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Anise hyssop (Agastache foeniculum (Pursh) Kuntze) is a perennial plant belonging to the Lamiaceae family mainly used in folk medicine to treat various ailments. This study determined the chemical composition of the essential oil and evaluated its antimicrobial and antioxidant activity. The essential oil was obtained from plants cultivated in the experimental field at the Institute of Roses, Essential and Medical Plants, Kazanlak, Bulgaria. The plants were processed by steam distillation, with the essential oil yielding 0.37%, and its main components being methyl chavicol (82.03%) and limonene (9.90%). The most potent antimicrobial action was observed against the gram-positive bacteria Staphylococcus aureus (25.7 mm inhibition zone) and Bacillus cereus (12.3 mm), the yeast Saccharomyces cerevisiae (16.3 mm) and Candida albicans (16.5 mm). The remaining gram-positive bacteria (Staphylococcus epidermidis and Bacillus subtilis), gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Salmonella ebony), and fungi (Aspergillus brasiliensis and Fusarium moniliforme) were resistant to the action of the essential oil. The antioxidant activity of the essential oil was ABTS (32.36 µmol TE/mL), DPPH (21.61 µmol TE/mL), CUPRAC (19.94 µmol TE/mL), and FRAP (29.56 µmol TE/mL) in vitro. Overall, the results from this study revealed the biological potential of anise hyssop as a source in pharmaceutical, food, and cosmetic applications.

Herein we report the synthesis of three novel sulfonamide derivatives of trimetazidine—medication primarily used to treat angina pectoris. The new compounds have been fully characterized with their melting point, 1H- and 13C-NMR, UV, and mass spectrometry. The collected data confirm the successful synthesis and structural integrity of the new molecules.

Herein, we report the synthesis of a series of new compounds by combining 2-aminobenzothiazole with various profens. The compounds were characterized using techniques such as 1H- and 13C-NMR, FT-IR spectrometry, and high-resolution mass spectrometry (HRMS), with detailed HRMS analysis conducted for each molecule. Their biological activities were tested in vitro, revealing significant anti-inflammatory and antioxidant effects, comparable to those of standard reference compounds. Lipophilicity was experimentally determined through partition coefficient (RM) measurements. To understand their binding affinity, molecular docking studies were perfsormed to analyze interactions with human serum albumin (HSA). The stability of these predicted complexes was further evaluated through molecular dynamics simulations. The results highlight the compounds’ promising biological activity and strong affinity for HSA. The new hybrid molecule between 2-ABT and ketoprofen 3b demonstrates significant promise based on the experimental data and is further supported by in silico calculations. Compound 3b exhibits the best hydrogen peroxide scavenging activity among the tested compounds, with an IC50 of 60.24 μg/mL. Furthermore, 3b also displays superior anti-inflammatory activity, with an IC50 of 54.64 μg/mL, making it more effective than the standard ibuprofen (76.05 μg/mL).

In this study, we report the synthesis of (±)-2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide through the reaction of 7-amino-4-methyl-2H-chromen-2-one with (±)-2-chloro-2-phenylacetyl chloride. The in vitro anti-inflammatory activity of the new compound was evaluated, and the results indicated that it exhibited superior activity compared to the standard, ibuprofen. The bio-functional hybrid compound underwent thorough detailed characterization utilizing 1H and 13C NMR, UV, and mass spectral analysis.

Herein, we report the synthesis of N-(3-chlorophenethyl)-4-nitrobenzamide in the reaction between 2-(3-chlorophenyl)ethan-1-amine and 4-nitrobenzoyl chloride. The newly obtained bio-functional hybrid molecule was fully characterized via 1H, 13C NMR, UV, and mass spectral data.

In this study, we outline the eco-friendly mechanosynthesis of N-(2,2-diphenylethyl)-4-nitrobenzamide by reacting 2,2-diphenylethan-1-amine with 4-nitrobenzoyl chloride. The resulting bio-functional hybrid compound was meticulously characterized through the analysis of 1H-, 13C-NMR, UV, and detailed mass spectral analysis.

Herein, we report the synthesis of 2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide in the reaction between 7-amino-4-methyl-2H-chromen-2-one and (±)-flurbiprofen. The newly-obtained bio-functional hybrid compound was fully characterized via 1H, 13C NMR, UV, and mass spectral data.

The title compound, (±)-N-(1,2-bis(3,4-dimethoxyphenyl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide, was obtained for the first time from 1,2-bis(3,4-dimethoxyphenyl) ethan-1-amine and (±)-flurbiprofen in one step. The newly synthesized bio-functional hybrid compound was fully characterized using 1H, 13C-NMR, UV, and mass spectral data.

In this study, we present the synthesis of five novel compounds by combining flurbiprofen with various substituted 2-phenethylamines. The synthesized derivatives underwent comprehensive characterization using techniques such as 1H- and 13C-NMR spectroscopy, UV-Vis spectroscopy, and high-resolution mass spectrometry (HRMS). Detailed HRMS analysis was performed for each of these newly created molecules. The biological activities of these compounds were assessed through in vitro experiments to evaluate their potential as anti-inflammatory and antioxidant agents. Furthermore, the lipophilicity of these derivatives was determined, both theoretically using the cLogP method and experimentally through partition coefficient (RM) measurements. To gain insights into their binding affinity, we conducted an in silico analysis of the compounds’ interactions with human serum albumin (HSA) using molecular docking studies. Our findings reveal that all of the newly synthesized compounds exhibit significant anti-inflammatory and antioxidant activities, with results statistically comparable to the reference compounds. Molecular docking studies further explain the observed in vitro results, shedding light on the molecular mechanisms behind their biological activities. Using in silico method, toxicity was calculated, resulting in LD50 values. Depending on the administration route, the novel flurbiprofen derivatives show lower toxicity compared to the standard flurbiprofen.

