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19 pages, 662 KiB

Open AccessArticle

Microwave-Assisted Synthesis, Lipophilicity and In Vitro Antimicrobial Activity of Hydrazide-Hydrazones of Phenylacetic Acid

by Magda Kuć, Anna Berecka-Rycerz, Anna Biernasiuk and Łukasz Popiołek

Appl. Sci. 2025, 15(7), 3436; https://doi.org/10.3390/app15073436 - 21 Mar 2025

Viewed by 267

Abstract

Microwave-assisted synthesis was applied to obtain fifteen hydrazide-hydrazones of phenylacetic acid. The chemical structure of the synthesized compounds was confirmed on the basis of the analysis of the IR, ¹H NMR and ¹³C NMR spectra. Experimental logP values for all obtained [...] Read more.

Microwave-assisted synthesis was applied to obtain fifteen hydrazide-hydrazones of phenylacetic acid. The chemical structure of the synthesized compounds was confirmed on the basis of the analysis of the IR, ¹H NMR and ¹³C NMR spectra. Experimental logP values for all obtained acylhydrazones were established with the use of chromatographic methods. The synthesized compounds were tested for potential antimicrobial activity in in vitro conditions against a panel of microorganisms, which included eight strains of Gram-positive bacteria and six strains of Gram-negative bacteria as well as six strains of yeasts belonging to Candida spp. The assays we performed revealed significant antibacterial activity of obtained hydrazide-hydrazones of phenylacetic acid. Some of the tested compounds possessed much higher activity than that of reference antimicrobial agents towards Gram-positive bacterial strains. It is also worth mentioning that some of synthesized compounds possessed significant activity towards MRSA strain—methicillin-resistant Staphylococcus aureus ATCC 43300 and MSSA strain—methicillin susceptible Staphylococcus aureus ATCC 6538 and ATCC 29213. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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29 pages, 9558 KiB

Open AccessArticle

Revitalizing Recovery: Unveiling the Potential of Apigenin and Related Flavonoids in Long COVID-19 Therapy Through Molecular Dynamics Simulation

by Muchtaridi Muchtaridi, Riska Prasetiawati, Siti Ajah Alawiah, Shela Salsabila, Taufik Muhammad Fakih, Rina Fajri Nuwarda and Nur Kusaira Khairul Ikram

Appl. Sci. 2025, 15(3), 1493; https://doi.org/10.3390/app15031493 - 1 Feb 2025

Viewed by 1365

Abstract

Long COVID-19, also known as post-acute sequelae of SARS-CoV-2 infection (PASC), involves symptoms or effects that persist for more than 4 weeks after the initial SARS-CoV-2 infection. One contributing factor to this condition is the disruption in the expression of the antioxidant enzyme [...] Read more.

Long COVID-19, also known as post-acute sequelae of SARS-CoV-2 infection (PASC), involves symptoms or effects that persist for more than 4 weeks after the initial SARS-CoV-2 infection. One contributing factor to this condition is the disruption in the expression of the antioxidant enzyme Nuclear Factor Erythroid-2 (Nrf2) induced by the COVID-19 infection. Apigenin and related flavonoids, known for their diverse pharmacological activities, including potent antioxidant properties, have emerged as promising candidates for Long COVID-19 therapy. These compounds, particularly apigenin, are recognized for their ability to modulate oxidative stress and inflammation, making them potential activators of the Nrf2 pathway. This study aims to predict the activity of apigenin and its related flavonoids as Nrf2 activators using molecular modeling and molecular dynamics (MD) techniques, providing insights into their therapeutic potential in managing Long COVID-19. The findings from the molecular modeling analysis indicate that apigenin has a favorable affinity, with a free energy value (ΔG) of −6.40 kcal/mol. Additionally, MD simulation results demonstrate the strong stability of the Keap1-apigenin complex, with an average Root Mean Square Deviation (RMSD) value below 0.20 nm and the lowest average Root Mean Square Fluctuation (RMSF) value of 0.86 nm. Using the Molecular Mechanics/Generalized Born Surface Area (MM-GBSA) calculation method, the binding affinity of the Keap1-apigenin complex yields a lower free energy value (ΔG) of −67.039 kJ/mol, consistent with the molecular modeling results. Apigenin also exhibits the ability to inhibit the binding of Nrf2 to the hydrophobic surface of Keap1, with a total energy value of 993.266 kcal/mol and binding affinity value of −1.162 kJ/mol through peptide−receptor docking. In conclusion, the comprehensive results suggest that apigenin has the potential to be a lead compound for developing Nrf2 activators specifically designed for Long COVID-19 therapy. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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12 pages, 1211 KiB

