduction of lipophilic side chains, substitutions on the sugar moieties, and modifications to the aglycone core, have yielded derivatives with improved antibacterial potency. Notably, certain analogs (e.g., Vanc-83, Dipi-Van-Zn) have demonstrated expanded activity against Gram-negative bacteria and exhibited enhanced pharmacokinetic profiles, including prolonged half-lives and improved tissue penetration, crucial for effective treatment. Semisynthetic glycopeptides like telavancin, dalbavancin, and oritavancin exemplify successful translation of structural modifications, offering sustained plasma concentrations and simplified dosing regimens that improve patient compliance. Complementing these experimental efforts, computational methods, including molecular docking and molecular dynamics simulations, provide valuable insights into drug–target interactions, guiding the rational design of more effective analogs. Furthermore, physiologically based pharmacokinetic modeling aids in predicting the in vivo behavior and optimizing the pharmacokinetic properties of these novel compounds. This review highlights a critical path forward in the fight against multidrug-resistant infections. By meticulously examining the previously carried out structural refinement of vancomycin, guided by computational predictions and validated through rigorous experimental testing, we underscore its immense potential. Full article
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