Ferrocenyl based pyrazoline derivatives with vanillic core: synthesis and investigation of their biological properties

Burmudžija, Adrijana; Ratković, Zoran; Muškinja, Jovana; Janković, Nenad; Ranković, Branislav; Kosanić, Marijana; Đorđević, Snežana

doi:10.1039/c6ra18977f

Cited by 24 publications

(11 citation statements)

References 48 publications

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“…Previous studies have also shown that the use of vanillin compounds as starting materials in organic synthesis led to the formation of several vanillin-derivatives with a wide spectrum of biological activities [ 10 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents

et al. 2017

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Novel (E)-1-(aryl)-3-(4-(2-(dimethylamino)ethoxy)-3-methoxyphenyl) prop-2-en-1-ones 4 were synthesized by a Claisen-Schmidt reaction of 4-(2-(dimethylamino)ethoxy)-3-methoxy-benzaldehyde (2) with several acetophenone derivatives 3. Subsequently, cyclocondensation reactions of chalcones 4 with hydrazine hydrate afforded the new racemic 3-aryl-5-(4-(2-(dimethylamino)ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehydes 5 when the reaction was carried out in formic acid. The antifungal activity of both series of compounds against eight fungal species was determined. In general, chalcone derivatives 4 showed better activities than pyrazolines 5 against all tested fungi. None of the compounds 4a–g and 5a–g showed activity against the three Aspergillus spp. In contrast, most of the compounds 4 showed moderate to high activities against three dermatophytes (MICs 31.25–62.5 µg/mL), being 4a followed by 4c the most active structures. Interestingly, 4a and 4c possess fungicidal rather than fungistatic activities, with MFC values between 31.25 and 62.5 μg/mL. The comparison of the percentages of inhibition of C. neoformans by the most active compounds 4, allowed us to know the role played by the different substituents of the chalcones’ A-ring. Also the most anti-cryptococcal compounds 4a–c and 4g, were tested in a second panel of five clinical C. neoformans strains in order to have an overview of their inhibition capacity not only of standardized but also of clinical C. neoformans strains. DFT calculations showed that the electrophilicity is the main electronic property to explain the differences in antifungal activities for the synthesized chalcones and pyrazolines compounds. Furthermore, a quantitative reactivity analysis showed that electron-withdrawing substituted chalcones presented the higher electrophilic character and hence, the greater antifungal activities among compounds of series 4.

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Section: Introductionmentioning

confidence: 99%

Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents

et al. 2017

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“…In medicinal chemistry, 2-pyrazoline acts as a privileged scaffold due to its presence in numerous important medical and biochemical agents that have been effectively utilized as antibacterial, antifungal, anti-inflammatory, analgesic, antiparasitic, antiviral, antitubercular, anticancer, anesthetic, and insecticidal agents. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] Recently, a 4,5-unsaturated pyrazoline ring called pyrazole has marked its versatile use in the drug design, and it has been found to have a remarkable presence in various potential anticancer molecules such as celecoxib, SC5584. Liu et al [23] have confirmed that celecoxib induces apoptosis in the human osteosarcoma cell line and enhances the cytotoxic effect of cisplatin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation, and in silico study of pyrazoline‐conjugated 2,4‐dimethyl‐1H‐pyrrole‐3‐carboxylic acid derivatives

Rasal

Sonawane

Jagtap

2020

Archiv der Pharmazie

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A potential molecular hybridization strategy was used to develop 24 novel pyrazoline‐conjugated 2,4‐dimethyl‐1H‐pyrrole‐3‐carboxylic acid and amide derivatives. The preliminary in vitro antimicrobial assay delivered four potential derivatives with growth inhibition in the range of 50.87–56.60% at the concentration of 32 µg/ml. In the search of an anticancer candidate, all derivatives were screened by NCI‐60 at 10 µM concentration, revealing that 12 derivatives were potential agents against the various types of cancer cell lines, with growth inhibition in the range of 50.21–108.37%. The in vitro cytotoxicity assay against the cell line HEK293 (human embryonic kidney cells) and the hemolysis assay of the representative potent compounds propose their potential for a good therapeutic index. In silico studies of the most potent derivatives qualified their significant pharmacokinetic properties with good predicted oral bioavailability and their adherence to Lipinski's rule of five for druglikeness. A molecular docking study against VEGFR‐2 with the best‐scored conformations reinforced their anticancer potency. The docking study of the most potent compound against VEGFR‐2 with the best‐scored conformations displayed a binding affinity (−9.5 kcal/mol) comparable with the drug sunitinib (−9.9 kcal/mol) and exhibited that tighter interactions at the active adenosine triphosphate site might be responsible for anticancer potency.

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“…Trp134 is in a solvent-exposed region of subdomain IB and is highly accessible, whereas Trp213 is buried in the hydrophobic pocket near the drug binding site in subdomain IIA. Most investigations carried out on the interaction serum albumin with compounds have shown biological activity, which have been reported in the literature [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

The study on the interaction of Epigallocatechin gallate with bovine serum Albumin

Davaadulam

Tamara

Gerelsuren

2020

Proc. Mong. Acad. Sci.

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In this study, we investigated the interaction of epigallocatechin gallate (EGCG) with bovine serum albumin (BSA) by fluorescence method and protein‐ligand docking. We separated EGCG from green tea using the chromatographic method and analyzed structural activity relationships of the EGCG. The results show that EGCG is a strong quencher of BSA fluorescence and binds with BSA with high affinity. The binding parameters (binding constant, the number of binding sites) were determined by the Ward equation. From the thermodynamic parameters, calculated according to the van’t Hoff equation, the enthalpy change ΔH°, and entropy change ΔS° were found to be -22.67 kJ/mol and 14.92 J/mol/K, respectively. These values suggest that apart from an initial hydrophobic association, the complex is held together by electrostatic and hydrogen bonding. In the docking simulation, the lowest free energies for the interaction of EGCG with tryptophan residues was −21.92kJ/mol (Trp134) and −24.7 kJ/mol (Trp213). The binding between EGCG and BSA consists of hydrogen bonds (Trp213) and hydrophobic interactions (Trp134).

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Ferrocenyl based pyrazoline derivatives with vanillic core: synthesis and investigation of their biological properties

Abstract: Synthesis of four novel series of ferrocenyl based pyrazoline derivatives with vanillic core are described and microbiological, BSA and DNA binding studies conducted.

Cited by 24 publications

References 48 publications

Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents

Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents

Synthesis, biological evaluation, and in silico study of pyrazoline‐conjugated 2,4‐dimethyl‐1H‐pyrrole‐3‐carboxylic acid derivatives

The study on the interaction of Epigallocatechin gallate with bovine serum Albumin

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