Open AccessArticle

Regioselective De Novo Synthesis of Phenolic Isoprenoids Grifolin and Neogrifolin

by Boram Lim, Huisu Yeo, Seunghyo Han, Dabin Kim, Hansuk Lee and Sangho Koo

Appl. Sci. 2025, 15(3), 1438; https://doi.org/10.3390/app15031438 - 30 Jan 2025

Viewed by 669

Abstract

The total synthesis of biologically and pharmacologically important phenolic isoprenoids, grifolin and neogrifolin, was developed through simple allylation and cyclization procedures using only ethyl acetoacetate, ethyl crotonate, and farnesyl bromide as substrates. The regioisomeric terpenophenols, which consist solely of orcinol and farnesyl moieties, [...] Read more.

The total synthesis of biologically and pharmacologically important phenolic isoprenoids, grifolin and neogrifolin, was developed through simple allylation and cyclization procedures using only ethyl acetoacetate, ethyl crotonate, and farnesyl bromide as substrates. The regioisomeric terpenophenols, which consist solely of orcinol and farnesyl moieties, cannot be synthesized purely by direct coupling between the units. The regioselectivity issue was solved by controlling the timing of the allylation of β-ketoester with farnesyl bromide and the cyclization with ethyl crotonate. 2-Farnesyl-5-methyl-cyclohexane-1,3-dione and 6-farnesyl-5-methyl-cyclohexane-1,3-dione were prepared in a highly regioselective manner from ethyl acetoacetate in overall yields of 43% and 40%, respectively. The oxidative aromatization of the regioisomeric cyclohexane-1,3-diones produced grifolin and neogrifolin, respectively. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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21 pages, 49290 KiB

Open AccessArticle

New Steroid–Alkaloid Bioconjugates as Potential Bioactive Compounds: Synthesis, Spectroscopic and In Silico Study

by Hanna Koenig, Karolina Babijczuk, Kamil Ostrowski, Damian Nowak, Tomasz Pospieszny and Beata Jasiewicz

Appl. Sci. 2025, 15(2), 591; https://doi.org/10.3390/app15020591 - 9 Jan 2025

Viewed by 816

Abstract

The search for new biologically active compounds with prospective pharmaceutical applications has motivated the investigation of alternative synthesis pathways. One such approach involves the development of compounds with established biological activity as lead compounds. The focus on compounds of natural origin is gaining [...] Read more.

The search for new biologically active compounds with prospective pharmaceutical applications has motivated the investigation of alternative synthesis pathways. One such approach involves the development of compounds with established biological activity as lead compounds. The focus on compounds of natural origin is gaining prominence, with steroids and alkaloids representing notable examples. Our research aimed to synthesize novel steroid–alkaloid bioconjugates with potential biological activity. The structure of all new compounds was determined using spectroscopic methods. The final heats of formation (HOF) for all bioconjugates were also calculated. In silico methods demonstrated that most obtained compounds, especially caffeine derivatives, exhibited potential biological activity. These compounds act as cholesterol antagonists, analeptics, antihypercholesterolemic, and respiratory analeptic compounds. The molecular docking results for the 1HWK and 6RZ4 protein domains indicate that the selected bioconjugates exhibit affinities comparable to or lower than those of atorvastatin (−9.6 kcal/mol), the reference ligand in cholesterol-lowering. Conversely, the affinities of the selected bioconjugates are higher than those of caffeine (−6.2 kcal/mol), which is used as the reference ligand for analeptic drugs. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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16 pages, 1620 KiB