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.

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.

Helichrysum italicum has piqued the interest of many researchers in recent years, mostly for its essential oil, but increasingly for its polyphenolic content as well. In the current study, we examine the polyphenolic composition of H. italicum grown in Bulgaria. The polyphenolic complex was fractionated with solvents of various polarities, including hexane, chloroform, ethyl acetate, and butanol, in order to assess the biological impact of the components. HPLC-PDA and UHPLC-MS/MS were used to examine all fractions. The green coffee fingerprint profile was employed as a “surrogate standard” in the polyphenolic components detection approach. From the UHPLC-MS/MS analysis, we identified 60 components of the polyphenolic complex such as quercetin 3-O-glucuronide, quercetin acetyl-glycoside, isorhamnetin acetyl-glycoside, isorhamnetin caffeoyl-glycoside, quercetin caffeoyl-malonyl-glycoside, isorhamnetin coumaroyl-glycoside, coumaroyl-caffeoylquinic acid, and diCQA-acetyl-derivative were first reported in the composition of H. italicum. The biological activity of the fractions was evaluated in vitro and in silico, which included the fight against oxidative stress (hydrogen peroxide scavenging activity (HPSA), hydroxyl radical scavenging activity (HRSA), metal-chelating activity (MChA)) and nitrosative (nitric oxide scavenging activity) (NOSA)), in vitro anti-inflammatory, and anti-arthritic activity. Results are presented as IC50 ± SD μg/mL. The analysis showed that the EtOAc fraction was characterized by highest HPSA (57.12 ± 1.14 μg/mL), HRSA (92.23 ± 1.10 μg/mL), MChA (5.60 ± 0.17 μg/mL), and NOSA (89.81 ± 2.09 μg/mL), while the hexane and chloroform fractions showed significantly higher in vitro anti-inflammatory activity (30.48 ± 2.33 μg/mL, 62.50 ± 1.69 μg/mL) compared to the standard ibuprofen. All three fractions showed potential anti-arthritic activity (102.93 ± 8.62 μg/mL, 108.92 ± 4.42 μg/mL, 84.19 ± 3.89 μg/mL).

In the present work, we have investigated the polyphenolic composition of Chenopodium botrys from Bulgaria. The polyphenols were fractionated with solvents of varying polarity (n-hexane, chloroform, ethyl acetate, and n-butanol). The fractions were analyzed by HPLC-PDA and UHPLC-MS. The ethyl acetate fraction contained mono- and di-glycosides of quercetin, di-glycosides of kaempferol, and isorhamnetin and monoglycosides of hispidulin and jaceosidine. We found quercetin triglycosides in the butanol fraction. The ethyl acetate and butanol fractions contained 168.82 mg/g Extr and 67.21 mg/g Extr of quercetin glycosides, respectively. The main components of the polyphenolic complex in C. botrys were 6-methoxyflavones (355.47 mg/g Extr), which were found in the chloroform fraction. The flavonoids pectolinarigenin, demethylnobiletin, and isosinensetin, and the glycosides of quercetin (triglycosides, acylglycosides), kaempferol, isorhamnetin, hispidiulin, and jaceosidine, were discovered and reported in Chenopodium botrys for the first time. We used in vitro methods to assess the biological activity against oxidative stress (hydrogen peroxide scavenging activity (HPSA) and hydroxyl radical scavenging activity (HRSA)), nitrosative stress (nitric oxide scavenging activity (NOSA)), anti-inflammatory activity (IAD inhibition), and anti-tryptic activity (ATA). Quercetin mono- and di-glycosides exhibited greater HPSA and HRSA (IC50 = 39.18, 105.03 µg/mL), while 6-methoxyflavones had a greater NOSA (IC50 = 146.59 µg/mL). The same components showed the highest ATA (IC50 ranging from 116.23 to 202.44 µg/mL).

Three types of Lactuca sativa L. plants (green lettuces Batavia cv. Maritima and cv. Winter Butterhead, red lettuce Lolo rosa cv. Tuska) were investigated for their polyphenol composition. The lettuce plants were grown in polyethylene greenhouses and treated with different fertilisers. The qualitative and quantitative polyphenol composition was evaluated according to the use of mineral, organic (Italpollina and Arkobaleno) and bio (Lombricompost and EKOprop NX) fertilisers. The individual polyphenol components (caffeoyl derivatives and quercetin glycosides) were determined by high-performance liquid chromatography and the sample differences were estimated. The differences in the polyphenol content in the green lettuce cultivars in dependence on fertilisation were much higher than those in the red cultivar. In general, the red lettuce Lolo rosa cv. Tuska was characterised by the highest content of polyphenols. The highest content of all components was determined in the samples of red lettuce with the use of organic fertiliser Arkobaleno. In. the red lettuce and the green lettuce cv. Winter Butterhead organic fertilisation resulted in the higher content of polyphenols in comparison with mineral fertilisation and unfertilised samples. An exception was observed in cv. Maritima, where the unfertilised samples showed higher content of polyphenols compared to the fertilised samples

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.

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.

N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide was prepared by a reaction between 2,2-diphenylethan-1-amine and naproxen in high yield. The newly obtained naproxen derivative was fully analyzed and characterized via 1H, 13C, UV, IR, 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.

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.

N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between tryptamine and flurbiprofen, applying N,N’-Dicyclohexylcarbodiimide, as a coupling agent. The obtained new amide has a fragment similar to Brequinar, a compound used in SARS-CoV-2 treatment trials. The newly synthesized compound was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data.

The titular compound was prepared by a reaction between tryptamine and carprofen, applying, as a “dehydrating” reagent, N,N’-dicyclohexylcarbodiimide. The newly synthesized compound was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data.