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21 pages, 4187 KiB  
Article
Preparation and Application of a Novel Liquid Oxygen-Compatible Epoxy Resin of Fluorinated Glycidyl Amine with Low Viscosity
by Jianing Wei, Jia Yan, Shichao Li, Juanzi Li and Zhanjun Wu
Polymers 2024, 16(19), 2759; https://doi.org/10.3390/polym16192759 (registering DOI) - 29 Sep 2024
Abstract
A liquid oxygen-compatible epoxy resin of fluorinated glycidyl amine (TFEPA) with a low viscosity of 260 mPa·s in a wide range of temperatures, from room temperature to 150 °C, was synthesized and used to decrease the viscosity of phosphorus-containing bisphenol F epoxy resins. [...] Read more.
A liquid oxygen-compatible epoxy resin of fluorinated glycidyl amine (TFEPA) with a low viscosity of 260 mPa·s in a wide range of temperatures, from room temperature to 150 °C, was synthesized and used to decrease the viscosity of phosphorus-containing bisphenol F epoxy resins. And the forming process and application performances of this resin system and its composite were investigated. The viscosity of the bisphenol F resin was decreased from 4925 to 749 mPa·s at 45 °C by mixing with 10 wt.% TFEPA, which was enough for the filament winding process. Moreover, the processing temperature and time windows were increased by 73% and 186%, respectively. After crosslinking, the liquid oxygen compatibility was preserved, and its tensile strength, elastic modulus, and breaking elongation at −196 °C were 133.31 MPa, 6.59 GPa, and 2.36%, respectively, which were similar to those without TFEPA. And the flexural strength and modulus were 276.14 MPa and 7.29 GPa, respectively, increasing by 21.73% in strain energy at flexural breaking, indicating an enhanced toughness derived from TFEPA. Based on this resin system, the flexural strength and toughness of its composite at −196 °C were 862.73 MPa and 6.88 MJ/m3, respectively, increasing by 4.46% and 10.79%, respectively. Full article
(This article belongs to the Section Polymer Applications)
21 pages, 8570 KiB  
Article
Transcriptome and Metabolome Analyses Reveal the Molecular Mechanisms of Albizia odoratissima’s Response to Drought Stress
by Shuoxing Wei, Feng Gao, Zhihui Wang, Guoping Yin, Shizhi Wen, Hanbiao Ou and Zhiming Liu
Plants 2024, 13(19), 2732; https://doi.org/10.3390/plants13192732 (registering DOI) - 29 Sep 2024
Abstract
Albizia odoratissima is a deciduous tree species belonging to the family Leguminosae. It is widely distributed in the southern subtropical and tropical areas of China and has important ecological and economic value. The growth and metabolic processes of A. odoratissima are affected [...] Read more.
Albizia odoratissima is a deciduous tree species belonging to the family Leguminosae. It is widely distributed in the southern subtropical and tropical areas of China and has important ecological and economic value. The growth and metabolic processes of A. odoratissima are affected by drought stress, but the molecular mechanisms remain unknown. Therefore, this study investigated the physicochemical properties, gene expression, and metabolites of A. odoratissima seedlings under drought stress. The results show that, in leaves of A. odoratissima seedlings, drought stress reduced the moisture content, chlorophyll content, photosynthetic efficiency, superoxide dismutase (SOD) activity, and gibberellin (GA) and indoleacetic acid (IAA) contents while increasing the catalase (CAT) and peroxidase (POD) activities and malondialdehyde (MDA), proline, soluble sugar, and soluble protein contents. Within the CK5 (Day 5 of control group) vs. T5 (Day 5 of drought treatment), CK10 vs. T10, CK15 vs. T15, and CK20 vs. T20 groups (CK: control group; T: drought treatment), a total of 676 differentially expressed genes (DEGs) were upregulated and 518 DEGs were downregulated, and a total of 228 and 143 differential accumulation metabolites (DAMs) were identified in the CK10 vs. T10 and CK20 vs. T20 groups. These were mainly involved in the amino acid and alkaloid metabolism pathways in the leaves of the A. odoratissima seedlings. In the amino acid and alkaloid biosynthesis pathways, the relative expression levels of the AoproA (Aod04G002740, ORTHODONTIC APPLIANCE), AoOAT (Aod07G015970, ORNITHINE-OXO-ACID TRANSAMINASE), and AoAOC3 (Aod12G005010/08G003360/05G023920/08G003000/08G003010, AMINE OXIDASE COPPER CONTAINING 3) genes increased, which concurrently promoted the accumulation of arginine, proline, piperine, cadaverine, and lysine. Furthermore, some key transcription factors in the response to drought were identified in the leaves using the weighted gene co-expression network analyses (WGCNA) method. These findings reveal that A. odoratissima seedlings respond to drought stress by improving the capacities of the antioxidant system and secondary metabolism. Full article
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23 pages, 4228 KiB  
Article
