Microwave-assisted synthesis of 1,2,3,4-tetrahydroisoquinoline sulfonamide derivatives and their biological evaluation

Manolov, P Stanimir; Ivanov, Iliyan; Bojilov, G Dimitar

doi:10.2298/jsc200802076m

Cited by 8 publications

(9 citation statements)

References 28 publications

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“…The ability of ibuprofen derivatives to scavenge hydrogen peroxide was assessed according to the method reported by Ruch [34] with minor modification as described by Manolov et al [35]. The solution of hydrogen peroxide (43 mM) was prepared in potassium phosphate-buffered solution (0.2 M, pH 7.4).…”

Section: Biological Experimentsmentioning

confidence: 99%

“…In vitro analysis of anti-inflammatory activity was assessed as inhibition of albumin denaturation (IAD). The analysis was performed according Sakat method [36] with minor modification [35]. The experiment was performed with human albumin.…”

Section: Inhibition Of Albumin Denaturation (Iad)mentioning

confidence: 99%

“…This method is known also as an in vitro anti-arthritic activity. The analysis was performed according to the method of Oyedapo and Femurewa [27] with minor modification as described by Manolov et al [35]. The reaction mixture was containing 2 mL 0.06 mg/mL trypsin, 1 mL Tris-HCl buffer (20 mM, pH 7.4) and 1 mL test sample/standard (in methanol) of different concentrations (20-1000 µg/mL).…”

Section: Antitryptic Activity (Ata)mentioning

confidence: 99%

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Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

Manolov

Ivanov

Bojilov

2022

Molbank

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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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Section: Biological Experimentsmentioning

confidence: 99%

Section: Inhibition Of Albumin Denaturation (Iad)mentioning

confidence: 99%

Section: Antitryptic Activity (Ata)mentioning

confidence: 99%

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Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

Manolov

Ivanov

Bojilov

2022

Molbank

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“…The in vitro anti-inflammatory activity was assessed via the inhibition of albumin denaturation ( IAD ). The analysis was performed according to the Manolov method [ 57 ] with minor modification. The experiment was performed with human albumin.…”

Section: Methodsmentioning

confidence: 99%

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

Bojilov,

Manolov,

Nacheva

et al. 2023

Molecules

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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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“…In vitro, analysis of anti-inflammatory activity was assessed as inhibition of albumin denaturation (IAD). The analysis was performed according to Manolov et al method [18] with minor modifications. The experiment was performed with human albumin.…”

Section: Inhibition Of Albumin Denaturation (Iad)mentioning

confidence: 99%

Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles

Manolov,

Bojilov,

Ivanov

et al. 2023

Processes

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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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Microwave-assisted synthesis of 1,2,3,4-tetrahydroisoquinoline sulfonamide derivatives and their biological evaluation

Cited by 8 publications

References 28 publications

Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

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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