Open AccessArticle

Application of a Validated HPLC Method for the Determination of Resveratrol, Ferulic Acid, Quercetin, Retinol, and α-Tocopherol in a Cold Cream—Permeability Study

by Athanasia Karavalasi, Sofia Almpani, Panagiota Tserkezou, Konstantina Chachlioutaki, Georgios Kamaris and Catherine K. Markopoulou

Appl. Sci. 2024, 14(24), 11843; https://doi.org/10.3390/app142411843 - 18 Dec 2024

Viewed by 1375

Abstract

Due to the rapid increase in the use of anti-aging cosmetic products, there is a need to develop valid analytical methods to control their quality. The present work deals with the development and validation of a new chromatographic method for the quantitative determination [...] Read more.

Due to the rapid increase in the use of anti-aging cosmetic products, there is a need to develop valid analytical methods to control their quality. The present work deals with the development and validation of a new chromatographic method for the quantitative determination of five lipophilic components (resveratrol, ferulic acid, quercetin, retinol, and α-tocopherol), with anti-aging properties, in a cold cream (w/o). For the HPLC-UV separation of the active ingredients, an HS, Discovery^® Supelco (Supelco Inc., Bellefonte, PA, USA), C₁₈ column (25 cm × 4.6 mm), 5 μm (at 40 °C) was used as a stationary phase while a binary system of A: Acetonitrile with formic acid 0.2% and B: H₂O with formic acid 0.2%, in gradient elution (flow 1.5 mL·min⁻¹), was used as mobile. The analytical method was validated according to ICH guidelines Q2(R2), where linearity (r² ≥ 0.998), selectivity, precision (% recovery 97.1–101.9), and accuracy (%RSD < 2) were evaluated. The processing of the samples for the recovery of the five analytes from the cream was investigated by experimental design methodology and the cross D-optimal technique (% recovery 98.5–102.9, %RSD < 2%, n = 5). Finally, the same analysis was applied to study the transdermal penetration of the active ingredients incorporated in cold cream (over a period of 8 h). Their behavior was compared with the corresponding one in suspension using Franz cells in a vertical arrangement. The new method is considered reliable for the analysis of the anti-aging product. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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18 pages, 1369 KiB

Open AccessArticle

Synthesis and In Vitro Anticancer Activity of Pyrrolidone Derivatives Bearing 3,4,5-Trimethoxyphenyl Moiety as a Promising Anticancer Scaffold

by Povilas Kavaliauskas, Birutė Sapijanskaitė-Banevič, Birutė Grybaitė, Eglė Mickevičiūtė, Kazimieras Anusevičius, Andrew Garcia, Ethan Naing, Rūta Petraitienė, Vidmantas Petraitis, Ramunė Grigalevičiūtė and Vytautas Mickevičius

Appl. Sci. 2024, 14(24), 11784; https://doi.org/10.3390/app142411784 - 17 Dec 2024

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Abstract

A series of 5-oxo-1-(3,4,5-trimethoxyphenyl)pyrrolidine-3-carboxylic acid derivatives–hydrazones, N-ethylhydrazones, pyrrole, pyrazole, oxadiazole, and triazole were synthesized and evaluated for their anticancer activity using human A549 pulmonary epithelial cells (ATCC CCl-185). The in vitro viability inhibitory effects of the compounds were assessed using the MTT [...] Read more.

A series of 5-oxo-1-(3,4,5-trimethoxyphenyl)pyrrolidine-3-carboxylic acid derivatives–hydrazones, N-ethylhydrazones, pyrrole, pyrazole, oxadiazole, and triazole were synthesized and evaluated for their anticancer activity using human A549 pulmonary epithelial cells (ATCC CCl-185). The in vitro viability inhibitory effects of the compounds were assessed using the MTT assay. The characterization of the anticancer activity of the synthesized compounds showed that the incorporation of 1,3,4-oxadiazolethione and 4-aminotriazolethione rings into the molecular structures obviously enhances the anticancer activity against human A549 lung epithelial cells, reducing their viability to 28.0% and 29.6%, respectively. The anticancer activity of these azole derivatives was significantly higher than that of cytarabine. Further studies are needed to better optimize 5-oxo-1-(3,4,5-trimethoxyphenyl)pyrrolidine-3-carboxylic acid derivatives and enhance their in vitro anticancer activity. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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28 pages, 15959 KiB