Crystal Structure, Supramolecular Organization, Hirshfeld Analysis, Interaction Energy, and Spectroscopy of Two Tris(4-aminophenyl)amine-Based Derivatives
by Mayra M. Luna-Martínez, Marcos Morales-Santana, José Martín Santiago-Quintana, Efrén V. García-Báez, Jayanthi Narayanan, María de Jesús Rosales-Hoz and Itzia I. Padilla-Martínez
Crystals 2024, 14(10), 855; https://doi.org/10.3390/cryst14100855 (registering DOI) - 29 Sep 2024
Abstract
The use of tris(4-aminophenyl)amine (TAPA) as central to the synthesis of both polyimines and polyimides and covalent organic frameworks and inorganic cages, among others, has grown in the last few years. The resulting materials exhibit high performance in their area of application. In [...] Read more.
The use of tris(4-aminophenyl)amine (TAPA) as central to the synthesis of both polyimines and polyimides and covalent organic frameworks and inorganic cages, among others, has grown in the last few years. The resulting materials exhibit high performance in their area of application. In this contribution, the crystal structures of two TAPA derivatives, triethyl (nitrilotris(benzene-4,1-diyl))tricarbamate (1) and triethyl 2,2′,2”-((nitrilotris(benzene-4,1-diyl))tris(azanediyl))tris(2-oxoacetate) (2), are described. The molecular and supramolecular structures of both compounds were compared between them and with analogous compounds. The analyses of their vibrational and 13C-CPMAS NMR spectroscopies, as well as their thermal stability, were included and corelated with the crystal structure. Hirshfeld surface analysis on the crystal structures of both TAPA derivatives revealed the stabilization of the crystal network via the amide N—H∙∙∙O interactions of dispersive nature in the carbamate, whereas dispersive carbonyl–carbonyl interactions also played a competitive role in the supramolecular arrangement of the oxamate. Interaction energy DFT calculations performed at the B3LYP/6-311G(d,p) level allowed us to estimate the energy contributions and nature of several interactions in terms of the stability of both crystal lattices. Full article
(This article belongs to the Section Macromolecular Crystals)
18 pages, 4204 KiB  
Article
Chemically Degradable Vitrimers Based on Divanillin Imine Diepoxy Monomer and Aliphatic Diamines for Enhanced Carbon Fiber Composite Applications
by Tommaso Telatin, Silvia De la Flor, Xavier Montané and Àngels Serra
Polymers 2024, 16(19), 2754; https://doi.org/10.3390/polym16192754 (registering DOI) - 29 Sep 2024
Abstract
This study presents the development of a diglycidyl monomer containing two imine groups that can act as dynamic and reversible bonds. During the curing of the monomer with two different amine hardeners, we confirmed the formation of new imine groups due to the [...] Read more.
This study presents the development of a diglycidyl monomer containing two imine groups that can act as dynamic and reversible bonds. During the curing of the monomer with two different amine hardeners, we confirmed the formation of new imine groups due to the transamination reaction between the imine groups of the diepoxy monomer with the amine groups of the hardener. The effect of this structural change was observed in the stress relaxation behavior, resulting in the overlapping of two different relaxation modes. The analytical modelling was able to extract two distinct characteristic relaxation times using a double-element Maxwell model. A second characterization of the stress relaxation process by frequency sweep experiments was performed to corroborate the results obtained, confirming speedy stress relaxation. Acid-catalyzed hydrolysis was performed on the studied materials, demonstrating the complete degradation of the network. We finally confirmed that the synthesized diepoxy compound is suitable for preparing carbon-fiber-reinforced composite materials, demonstrating easy fiber impregnation, fast reshaping, and especially a total degradation of the polymer matrix that allows for the recovery of the carbon fibers in mild conditions. This epoxy–amine system is an excellent candidate for overcoming the traditional limits of thermosets in preparing fiber-reinforced composites. Full article
(This article belongs to the Special Issue Epoxy Thermoset Polymer Composites)
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18 pages, 8986 KiB  
Article
Metagenomic and Metabolomic Profiling Reveals the Differences of Flavor Quality between Hongqu Rice Wines Fermented with Gutian Qu and Wuyi Qu
by Zihua Liang, Shiyun Chen, Hao Wang, Qi Wu, Weiling Guo, Li Ni and Xucong Lv
Foods 2024, 13(19), 3114; https://doi.org/10.3390/foods13193114 (registering DOI) - 29 Sep 2024
Abstract
Jiuqu (starter) makes an important contribution to the formation of the flavor characteristics of Hongqu rice wine (HQW). Gutian Qu (GTQ) and Wuyi Qu (WYQ) are two kinds of Jiuqu commonly used in HQW brewing, but the comparison of the two kinds of [...] Read more.
