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Herein, we report the obtaining of new hybrid molecules of amphetamine with different profens (amfens). The obtained amfens are characterized by their melting points, UV, 1H–, 13C–NMR, and HRMS spectra. A complete and detailed mass spectral analysis of the newly obtained derivatives of amphetamine with ibuprofen, flurbiprofen, ketoprofen, naproxen, and carprofen was performed. In vitro inhibition of albumin denaturation of each new compound was assessed, and they showed significant activity. The IC50 values of the obtained amphetamine-profen derivatives ranged from 92.81 to 159.87 µg/mL. This indicates that the new hybrids inherit the anti-inflammatory properties of profens. Using in silico method, the toxicity was also calculated. The obtained results are given in LD50 values. Depending on the route of administration, the amfens are less toxic compared to the standard amphetamine.

Herein we report the synthesis of (±)-N-(3-chlorophenethyl)-2-(6-methoxynaphthalen-2-yl)propanamide in the reaction between 2-(3-chlorophenyl)ethan-1-amine and (±)-naproxen. The newly obtained bio-functional hybrid molecule was fully characterized via 1H, 13C NMR, UV, IR, and mass spectral data.

Herein we report an alternative eco-friendly method for the synthesis of 1,2,3,4-tetrahydroisoquinoline sulfonamide derivatives. All obtained compounds were screened for their in vitro inhibition of albumin denaturation, antioxidant, antitryptic and antibacterial activity, and have shown significant results. The lipophilicity was established using both reversed-phase thin layer chromatography and in silico calculations.

N-(3-chlorophenethyl)-2-(4-isobutylphenyl)propanamide was synthesized for the first time in the reaction between 2-(3-chlorophenyl)ethan-1-amine and 2-(4-isobutylphenyl)propanoyl chloride with high yield. The newly obtained chlorine-containing ibuprofen derivative was fully analyzed and characterized using 1H-, 13C-NMR, UV, and mass spectral data.

Herein, we report the synthesis of new hybrid molecules between furan and N-containing heterocyclic compounds such as pyrrolidine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline, and piperidine. The obtained compounds were fully characterized using 1H- and 13C-NMR, UV-Vis, and HRMS spectra. All compounds were assessed for their anti-inflammatory, anti-arthritic, antioxidant, reducing power ability, and chelating activity. The less lipophilic molecules H2 (60.1 ± 8.16) and H4 (62.23 ± 0.83) had almost 12 times higher ATA compared with the used ketoprofen (720.57 ± 19.78) standard. The inhibition of albumin denaturation results makes the newly obtained hybrids potential anti-inflammatory drugs, as the expressed values are higher than the ketoprofen standard (126.58 ± 5.00), except H3 (150.99 ± 1.16). All four compounds show significant activity regarding the in vitro biological activities, which makes them great candidates for potential future drugs.

Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation activity. The lipophilicity was established using both reversed-phase thin layer chromatography and in silico calculations.

2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide was synthesized by a reaction between amphetamine and flurbiprofen in high yields. The newly obtained hybrid molecule was fully analyzed and characterized via 1H, 13C, UV, IR, HPLC, and mass spectral data.

N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between benzo[d]thiazol-2-amine and flurbiprofen in high yield. The newly obtained flurbiprofen derivative was fully analyzed and characterized via 1H, 13C, UV, IR, and mass spectral data.

Due to their beneficial medicinal effects, in recent years there has been an increasing interest in the research of flavonoids in plant sources. In the conducted research the flavonoid composition of Chenopodium botrys was defined by applying an approach which included different extraction procedures and methods of detection. Primary extraction of polyphenols with two different solvents, HPLC-PDA fingerprint profiling and an Orbitrap UHPLC-MS/MS detection were used. The fingerprint profile of polyphenols showed that the major constituents were the methoxylated flavones nepetin, hispidulin and jaceosidin, while the quercetin glycosides represented a minor part. In order to elucidate their structure, the fragmentation of the compounds was examined by means of ESI-MS/MS analysis. A novel explanation of the fragmentation pathways of the methoxylated flavones was introduced. Nepetin, nobiletin, eupatilin, rutin and quercetin-3-O-galactoside were identified in the polyphenol complex of C. botrys for the first time.

The title compound was obtained in high yield in the reaction between tryptamine and naproxen. The newly synthesized naproxen derivative was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data.