Open AccessArticle

Box–Behnken Design-Based Optimization of Extraction Parameters of Phenolics, Antioxidant Activity, and In Vitro Bioactive and Cytotoxic Properties of Rhus typhina Fruits

by Maria Denisa Cocîrlea, Natalia Simionescu, Teodora Călin, Florentina Gatea, Georgiana Ileana Badea, Emanuel Vamanu and Simona Oancea

Appl. Sci. 2024, 14(23), 11096; https://doi.org/10.3390/app142311096 - 28 Nov 2024

Cited by 1 | Viewed by 1203

Abstract

Rhus typhina, an invasive plant species, contains valuable compounds that can be utilized in various fields. The main aim of this paper was to find the optimal conditions for extracting high amounts of bioactive compounds from R. typhina fruits using ultrasound-assisted and [...] Read more.

Rhus typhina, an invasive plant species, contains valuable compounds that can be utilized in various fields. The main aim of this paper was to find the optimal conditions for extracting high amounts of bioactive compounds from R. typhina fruits using ultrasound-assisted and bead-beating techniques under different parameters (solvent concentration, solvent/solid ratio, extraction time, bead size, and material). A Box–Behnken design was applied for ultrasound-assisted extraction. The following process parameters were found to be optimal: 20/1 solvent/solid ratio (v/w), 61.51% aqueous ethanol, 10 min extraction time, with a composite desirability of 0.7719. The HPLC profile indicates that p-coumaric acid was the most abundant phenolic compound found in the BBE extract. The BBE extract was subjected to in vitro biological tests. The results indicate a high antimicrobial activity on Streptococcus pyogenes (20 mm inhibition zone) and Salmonella enterica (12 mm inhibition zone). A hemolysis rate of 19.85% was found at an extract concentration of 1000 µg/mL on sheep erythrocytes. We report for the first time the protective role of the extract on cell viability of human gingival fibroblasts, but also a weak antiproliferative effect on the HepG2 human liver cancer cell line. Overall, we conclude that R. typhina fruits are rich in bioactive compounds that can be recovered using proper extraction conditions. Further research is required to understand and valorize their biological potential. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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18 pages, 1212 KiB

Open AccessArticle

Synthesis, Structure, and In Vitro Biological Evaluation of Semi-Synthetic Derivatives of Betulin

by Elwira Chrobak, Marta Świtalska, Joanna Wietrzyk and Ewa Bębenek

Appl. Sci. 2024, 14(21), 9970; https://doi.org/10.3390/app14219970 - 31 Oct 2024

Cited by 1 | Viewed by 1010

Abstract

Betulin and α-lipoic acid are naturally occurring substances with different biological properties. Combining two phytochemical units into a conjugate is a frequently used method to obtain new compounds with better pharmacokinetic parameters. This research concerned the preparation of lipoate derivatives of betulin using [...] Read more.

Betulin and α-lipoic acid are naturally occurring substances with different biological properties. Combining two phytochemical units into a conjugate is a frequently used method to obtain new compounds with better pharmacokinetic parameters. This research concerned the preparation of lipoate derivatives of betulin using the Steglich method. Experimental lipophilicity values were determined for target compounds 6–10 by reversed-phase thin-layer chromatography. In silico methods were used to calculate the physicochemical parameters and lipophilicity of new derivatives and to determine the probable directions of biological activity. α-Lipoic acid, betulin, and lipoate derivatives 6–10 were tested for antiproliferative activity against MV4-11, A549, MCF-7, PC-3, HCT116, MiaPaca-2, and Hs294T cancer cells. 3-(5-(1,2-Dithiolan-3-yl)pentanoyl))betulin 10 showed moderate anticancer activity against MV4-11, PC-3, and HCT116, with IC₅₀ values in the range of 39.8–76.7 µM. The introduction of a dithiolate substituent at the C3 position in 28-acetylbetulin gave compound 9 the highest activity (IC₅₀ = 37.9 µM), in the ratio of biphenotypic B myelomonocytic leukemia cells (MV4-11). All lipoate derivatives were inactive towards normal cells. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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15 pages, 6094 KiB