Jiuqu (starter) makes an important contribution to the formation of the flavor characteristics of Hongqu rice wine (HQW). Gutian Qu (GTQ) and Wuyi Qu (WYQ) are two kinds of Jiuqu commonly used in HQW brewing, but the comparison of the two kinds of HQW is still insufficient at present. The objective of this study was to compare the dynamic changes of amino acids (AAs), higher alcohols (HAs), bioamines (BAs), volatile flavor compounds (VFCs), and microbial communities in HQW fermentation, with GTQ and WYQ as starter. This study used an automatic amino acid analyzer, GC, HPLC, and GC-MS to detect AAs, HAs, Bas, and VFCs during fermentation; metagenomic sequencing technology was used to elucidate the microbial community and its functional characteristics. The results showed that the contents of AAs and HAs in HQW brewed with WYQ (WYW) were significantly higher than those in HQW brewed with GTQ (GTW). On the contrary, the majority of BAs in GTW were significantly higher than those in WYW. The composition of VFCs in WYW and GTW were obviously different, as most of the VFCs were notably enriched in WYW, while ethyl caproate, isoamyl acetate, ethyl heptanoate, ethyl nonanoate, 1-decanol, citronellol, phenethyl acetate, and hexanoic acid were more abundant in GTW. Burkholderia gladioli, Pantoea dispersa, Weissella cibaria, Monascus purpureus, and Saccharomyces cerevisiae were the predominant microbial populations in GTW brewing at the species level, while Sphingomonas sp., Kosakonia cowanii, Enterobacter asburiae, Leuconostoc lactis, Aspergillus niger, and Saccharomyces cerevisiae were the dominant microbial species in WYW brewing. The abundance of functional genes involved in BAs biosynthesis were much higher in GTW brewing, while the abundance of functional genes related to the metabolism of characteristic VFCs were much higher in WYW brewing. Collectively, these findings provided evidence for elucidating the effects of Jiuqu and microbial communities on HQW flavor quality, and laid a solid foundation for the improvement of HQW flavor quality. Full article
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28 pages, 1833 KiB  
Review
Comparative Review for Enhancing CO2 Capture Efficiency with Mixed Amine Systems and Catalysts
by Wenhao Jiang, Yuchen Lin, Chengqi Sun, Yin Sun and Yunlong Zhu
Molecules 2024, 29(19), 4618; https://doi.org/10.3390/molecules29194618 (registering DOI) - 29 Sep 2024
Abstract
This study investigates methods to enhance the efficiency of CO2 capture using organic amine absorption and compares the performance of traditional and novel amine solvents. It reviews various single-component and mixed amine absorbents, as well as catalysts used in these methods, highlighting [...] Read more.
This study investigates methods to enhance the efficiency of CO2 capture using organic amine absorption and compares the performance of traditional and novel amine solvents. It reviews various single-component and mixed amine absorbents, as well as catalysts used in these methods, highlighting the superiority of mixed amine absorbents over single-component amine absorbents in CO2 absorption and desorption. Additionally, the study explores the catalytic mechanisms and effects of catalysts in the CO2 absorption/desorption process with amine solvents and provides an outlook on future research directions. The aim is to promote the widespread adoption of organic amine absorption technology in industrial applications and to contribute to the development of more sustainable and efficient CO2 capture technologies. Full article
17 pages, 1454 KiB  
Article
Techno-Economic Assessment of Amine-Based Carbon Capture in Waste-to-Energy Incineration Plant Retrofit
by Michele Bertone, Luca Stabile, Gino Cortellessa, Fausto Arpino and Giorgio Buonanno
Sustainability 2024, 16(19), 8468; https://doi.org/10.3390/su16198468 (registering DOI) - 29 Sep 2024
Abstract
This study offers a detailed techno-economic assessment of Carbon Capture (CC) integration in an existing Waste-to-Energy (WtE) incineration plant, focusing on retrofit application. Post-combustion carbon capture using monoethanolamine (MEA) was modeled for various low-scale plant sizes (3000, 6000, and 12,000 t of CO [...] Read more.
