40 results on '"Dimitar Bojilov"'
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2. Chemical composition and biological activity of essential oil from anise hyssop
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Silviya Mollova, Stanko Stanev, Dimitar Bojilov, Stanimir Manolov, Iliana Kostova, Stanka Damianova, Hafize Fidan, Albena Stoyanova, Sezai Ercisli, Amine Assouguem, Riaz Ullah, and Ahmed Bari
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Agastache foeniculum ,essential oil ,chemical composition ,antimicrobial activity ,antioxidant activity ,Biotechnology ,TP248.13-248.65 - Abstract
AbstractAnise 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.
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- 2024
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3. (±)-R,S-2-Chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide
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Diyana Dimitrova, Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov, and Paraskev Nedialkov
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amide ,7-amino-4-methyl-2H-chromen-2-one ,(±)-2-chloro-2-phenylacetyl chloride ,in vitro ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2024
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4. N-(3-chlorophenethyl)-4-nitrobenzamide
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Diyana Dimitrova, Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov, and Paraskev Nedialkov
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amide ,4-nitrobenzoyl chloride ,2-(3-chlorophenyl)ethan-1-amine ,hybrid molecule ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2024
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5. N-(2,2-Diphenylethyl)-4-nitrobenzamide
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Diyana Dimitrova, Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, Lyusi Kasamova, and Paraskev Nedialkov
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mechanochemistry ,ball mill ,2,2-diphenylethan-1-amine ,4-nitrobenzoyl chloride ,amide ,hybrid molecule ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2024
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6. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, and Paraskev Nedialkov
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7-amino-4-methyl-coumarin ,(±)-flurbiprofen ,amide ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2023
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7. (±)-N-(1,2-Bis(3,4-dimethoxyphenyl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
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Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov, and Paraskev Nedialkov
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1,2-bis(3,4-dimethoxyphenyl)ethan-1-amine ,(±)-flurbiprofen ,amide ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2023
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8. Novel Flurbiprofen Derivatives as Antioxidant and Anti-Inflammatory Agents: Synthesis, In Silico, and In Vitro Biological Evaluation
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Iliyan Ivanov, Stanimir Manolov, Dimitar Bojilov, Gabriel Marc, Diyana Dimitrova, Smaranda Oniga, Ovidiu Oniga, Paraskev Nedialkov, and Maria Stoyanova
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flurbiprofen ,2-phenethylamines ,amides ,synthesis ,in vitro ,in silico ,Organic chemistry ,QD241-441 - Abstract
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.
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- 2024
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9. (±)-N-(3-Chlorophenethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, and Gabriela Nikolova
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naproxen ,amide ,2-(3-chlorophenyl)ethan-1-amine ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2023
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10. HPLC Analysis and In Vitro and In Silico Evaluation of the Biological Activity of Polyphenolic Components Separated with Solvents of Various Polarities from Helichrysum italicum
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Dimitar Bojilov, Stanimir Manolov, Sezan Ahmed, Soleya Dagnon, Iliyan Ivanov, Gabriel Marc, Smaranda Oniga, Ovidiu Oniga, Paraskev Nedialkov, and Silviya Mollova
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Helichrysum italicum ,HPSA ,HRSA ,MChA ,NOSA ,IAD ,Organic chemistry ,QD241-441 - Abstract
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).
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- 2023
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11. N-(3-Chlorophenethyl)-2-(4-isobutylphenyl)propanamide
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Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, and Yolina Kalinova
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amide ,ibuprofen ,2-phenylethylamine ,chlorine ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2022
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12. Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity
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Dimitar Bojilov, Stanimir Manolov, Angelika Nacheva, Soleya Dagnon, and Iliyan Ivanov
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Chenopodium botrys ,in vitro biological activity ,HPSA ,HRSA ,NOSA ,IAD ,Organic chemistry ,QD241-441 - Abstract
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).