Open AccessArticle

Glycine-Conjugated α-Mangostins as Potential Estrogen Receptor Alpha (ERα) Antagonists through Pharmacophore Modeling, Docking Analysis, and Molecular Dynamics Simulations

by Hanggara Arifian, Rani Maharani, Sandra Megantara, Nur Kusaira Khairul Ikram and Muchtaridi Muchtaridi

Appl. Sci. 2024, 14(13), 5549; https://doi.org/10.3390/app14135549 - 26 Jun 2024

Cited by 2 | Viewed by 1725

Abstract

Natural compounds have demonstrated good biological activity when combined with certain amino acids. For example, a glycine-conjugated glycyrrhetinic acid exhibits heightened efficiency against MCF7 cancer cells. Consequently, a molecular modeling analysis is conducted to construct glycine-conjugated α-mangostins and investigate their potential. According to [...] Read more.

Natural compounds have demonstrated good biological activity when combined with certain amino acids. For example, a glycine-conjugated glycyrrhetinic acid exhibits heightened efficiency against MCF7 cancer cells. Consequently, a molecular modeling analysis is conducted to construct glycine-conjugated α-mangostins and investigate their potential. According to pharmacophore modeling using the ligand-based drug design technique, only two glycine-conjugated α-mangostins conform to the pharmacophore features. The docking simulation results show that the Am1Gly conjugate can interact with the estrogen receptor-α (ERα) with a binding energy of −10.91 kcal/mol. This interaction is further supported by molecular dynamics simulations performed over a 200 ns timeframe. Based on molecular dynamics modeling using the MMPBSA method, the binding affinity of Am1Gly (ΔG_Total = −48.79 kcal/mol) is determined. The results of this analysis indicate that Am1Gly might function as an antagonist to estrogen receptors. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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10 pages, 4134 KiB

Open AccessArticle

Identifying p56^lck SH2 Domain Inhibitors Using Molecular Docking and In Silico Scaffold Hopping

by Priyanka Samanta and Robert J. Doerksen

Appl. Sci. 2024, 14(10), 4277; https://doi.org/10.3390/app14104277 - 17 May 2024

Cited by 2 | Viewed by 1807

Abstract

Bacterial infections are the second-leading cause of death, globally. The prevalence of antibacterial resistance has kept the demand strong for the development of new and potent drug candidates. It has been demonstrated that Src protein tyrosine kinases (TKs) play an important role in [...] Read more.

Bacterial infections are the second-leading cause of death, globally. The prevalence of antibacterial resistance has kept the demand strong for the development of new and potent drug candidates. It has been demonstrated that Src protein tyrosine kinases (TKs) play an important role in the regulation of inflammatory responses to tissue injury, which can trigger the onset of several severe diseases. We carried out a search for novel Src protein TK inhibitors, commencing from reported highly potent anti-bacterial compounds obtained using the Mannich reaction, using a combination of e-pharmacophore modeling, virtual screening, ensemble docking, and core hopping. The top-scoring compounds from ligand-based virtual screening were modified using protein structure-based design approaches, and their binding to the Src homology-2 domain of p56^lck TK was predicted using ensemble molecular docking. We have prepared a database of 202 small molecules and have identified six novel top hits that can be subjected to further investigation. We have also performed in silico ADMET property prediction for the hit compounds. This combined computer-aided drug design approach can serve as a starting point for identifying novel TK inhibitors that could be further subjected to in vitro studies and validation of antimicrobial activity. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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14 pages, 4345 KiB

Open AccessArticle

Thermal Analysis in the Evaluation of Solid Lipid Microparticles in the Form of Aqueous Dispersion and Fine Powder

by Eliza Wolska and Géza Regdon, Jr.