This study offers a detailed techno-economic assessment of Carbon Capture (CC) integration in an existing Waste-to-Energy (WtE) incineration plant, focusing on retrofit application. Post-combustion carbon capture using monoethanolamine (MEA) was modeled for various low-scale plant sizes (3000, 6000, and 12,000 t of CO2 per year), using a process simulator, highlighting the feasibility and implications of retrofitting a WtE incineration plant with CC technology. The comprehensive analysis covers the design of the CC plant and a detailed cost evaluation. Capture costs range from 156 EUR/t to 90 EUR/t of CO2. Additionally, integrating the CO2 capture system reduces the overall plant absolute efficiency from 22.7% (without carbon capture) to 22.4%, 22.1%, and 21.5% for the different capture capacities. This research fills a gap in studying small-scale CC applications for the WtE incineration plants, providing critical insights for similar retrofit projects. Full article
(This article belongs to the Topic CO2 Capture and Renewable Energy)
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9 pages, 1993 KiB  
Proceeding Paper
Synthesis of Hexamethylenetetramine Mono- and Di(P-Methoxyphenylacetochloride)
by Ruzimurod Jurayev Sattorovich, Azimjon Choriev Uralivich and Bekzod Eshqulov Ravshan ugli
Eng. Proc. 2024, 67(1), 53; https://doi.org/10.3390/engproc2024067053 - 26 Sep 2024
Abstract
In this study, hexamethylenetetramine mono- and di(p-methoxyphenylacetochloride) synthesis is presented in a clear and effective manner. Under mild conditions, p-methoxyphenylacetyl chloride and hexamethylenetetramine undergo a synthesis reaction. By adjusting the reactant and reaction conditions, the mono- and di-substituted products were produced selectively. The [...] Read more.
In this study, hexamethylenetetramine mono- and di(p-methoxyphenylacetochloride) synthesis is presented in a clear and effective manner. Under mild conditions, p-methoxyphenylacetyl chloride and hexamethylenetetramine undergo a synthesis reaction. By adjusting the reactant and reaction conditions, the mono- and di-substituted products were produced selectively. The reaction of 4-methoxyphenylchloroacetate with various amines is a nucleophilic exchange reaction, and it was found that these reactions can proceed under normal conditions at the liquefaction temperature of the solvent. Before carrying out these reactions, the properties of amines were studied briefly. It can be found that the activity of the hydrogen attached to the nitrogen atom of amines depends on the nature of the group attached to the nitrogen. This relationship was expressed by Menshutkin’s kinetic equation and Arrinius’ equations. In addition, it became known that the reactions can be carried out easily due to the activity of the electrons that are not involved in the bond. To study the reactivity of tertiary amines, uratropin was chosen and its 4-methoxyphenylchloroacetate was reacted at 1:1 and 1:2 ratios, and the products were isolated. When the spectra of the obtained substances were analyzed, it was proven that a new substance was formed with the presence of an absorption region characteristic of the N-substituted amine group. Full article
(This article belongs to the Proceedings of The 3rd International Electronic Conference on Processes)
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17 pages, 5615 KiB  
Article
Sex-Specific Lipid Profiles and Flavor Volatiles in Giant Salamander (Andrias davidianus) Tails Revealed by Lipidomics and GC-IMS
by Shibo Zhao, Jinghong Yu, Linjie Xi, Xiangdong Kong, Jinjin Pei, Pengfei Jiang, Ruichang Gao and Wengang Jin
Foods 2024, 13(19), 3048; https://doi.org/10.3390/foods13193048 - 25 Sep 2024
Abstract
To elucidate the relationships between lipid components and odor traits, this study comparatively characterized the distinct lipid compositions and flavor volatiles in giant salamander tails of different sexes via mass-spectrometry-based lipidomics and GC-IMS. A total of 3145 fat metabolites were detected in male [...] Read more.