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- 2023
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13. Polyphenol composition of lettuce cultivars affected by mineral and bio-organic fertilisation
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Dimitar Bojilov, Soleya Dagnon, Kostadin Kostadinov, and Stoyan Filipov
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lactuca sativa ,organic and bio fertilisers ,hplc-pda ,Agriculture - Abstract
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
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- 2020
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14. Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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quinoline ,ibuprofen ,hybrid molecule ,in silico ,in vitro ,antioxidant ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2022
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15. (±)-2-(2-Fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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amphetamine ,flurbiprofen ,DCC ,amide ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2022
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16. Synthesis, In Vitro Anti-Inflammatory Activity, and HRMS Analysis of New Amphetamine Derivatives
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Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, and Paraskev Nedialkov
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amphetamine ,ibuprofen ,flurbiprofen ,ketoprofen ,naproxen ,carprofen ,Organic chemistry ,QD241-441 - Abstract
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.
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- 2022
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17. N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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2,2-diphenylethylamine ,naproxen ,DCC ,amide ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2021
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18. N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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benzo[d]thiazol-2-amine ,flurbiprofen ,DCC ,amide ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2021
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19. N-(2-(1H-Indol-3-yl)ethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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amide ,naproxen ,SARS-CoV-2 ,tryptamine ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2021
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20. N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
- Author
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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amide ,flurbiprofen ,SARS-CoV-2 ,tryptamine ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2020
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21. N-(2-(1H-indol-3-yl)ethyl)-2-(6-chloro-9H-carbazol-2-yl)propanamide
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Stanimir Manolov, Iliyan Ivanov, and Dimitar Bojilov
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amide ,carprofen ,tryptamine ,Inorganic chemistry ,QD146-197 - Abstract
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.
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- 2020
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22. Chemical Composition of Essential Oils from Nepeta transcaucasica Grossh. and Nepeta cataria L. Cultivated in Bulgaria and Their Antimicrobial and Antioxidant Activity
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Silviya Mollova, Anatoli Dzhurmanski, Hafize Fidan, Dimitar Bojilov, Stanimir Manolov, Ivayla Dincheva, Stanko Stankov, Albena Stoyanova, Sezai Ercisli, Amine Assouguem, Romina Alina Marc, Riaz Ullah, and Ahmed Bari
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General Chemical Engineering ,General Chemistry - Published
- 2023
23. Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles
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Nedialkov, Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov, Gabriel Marc, Nadezhda Bataklieva, Smaranda Oniga, Ovidiu Oniga, and Paraskev
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ketoprofen ,pyrrolidine ,piperidine ,1,2,3,4-tetrahydroquinoline ,1,2,3,4-tetrahydroisoquinoline ,hybrid molecules ,in vitro biological activity ,molecular docking ,molecular dynamics - Abstract
Herein, we report the synthesis of four new hybrid molecules between ketoprofen or 2-(3-benzoylphenyl)propanoic acid and N-containing heterocyclic compounds, such as piperidine, pyrrolidine, 1,2,3,4-tetrahydroquinoline, and 1,2,3,4-tetrahydroisoquinoline. The obtained hybrid compounds were fully characterized using 1H- and 13C-NMR, UV-Vis, and HRMS spectra. Detailed HRMS analysis is provided for all novel hybrid molecules. The compounds were assessed for their in vitro anti-inflammatory and antioxidant activity. The lipophilicity of the hybrids was determined, both theoretically (cLogP) and experimentally (RM). The affinity of the compounds to the human serum albumin was assessed in silico by molecular docking study using two software, and the stability of the predicted complexes was evaluated by molecular dynamics study. All novel hybrids have shown very good HPSA activity, statistically close when compared to the reference—quercetin. The molecular docking confirmed the obtained in vitro results. Tetrahydroquinoline derivative 3c and tetrahydroisoquinoline derivative 3d have the highest affinity for albumin. They show stronger anti-inflammatory action than their predecessor, ketoprofen and the regularly used ibuprofen.
