Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property

Kundu, Tania; Pramanik, Animesh

doi:10.1016/j.bioorg.2020.103734

Cited by 33 publications

(15 citation statements)

References 29 publications

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“…Nonetheless, the foremost synthetic challenge in this field is to design and synthesize new polytopic ligands with appropriate donor groupings placed strategically in place for metal coordination. In general, pyrrole, thiophene, and their organic and metal cluster derivatives are recognized to present a wide range of biological activities [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. Therefore, the design and synthesis of novel ligands containing the thiophene and pyrrole rings have attracted great interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1E)-1-(thiophen-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L1) and N’2, N’6-bis[(1E)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2, 6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, 1H, and 13C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311+ G (d, p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of ∆H, ∆S, and ∆G for both the ligands. The optimized vibrational frequency and (1H and 13C) NMR obtained by B3LYP/cc-pvdz/6-311 + G (d, p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from Bacillus megaterium. The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against Bacillus megaterium with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol−1, respectively, with tyrosinase from Bacillus megaterium.‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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“…A study by de La Cruz et al 17 showed the role of the catechol group in the antioxidant and neuroprotective effect of olive oil in the rat brain. More interestingly, a synthetic derivative of cyclohexane carrying cyclohexane 1,3-dione was observed for reducing power 18 . Pyrogallol is one of those compounds found in methanol extract and ethyl acetate and butanol fractions.…”

Section: Resultsmentioning

confidence: 99%

Chemical Compositions and Antioxidant Activities of Flower Extracts from Chestnut (Castanea crenata Sieb. et Zucc)

Tuyen¹,

Trang²,

Khang³

et al. 2023

Asian J. of Plant Sciences

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Background and Objective: Castanea crenata Sieb. et Zucc is a native species in Japan (Japanese chestnut). This species was reported to have very high antioxidant, allergic and anti-amnesic properties. The objective of the study was to evaluate the total polyphenols and antioxidant activities and analyse the bioactive compounds of this species. Materials and Methods: The flower of C. crenata was extracted by methanol and then the crude extract was fractioned by hexane, ethyl acetate, butanol and aqueous extracts. The extract and fractions were used to determine total polyphenols and antioxidant activities and to analyze bioactive components by gas chromatography-mass spectrometry (GC-MS). Results: The hexane fraction showed the highest amount of phenolic, flavonoid and tannin contents. This fraction also exhibited a higher reducing power at a concentration of 1 mg mLG 1 than the other fractions and standard compound BHT (butylated hydroxytoluene). Methanol extract possessed the highest antioxidant capacity and significant stronger than BHT (p<0.05) in DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS [2,2 -azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) methods. Significantly positive correlations were observed between phenolic and tannin contents and reducing power with r = 0.76 and 0.63, respectively. By gas chromatography-mass spectrometry (GC-MS) analysis, 64 components were detected in the C. crenata flower.Methanol and ethyl acetate were found the highest number of compounds with 24 while butanol and water fractions included 20 compounds. The lowest number of constituents were identified in hexane with 7 compounds. Conclusion: Methanol and ethyl acetate were the most effective solvent to extract phytochemicals in the C. crenata flower, followed by butanol and water and hexane showed the least efficacy.

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“…17 In addition, research papers have described good antioxidant capacities of the pyrrole moiety, with particular attention given to the multi-functionalized pyrrole rings. 18,19 Considering the aforementioned observations, we designed and synthesized one multisubstituted pyrrole molecule, its corresponding hydrazide, and four hydrazide-hydrazones containing electron donating groups. A tryptophan motif was also present in the title molecules considering its antioxidant capacity.…”

Section: Design and Synthesis Of Pyrrole Analoguesmentioning

confidence: 99%

Design, microwave-assisted synthesis, biological evaluation, molecular docking and ADME studies of pyrrole-based hydrazide-hydrazones as potential antioxidant agents

Mateev¹,

Georgieva²,

Zlatkov³

2022

Maced. J. Chem. Chem. Eng.

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In this study, one novel N-pyrrolyl carboxylic acid (3), the corresponding N-pyrrolyl hydrazide (5), and four new hydrazide-hydrazones (5a-d) bearing electron donating moieties were designed, synthesized, and fully elucidated by 1H NMR, FT-IR, and HRMS. The hydrazide-hydrazones were produced in five steps, which were optimized by applying microwave heating. The microwave-assisted synthesis significantly decreased the reaction times and increased the yields of the title molecules. In addition, all novel compounds were assessed for their radical scavenging properties by employing DPPH and ABTS assays. The most promising agent was obtained after condensation of the title hydrazide (5) with a 3,5-dimetoxy-4-hydroxybenzaldehyde (5d). The latter compound showed better antioxidant properties than Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and could serve as a prominent lead structure for future optimization as an antioxidant agent. A possible binding conformation of 5d in the active site of NADPH oxidase was also identified through molecular docking simulations. Analysis of the major interactions showed the importance of the hydroxyl moiety for the antioxidant activity. Finally, the virtual calculations of the ADME properties of the synthesized compounds displayed good drug-like properties. Overall, an optimized synthetic protocol through MW irradiation was employed. The newly synthesized ethyl (E)-5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazineyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (5d) was found to possess the most prominent radical-scavenging capacity, which identifies it as a promising lead compound for the development of novel antioxidants.

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Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property

Cited by 33 publications

References 29 publications

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Chemical Compositions and Antioxidant Activities of Flower Extracts from Chestnut (Castanea crenata Sieb. et Zucc)

Design, microwave-assisted synthesis, biological evaluation, molecular docking and ADME studies of pyrrole-based hydrazide-hydrazones as potential antioxidant agents

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