To elucidate the relationships between lipid components and odor traits, this study comparatively characterized the distinct lipid compositions and flavor volatiles in giant salamander tails of different sexes via mass-spectrometry-based lipidomics and GC-IMS. A total of 3145 fat metabolites were detected in male and female giant salamander tails, with the largest contributors being triglycerides (TGs, 840) and phosphatidylcholines (PCs, 383). Notably, the contents of PCs and TGs were greater in female tails than in male tails, and the levels of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) were also greater in the female group. Additionally, a total of 45 volatile components were detected, namely, 14 aldehydes, 14 alcohols, 9 ketones, 3 acids, 3 esters, 1 ether, and 1 amine. Alcohols (29.96% to 34.85%) and aldehydes (21.07% to 22.75%) were the predominant volatiles. Multivariate statistical analysis revealed 22 key differential fats and 26 differential odor substances as distinguishing labels between sexes. Correlation analysis revealed that the concentrations of triethylamine, dimethyl sulfide, ethanol-D, and 3-methyl butanal-D were significantly positively correlated with the concentrations of diglyceride (DG) (26:6e), cardiolipin (CL) (59:4), acylcarnitine (AcCa) (22:4), and triglyceride (TG) (52:10) (p < 0.01). Threefold cross-validation revealed that the prediction accuracies of these differential lipids and volatile compounds for sex recognition via the random forest model were 100%. These findings might not only provide insight into the effects of sexes on the lipid and volatile profiles of giant salamander tails but also provide clues for their gender recognition. Full article
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14 pages, 4626 KiB  
Article
Salophen-Type Schiff Bases Functionalized with Pyridinium Halide Units as Metal-Free Catalysts for Synthesis of Cyclic Carbonates from Carbon Dioxide and Terminal Epoxides
by Aleksandra Kawka, Karol Bester, Agnieszka Bukowska and Wiktor Bukowski
Catalysts 2024, 14(10), 658; https://doi.org/10.3390/catal14100658 - 24 Sep 2024
Abstract
Objectives: Salophen-type Schiff bases functionalized with 4-(dimethylamino)pyridinium halide units are shown to be effective single-component catalysts for the synthesis of cyclic carbonates from terminal epoxides and carbon dioxide. Methods: Using one of such trifunctional organocatalysts, epichlorohydrin could be selectively converted to the target [...] Read more.
Objectives: Salophen-type Schiff bases functionalized with 4-(dimethylamino)pyridinium halide units are shown to be effective single-component catalysts for the synthesis of cyclic carbonates from terminal epoxides and carbon dioxide. Methods: Using one of such trifunctional organocatalysts, epichlorohydrin could be selectively converted to the target cyclic carbonate under 2 bar of CO2 at 120 °C. Results: Over 80% conversion of E3 was then observed when organocatalyst S3 was used in the amount of 0.5 mol% (TON = 156) and even the use of 0.05 mol% S3 guaranteed almost 50% conversion of E3 to C3 (TON = 893). Conclusions: The presence of tertiary amine units in the molecules of these homogeneous organocatalysts proved to be crucial for the catalytic activity of developed organocatalysts. However, their catalytic activity was also supported by the presence of acidic phenolic units and halide ions as Lewis bases. Some closely related compounds were found to be clearly less active or inactive catalytically under the applied reaction conditions. Full article
(This article belongs to the Special Issue Advanced Catalysis for Energy and Environmental Applications)
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21 pages, 3338 KiB  
Article
Biochemical and Epigenetic Regulation of Glutamate Metabolism in Maize (Zea mays L.) Leaves under Salt Stress
by Alexander T. Eprintsev, Galina B. Anokhina, Polina S. Selivanova, Polina P. Moskvina and Abir U. Igamberdiev
Plants 2024, 13(18), 2651; https://doi.org/10.3390/plants13182651 - 21 Sep 2024
Abstract
The effect of salt stress (150 mM NaCl) on the expression of genes, methylation of their promoters, and enzymatic activity of glutamate dehydrogenase (GDH), glutamate decarboxylase (GAD), and the 2-oxoglutarate (2-OG)–dehydrogenase (2-OGDH) complex was studied in maize (Zea mays L.). GDH activity [...] Read more.