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- 2023
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24. Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity
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Ivanov, Dimitar Bojilov, Stanimir Manolov, Angelika Nacheva, Soleya Dagnon, and Iliyan
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Chenopodium botrys ,in vitro biological activity ,HPSA ,HRSA ,NOSA ,IAD ,ATA ,flavonoid-glycosides ,6-methoxy and polymethoxylated flavones - Abstract
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).
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- 2023
- Full Text
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25. Synthesis, In Vitro Anti-Inflammatory Activity, and HRMS Analysis of New Amphetamine Derivatives
- Author
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Dimitar Bojilov, Iliyan Ivanov, Stanimir Manolov, and Paraskev Nedialkov
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amphetamine ,ibuprofen ,flurbiprofen ,ketoprofen ,naproxen ,carprofen ,amides ,HRMS ,amfens ,in vitro ,toxicity ,Chemistry (miscellaneous) ,Organic Chemistry ,Drug Discovery ,Molecular Medicine ,Pharmaceutical Science ,Physical and Theoretical Chemistry ,Analytical Chemistry - Abstract
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.
- Published
- 2022
26. Microwave-assisted synthesis of 1,2,3,4-tetrahydroisoquinoline sulfonamide derivatives and their biological evaluation
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I Iliyan Ivanov, P Stanimir Manolov, and G Dimitar Bojilov
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inhibition of albumin denaturation ,chemistry.chemical_classification ,Antioxidant ,Chemistry ,Tetrahydroisoquinoline ,medicine.medical_treatment ,Albumin ,General Chemistry ,h2o2 scavenging activity ,antitryptic activity ,Combinatorial chemistry ,Thin-layer chromatography ,microwave synthesis ,Sulfonamide ,lcsh:Chemistry ,chemistry.chemical_compound ,antibacterial activity ,lcsh:QD1-999 ,Lipophilicity ,medicine ,Denaturation (biochemistry) ,sio2/ppa ,Antibacterial activity - Abstract
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.
- Published
- 2021
27. Polyphenol composition of lettuce cultivars affected by mineral and bio-organic fertilisation
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S. Dagnon, Stoyan Filipov, Dimitar Bojilov, and Kostadin Kostadinov
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Horticulture ,Mineral ,Chemistry ,Polyphenol ,Composition (visual arts) ,Cultivar ,Fertilisation ,Food Science - Published
- 2020
28. N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
- Author
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Dimitar Bojilov, Stanimir Manolov, and Iliyan Ivanov
- Subjects
Tryptamine ,Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) ,Flurbiprofen ,Biochemistry ,Medicinal chemistry ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Amide ,medicine ,lcsh:Inorganic chemistry ,Physical and Theoretical Chemistry ,Spectral data ,030304 developmental biology ,Biphenyl ,0303 health sciences ,SARS-CoV-2 ,Organic Chemistry ,Propanamide ,amide ,lcsh:QD146-197 ,flurbiprofen ,chemistry ,030220 oncology & carcinogenesis ,tryptamine ,medicine.drug - Abstract
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.
- Published
- 2021
29. Synthesis, In Silico, and In Vitro Biological Evaluation of New Furan Hybrid Molecules
- Author
-
Dimitar Bojilov, Iliyan Ivanov, Stanimir Manolov, and Paraskev Nedialkov
- Subjects
Process Chemistry and Technology ,furan ,1,2,3,4-tetrahidroquinoline ,1,2,3,4-tetrahidroisoquinoline ,piperidine ,pyrrolidine ,in silico ,in vitro biological activity ,Chemical Engineering (miscellaneous) ,Bioengineering - Abstract
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.
- Published
- 2022
30. N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
- Author
-
Dimitar Bojilov, Iliyan Ivanov, and Stanimir Manolov
- Subjects
Naproxen ,Organic Chemistry ,Biochemistry ,Propanamide ,Medicinal chemistry ,amide ,chemistry.chemical_compound ,chemistry ,Amide ,Yield (chemistry) ,medicine ,2,2-diphenylethylamine ,naproxen ,Physical and Theoretical Chemistry ,Spectral data ,Derivative (chemistry) ,Inorganic chemistry ,medicine.drug ,DCC ,QD146-197 - Abstract
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.