This study investigates the relationships between the main polyphenols and DPPH radical scavenging activity (RSA) in extracts from some of the most common wild and cultivated species from the Achillea millefolium group, Mentha, Chenopodium botrys, Clinopodium vulgare and Artemisia vulgaris. Another aspect of the study is the effects of choosing an extraction solvent, highlighting the importance of selecting an appropriate one for obtaining extracts with maximum manifested bioactivity. Chemical characterization of compounds is performed. It is based on HPLC-PDA fingerprint profiles, obtained from 70% aqueous methanol extracts. Hydroxycinnamic acids, glycosides of luteolin (LG), apigenin (AG), their aglycones and methoxyflavones are found to be the most abundant components, which have the highest impact on radical scavenging activity (RSA) of the extracts. The data allow supposing high correlation relationships between caffeoylquinic acids and RSA of extracts from four A. millefolium group species and cv. Proa. Cl. vulgare methanol extract, rich in rosmarinic acid, LG and AG, showed the highest RSA with IC50 10.37μg.mL-1. In contrast, extracts of Ch. botrys which lack phenolic acids, contain low amount of glycosides and are rich in methoxyflavone aglycones, possess very weak RSA. For multicomponent analysis, our data suggest 70% methanol as the most appropriate solvent for extraction of compounds belonging to the polyphenol complex. Based on the high quantities of rosmarinic acid, luteolin and apigenin glycosides, 66% ethanol solvent is found to be the best choice for medicinal consumption extracts.

Maintaining a strong antioxidant system is essential for preventing drought-induced oxidative stress. Thus, in the present study we investigated the role of some non-enzymic and enzymic antioxidants in desiccation tolerance of Haberlea rhodopensis. The effects of high light upon desiccation on antioxidant capacity was estimated by comparing the response of shade and sun plants. The significant enhancement of the antioxidant capacity at 8% RWC corresponded to an enormous increase in flavonoid content. The important role of ascorbate-glutathione cycle in overcoming oxidative stress during drying of H. rhodopensis was established. The antioxidant capacity increased upon dehydration of both shade and sun plants but some differences in non-enzymatic and enzymatic antioxidants were observed. Investigations on the role of polyphenols in desiccation tolerance are scarce. In the present study the polyphenol profiles (fingerprints) of the resurrection plant Haberlea rhodopensis, including all components of the complex are obtained for the first time. It was clarified that the polyphenol complex of H. rhodopensis includes only two types of glycosides - phenylethanoid glucosides and hispidulin 8-C-glucosides. Upon desiccation the polyphenol content increase and the main role of phenylethanoid glucosides in the protection of H. rhodopensis was revealed.

This paper describes an analytical approach for polyphenol components determination in Vernonia amygdalina Del. (VA) using surrogate standards, extracts of green coffee and Achillea asplenifolia 9602, and rutin as an internal standard. HPLC–PDA fingerprint profiles of the polyphenol complex of VA and surrogate standards were developed. By comparison between the chromatographic and spectral characteristics of VA and the surrogate standards using the relative retention times towards rutin, it was possible to identify the polyphenol components in VA. Additionally, peak identity was confirmed by HRMS spectra, to verify the truthfulness of the procedures. Recoveries of rutin, LOD, LOQ, and RSD% were determined, to validate the method as highly accurate and applicable. The polyphenol complex of VA contained dicaffeoylquinic acids and luteolin glycosides as main components. A method using Nucleosil C18 provided the best separation of 1,5- and 3,5-dicaffeoylquinic acids in VA. Their amount reached up to 1.49 ± 0.21 mg g −1 . The content of 4,5-dicaffeoylquinic acid was 0.35 ± 0.04 mg g −1 . Luteolin glycosides and luteolin were found at 0.40 ± 0.04 mg g −1 and 0.14 ± 0.01 mg g −1 , respectively. The presence of luteolin 4′- O -glucoside, apigenin 7- O -rutinoside, apigenin 7- O -glucoside and apigenin as minor constituents in VA is reported for the first time. Results suggest the implementation of the surrogate standard approach in food analytical practice as highly advisable.

The chemical composition and the antimicrobial and antioxidant activity of essential oils from two Helichrysum italicum (Roth) G.Don subspecies grown in Bulgaria were investigated. As a result, 95 compounds with concentrations above 0.05% were detected by GC/MS and 46 of them, mainly mono- and sesquiterpenes, representing 79.81% and 85.51% of the total content of the samples, were identified. The main constituents of the essential oil from Helichrysum italicum subsp. microphyllum (plant origin from Bosnia) were monoterpene alpha-pinene (20.84%) and sesquiterpene gamma-curcumene (16.53%), followed by beta-selinene (5.59%), ar-curcumene (4.39%), trans-caryophyllene (4.35%), beta-diketone italidione I (4.32%), alpha-selinene (4.28%), and neryl acetate (3.81%). The sesquiterpene hydrocarbons were the dominant groups of chemical constituents in the essential oil, followed by the oxygenated aliphatic hydrocarbons. The main constituents in the H. italicum essential oil (plant origin from France) were neryl acetate (33.87%), gamma-curcumene (8.84%), rosifoliol (5.46%), geranyl propionate (4.98%), alpha r-curcumene (4.31%), italidione I (3.56%), alpha-eudesmol (3.19%), and limonene (3.02%). The main class of chemical compounds was the oxygenated monoterpenes, followed by sesquiterpene hydrocarbons. H. italicum essential oil from France showed more pronounced antimicrobial activity against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, and the fungus Aspergillus brasiliensis, as well as stronger antioxidant potential.