The effect of salt stress (150 mM NaCl) on the expression of genes, methylation of their promoters, and enzymatic activity of glutamate dehydrogenase (GDH), glutamate decarboxylase (GAD), and the 2-oxoglutarate (2-OG)–dehydrogenase (2-OGDH) complex was studied in maize (Zea mays L.). GDH activity increased continuously under salt stress, being 3-fold higher after 24 h. This was accompanied by the appearance of a second isoform with lower electrophoretic mobility. The expression of the Gdh1 gene strongly increased after 6–12 h of incubation, which corresponded to the demethylation of its promoter, while Gdh2 gene expression slightly increased after 2–6 h and then decreased. GAD activity gradually increased in the first 12 h, and then returned to the control level. This corresponded to the increase of Gad expression and its demethylation. Salt stress led to a 2-fold increase in the activity of 2-OGDH during the first 6 h of NaCl treatment, then the activity returned to the control level. Expression of the genes Ogdh1 and Ogdh3 peaked after 1–2 h of incubation. After 6–8 h with NaCl, the expression of these genes declined below the control levels, which correlated with the higher methylation of their promoters. We conclude that salt stress causes a redirection of the 2-OG flux to the γ-aminobutyric acid shunt via its amination to glutamate, by altering the expression of the Gdh1 and Gdh2 genes, which likely promotes the assembly of the native GDH molecule having a different subunit composition and greater affinity for 2-OG. Full article
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23 pages, 2386 KiB  
Article
Sustainable Biomethanol and Biomethane Production via Anaerobic Digestion, Oxy-Fuel Gas Turbine and Amine Scrubbing CO2 Capture
by Towhid Gholizadeh, Hamed Ghiasirad and Anna Skorek-Osikowska
Energies 2024, 17(18), 4703; https://doi.org/10.3390/en17184703 - 21 Sep 2024
Abstract
Energy policies around the world are increasingly highlighting the importance of hydrogen in the evolving energy landscape. In this regard, the use of hydrogen to produce biomethanol not only plays an essential role in the chemical industry but also holds great promise as [...] Read more.
Energy policies around the world are increasingly highlighting the importance of hydrogen in the evolving energy landscape. In this regard, the use of hydrogen to produce biomethanol not only plays an essential role in the chemical industry but also holds great promise as an alternative fuel for global shipping. This study evaluates a system for generating biomethanol and biomethane based on anaerobic digestion, biogas upgrading, methanol synthesis unit, and high-temperature electrolysis. Thermal integration is implemented to enhance efficiency by linking the oxy-fuel gas turbine unit. The integrated system performance is evaluated through thermodynamic modeling, and Aspen Plus V12.1 is employed for the analysis. Our findings show that the primary power consumers are the Solid Oxide Electrolysis Cell (SOEC) and Methanol Synthesis Unit (MSU), with the SOEC system consuming 824 kW of power and the MSU consuming 129.5 kW of power, corresponding to a production scale of 23.2 kg/h of hydrogen and 269.54 kg/h of biomethanol, respectively. The overall energy efficiency is calculated at 58.09%, considering a production output of 188 kg/h of biomethane and 269 kg/h of biomethanol. The amount of carbon dioxide emitted per biofuel production is equal to 0.017, and the proposed system can be considered a low-carbon emission system. Key findings include significant enhancements in biomethanol capacity and energy efficiency with higher temperatures in the methanol reactor. Full article
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16 pages, 5211 KiB  
Article
A Facile Route to Flavone-3-Carboxamides and Flavone-3-Carboxylates via Palladium-Catalyzed Amino- and Aryloxy-Carbonylation Reactions
by Sami Chniti, László Kollár, Attila Bényei, Ágnes Dörnyei and Attila Takács
Int. J. Mol. Sci. 2024, 25(18), 10128; https://doi.org/10.3390/ijms251810128 - 20 Sep 2024
Abstract
A library of C-3 functionalized flavones was successfully provided via palladium-catalyzed amino- and aryloxycarbonylation reactions of 3-iodoflavone (1), under mild conditions. This methodology showed good functional group tolerance using a variety of amines and phenols, under an atmospheric pressure of carbon [...] Read more.