- Published
- 2021
31. Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation
- Author
-
Dimitar Bojilov, Iliyan Ivanov, and Stanimir Manolov
- Subjects
Organic Chemistry ,Physical and Theoretical Chemistry ,Biochemistry - Abstract
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.
- Published
- 2022
32. N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
- Author
-
Dimitar Bojilov, Iliyan Ivanov, and Stanimir Manolov
- Subjects
Biphenyl ,010405 organic chemistry ,Organic Chemistry ,Flurbiprofen ,010402 general chemistry ,amide ,01 natural sciences ,Biochemistry ,Propanamide ,Medicinal chemistry ,flurbiprofen ,0104 chemical sciences ,benzo[d]thiazol-2-amine ,chemistry.chemical_compound ,chemistry ,Amide ,Yield (chemistry) ,medicine ,Physical and Theoretical Chemistry ,Spectral data ,Inorganic chemistry ,Derivative (chemistry) ,DCC ,QD146-197 ,medicine.drug - Abstract
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.
- Published
- 2021
33. New insight into the flavonoid composition of Chenopodium botrys
- Author
-
Iliyan Ivanov, Dimitar Bojilov, and S. Dagnon
- Subjects
0106 biological sciences ,chemistry.chemical_classification ,Chromatography ,Eupatilin ,Flavonoid ,Plant Science ,01 natural sciences ,Biochemistry ,Flavones ,Nobiletin ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Rutin ,chemistry ,Polyphenol ,medicine ,Quercetin ,Agronomy and Crop Science ,Nepetin ,010606 plant biology & botany ,Biotechnology ,medicine.drug - Abstract
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.
- Published
- 2017
34. N-(2-(1H-Indol-3-yl)ethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
- Author
-
Iliyan Ivanov, Stanimir Manolov, and Dimitar Bojilov
- Subjects
Tryptamine ,2019-20 coronavirus outbreak ,Naproxen ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Amide ,lcsh:Inorganic chemistry ,medicine ,naproxen ,Physical and Theoretical Chemistry ,Spectral data ,SARS-CoV-2 ,010401 analytical chemistry ,Organic Chemistry ,amide ,Propanamide ,lcsh:QD146-197 ,0104 chemical sciences ,chemistry ,Yield (chemistry) ,tryptamine ,030217 neurology & neurosurgery ,Derivative (chemistry) ,medicine.drug - Abstract
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.
- Published
- 2021
35. Determination and discrimination of biodiesel fuels by gas chromatographic and chemometric methods
- Author
-
Z. Mustafa, Dimitar Bojilov, R. Milina, M. Moskovkina, and S. Dagnon
- Subjects
Pulmonary and Respiratory Medicine ,Biodiesel ,Animal fat ,Geography (General) ,Chemistry ,020209 energy ,gas chromatography ,Science ,02 engineering and technology ,Pulp and paper industry ,biodiesel fuel ,Vegetable oil ,vegetable oil ,0202 electrical engineering, electronic engineering, information engineering ,G1-922 ,Pediatrics, Perinatology, and Child Health ,Gas chromatography ,fatty acid methyl esters ,animal fat - Abstract
Pattern recognition method (PRM) was applied to gas chromatographic (GC) data for a fatty acid methyl esters (FAME) composition of commercial and laboratory synthesized biodiesel fuels from vegetable oils including sunflower, rapeseed, corn and palm oils. Two GC quantitative methods to calculate individual fames were compared: Area % and internal standard. The both methods were applied for analysis of two certified reference materials. The statistical processing of the obtained results demonstrates the accuracy and precision of the two methods and allows them to be compared. For further chemometric investigations of biodiesel fuels by their FAME-profiles any of those methods can be used. PRM results of FAME profiles of samples from different vegetable oils show a successful recognition of biodiesels according to the feedstock. The information obtained can be used for selection of feedstock to produce biodiesels with certain properties, for assessing their interchangeability, for fuel spillage and remedial actions in the environment.