Appl. Sci. 2023, 13(24), 13282; https://doi.org/10.3390/app132413282 - 15 Dec 2023

Cited by 5 | Viewed by 1337

Abstract

In the presented study, an attempt was made to investigate the most important attributes of solid lipid microparticles (SLM) using thermal analysis (DSC/TG) in order to determine the importance of this technique in the research and development of lipid microparticles. Particularly interesting in [...] Read more.

In the presented study, an attempt was made to investigate the most important attributes of solid lipid microparticles (SLM) using thermal analysis (DSC/TG) in order to determine the importance of this technique in the research and development of lipid microparticles. Particularly interesting in our studies were drug–lipid interactions and modifications of the SLM matrix structure induced by the production method (the hot emulsification method) and further processing (e.g., spray drying), as well as changes occurring during the stability studies. Cyclosporine A, indomethacin and spironolactone were used as model active substances incorporated into SLM. The conducted research demonstrated the significant potential of DSC/TG, especially for the analysis of SLM in the form of fine powder. The method of sample preparation, consisting of evaporation of water at room temperature, turned out to be crucial for the DSC/TG analysis of SLM dispersion. In the case of the tested SLM, the basic and usually the only observed thermal transformation in the DSC spectrum was the endothermic peak associated with the lipid forming a microsphere matrix. This peak is the main source of information about the properties and stability of the tested SLM. The obtained results show that glyceryl behenate (Compritol) is a significantly better lipid for forming lipid microparticles than stearic acid. Although thermal transformations of the incorporated drug substances are not directly visible in the DSC spectra, their impact on the SLM properties can be assessed indirectly, based on changes in the lipid melting point and the shape of the DSC and TG peaks and curves. DSC/TG studies confirmed the lack of an effect of the spray drying process on the properties of drug-loaded SLM with Compritol. Studies have also shown up to a 2-year stability of SLM with CsA. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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Review

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40 pages, 11080 KiB

Open AccessReview

Terpenes as Potential Anti-Alzheimer’s Disease Agents

by Elisabete Lima and Jorge Medeiros

Appl. Sci. 2024, 14(9), 3898; https://doi.org/10.3390/app14093898 - 2 May 2024

Cited by 10 | Viewed by 2462

Abstract

Alzheimer’s disease (AD), a slowly progressive neurodegenerative disorder, is the main cause of dementia worldwide. However, currently, the approved drugs to combat AD are effective only in treating its symptoms. In fact, an efficacious treatment for this complex and multifactorial disorder remains to [...] Read more.

Alzheimer’s disease (AD), a slowly progressive neurodegenerative disorder, is the main cause of dementia worldwide. However, currently, the approved drugs to combat AD are effective only in treating its symptoms. In fact, an efficacious treatment for this complex and multifactorial disorder remains to be discovered, demanding the urgent development of new therapeutic approaches for the disease, such as the use of bioactive secondary metabolites (SMs) from natural sources. Sessile organisms, like plants, are unable to escape from adverse environmental conditions and must therefore create their own defense. Their main defense strategy is chemical defense that includes the production of an enormously diverse array of bioactive SMs, such as terpenes and their derivatives. This largest and most diverse group of plant SMs also provide the treatment of several diseases due to their broad-spectrum bioactivities, for example, anticancer, antioxidant, and anti-inflammatory properties. Thus, the evaluation of the neuroprotective potential of terpenes is imperative. It is known that the major AD clinical indications (CIs) are extracellular senile plaques of amyloid-β (Aβ) protein, intracellular hyperphosphorylated tau (τ) neurofibrillary tangles (NFTs), uncommon neuroinflammatory response, oxidative stress, and synaptic and neuronal dysfunction. Therefore, terpenes that may decrease these CIs might be used for AD treatment. Surely, terpenes targeting more than one AD pathogenic mechanism, multi-target drug ligands (MTDLs), have the potential to become a leading AD treatment. Thus, this review analyzes, for each CI, the scaffolds of the selected terpenes leading to the highest activity. Full article

(This article belongs to the Special Issue Research on Organic and Medicinal Chemistry)

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