A library of C-3 functionalized flavones was successfully provided via palladium-catalyzed amino- and aryloxycarbonylation reactions of 3-iodoflavone (1), under mild conditions. This methodology showed good functional group tolerance using a variety of amines and phenols, under an atmospheric pressure of carbon monoxide as a carbonyl source. While the flavone-3-carboxamides (2a-t) were produced in 22–79%, the flavone-3-carboxylates (4a′-l′) were obtained in excellent yields (up to 88%), under identical reaction conditions, just by switching N-nucleophiles to O-nucleophiles. The convenient availability of the involved starting materials confers simplicity to this approach to design new C-3-substituted flavones of biological relevance. The solid-state structures of flavone-3-carboxamide (2r) and flavone-3-ester (4f′) were further studied by single-crystal XRD analysis. Full article
(This article belongs to the Section Physical Chemistry and Chemical Physics)
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33 pages, 1551 KiB  
Review
Bioactive Compounds Produced by Endophytic Bacteria and Their Plant Hosts—An Insight into the World of Chosen Herbaceous Ruderal Plants in Central Europe
by Piotr Drożdżyński, Natalia Rutkowska, Magdalena Rodziewicz and Olga Marchut-Mikołajczyk
Molecules 2024, 29(18), 4456; https://doi.org/10.3390/molecules29184456 - 19 Sep 2024
Abstract
The natural environment has been significantly impacted by human activity, urbanization, and industrialization, leading to changes in living organisms and their adaptation to harsh conditions. Species, including plants, adapt to these changes by creating mechanisms and modifications that allow them to survive in [...] Read more.
The natural environment has been significantly impacted by human activity, urbanization, and industrialization, leading to changes in living organisms and their adaptation to harsh conditions. Species, including plants, adapt to these changes by creating mechanisms and modifications that allow them to survive in harsh environments. Also, endophytes, microorganisms that live inside plants, can support plant growth and defense mechanisms in these conditions by synthesizing antimicrobial secondary metabolites. What is more, endophytes produce bioactive metabolites, including alkaloids, amines, and peptides, which play a crucial role in the relationship between endophytes and their host organisms. Endophytes themselves benefit from this by creating a stable environment for their survival and development. The aim of this review is to gain insight into endophytic bioactive metabolites from chosen synanthropic ruderal plants. Industrial activities release pollutants like heavy metals, by-products, and waste, which challenge living organisms and require adaptation. Synanthropic plants, where endophytes are abundant, are particularly valuable for their bioactive compounds, which are used in agriculture and medicine. This review presents, among others, endophytes of herbaceous ruderal plants from central Europe—Chelidonium majus L., Urtica dioica L., Plantago lanceolata L., Matricaria chamomilla L., Equisetum arvense L., Oenothera biennis L., Silybum marianum L., and Mentha piperita L. Full article
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10 pages, 3901 KiB  
Communication
An Alternative Method for Synthesizing N,2,3-Trimethyl-2H-indazol-6-amine as a Key Component in the Preparation of Pazopanib
by Thi Thanh Cham Bui, Hue Linh Luu, Thi Thanh Luong, Thi Ngoc Nguyen, Nguyet Suong Huyen Dao, Van Giang Nguyen, Dinh Luyen Nguyen, Nguyen Trieu Trinh and Van Hai Nguyen
Chemistry 2024, 6(5), 1089-1098; https://doi.org/10.3390/chemistry6050063 - 19 Sep 2024
Abstract
Due to its application as an anti-cancer drug, pazopanib (1) has attracted the interest of many researchers, and several studies on pazopanib synthesis have been reported over the years. This paper provides a novel route for synthesizing N,2,3-trimethyl-2H-indazol-6-amine [...] Read more.
Due to its application as an anti-cancer drug, pazopanib (1) has attracted the interest of many researchers, and several studies on pazopanib synthesis have been reported over the years. This paper provides a novel route for synthesizing N,2,3-trimethyl-2H-indazol-6-amine (5), which is a crucial building block in the synthesis of pazopanib from 3-methyl-6-nitro-1H-indazole (6). By alternating between the reduction and two methylation steps, compound 5 was obtained in a yield comparable (55%) to what has been reported (54%). It is noteworthy that the last step of N2-methylation also yielded N,N,2,3-tetramethyl-2H-indazol-6-amine (5′) as a novel compound. Furthermore, the data presented in this paper can serve as a valuable resource for future research aimed at further refining the process of synthesizing pazopanib and its derivatives. Full article
(This article belongs to the Section Medicinal Chemistry)
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