- Published
- 2016
36. The Relationship between Main Polyphenol Components and Free Radical Scavenging Activity of Selected Medicinal Plants
- Author
-
Dimitar Bojilov, Margarita Docheva, S. Dagnon, and A. Edreva
- Subjects
chemistry.chemical_classification ,Achillea millefolium ,biology ,010405 organic chemistry ,DPPH ,Rosmarinic acid ,Glycoside ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,chemistry ,Polyphenol ,Apigenin ,Food science ,Luteolin ,Artemisia vulgaris - Abstract
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.
- Published
- 2018
37. Antioxidant defense during desiccation of the resurrection plant Haberlea rhodopensis
- Author
-
Gergana Mihailova, Snezhana Doncheva, Dimitar Bojilov, S. Dagnon, E. Gesheva, and Katya Georgieva
- Subjects
0106 biological sciences ,0301 basic medicine ,Ascorbate glutathione cycle ,Antioxidant ,Light ,Physiology ,medicine.medical_treatment ,ved/biology.organism_classification_rank.species ,Resurrection plant ,Plant Science ,Ascorbic Acid ,Biology ,01 natural sciences ,Antioxidants ,Desiccation tolerance ,03 medical and health sciences ,chemistry.chemical_compound ,Magnoliopsida ,Ascorbate Peroxidases ,Botany ,Genetics ,medicine ,Bulgaria ,Haberlea ,Glutathione Transferase ,Plant Proteins ,Dehydration ,ved/biology ,food and beverages ,Polyphenols ,Phenylethanoid ,biology.organism_classification ,Glutathione ,Droughts ,Plant Leaves ,Oxidative Stress ,030104 developmental biology ,Glutathione Reductase ,chemistry ,Polyphenol ,Desiccation ,010606 plant biology & botany - Abstract
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.
- Published
- 2017
38. Development of surrogate standards approach for the determination of polyphenols in Vernonia amygdalina Del
- Author
-
Dimitar Bojilov, Z. Novkova, P. Nedialkov, S. Dagnon, and Ch. Kouassi
- Subjects
chemistry.chemical_classification ,0303 health sciences ,Chromatography ,Achillea ,biology ,030309 nutrition & dietetics ,Vernonia amygdalina ,010401 analytical chemistry ,Glycoside ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,03 medical and health sciences ,Rutin ,chemistry.chemical_compound ,chemistry ,Glucoside ,Polyphenol ,Apigenin ,Luteolin ,Food Science - Abstract
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.
- Published
- 2019
39. Hydroxypyridine Formation In Model System Monosodium Glutamate And 2-Fufural
- Author
-
Dimitar Bojilov
- Subjects
General Medicine - Published
- 2014
40. Chemical composition and antimicrobial and antioxidant activity of Helichrysumitalicum (Roth) G.Don subspecies essential oils
- Author
-
Daniela Antonova, Silviya Mollova, Dimitar Bozhilov, Hafize Fidan, Albena Stoyanova, Stanko Stanev, Iliana Kostova, Dimitar Bojilov, Stanko Stanev, Silviya Mollova, and Hafize Fidan
- Subjects
Antioxidant ,chemical profile ,medicine.medical_treatment ,Monoterpene ,antioxidant activity ,Helichrysum italicum (Roth) G. Don ,Sesquiterpene ,Helichrysum italicum ,law.invention ,chemistry.chemical_compound ,Helichrysum italicum (Roth) G.Don,essential oils,gas chromatography-mass spectrometry,chemical profile,antibacterial,antioxidant activity ,law ,medicine ,Food science ,essential oils ,Essential oil ,Limonene ,Ecology ,biology ,Neryl acetate ,Chemistry ,Forestry ,Antimicrobial ,biology.organism_classification ,Agronomy ,gas chromatography-mass spectrometry ,antibacterial ,Agronomi ,Food Science - Abstract
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.
- Published
- 2020
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