Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones

Sheikh, Javed; Ali, Parvez; Juneja, Harjeet D.; Ingle, V. N.; Chohan, Zahid H.; Youssoufi, Moulay H.; Hadda, Taïbi Ben

doi:10.1016/j.ejmech.2011.01.068

Cited by 60 publications

(34 citation statements)

References 32 publications

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“…In contrast to antibacterial agent, the antiviral drug should have (X δ--Y δ-) pharmacophore site with respect of some architectural parameters (dihedral angle = 0-10 degree and distance d x-y = 3-3.5 Å). [33][34][35][36][37][38][39] This can be applied for all compounds described here ( Figure 5). …”

Section: 1 Petra Analysismentioning

confidence: 99%

“…Molecular Polar Surface Area PSA is calculated as a sum of fragment contributions. [33][34][35][36][37][38][39] O-, N-and Scentered polar fragments are considered. PSA has been shown to be a very good descriptor characterizing drug absorption, including intestinal absorption, bioavailability, Caco-2 permeability and blood-brain barrier penetration.…”

Section: Molinspiration Calculationsmentioning

confidence: 99%

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Design, Synthesis, in vitro Antiproliferative Activity, Binding Modeling of 1,2,4,-Triazoles as New Anti-Breast Cancer Agents

Genç¹,

Genç²,

Tekin³

et al. 2016

ACSi

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This article demonstrates the synthesis of 1,2,4-triazole derivatives and their applications in medicine particularly as anti-breast cancer agents which is a major issue of the present. The synthesized compounds were characterized by elemental analysis, FT-IR and NMR. DFT was used to study the quantum chemical calculations of geometries and vibrational wave numbers of 3-hydroxynaphthyl and p-tolyl substituted 1,2,4-triazoles in the ground state. The scaled harmonic vibrational frequencies obtained from the DFT method were compared with those of the FT-IR spectra and found good agreement. The synthesized 1,2,4-triazole-naphthyl hybrids were screened for the anticancer activity against MCF-7 breast cancer lines. Among them compounds 3 and 7 showed broad spectrum anticancer activity with IC 50 values 9.7 μM and 7.10 μM, respectively and their activity is comparable to that of the standard drugs. The molecular model for binding between the compounds (1-8) and the active site of BRCA2 was obtained on the basis of the computational docking results and the structure-activity relationship.

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Section: 1 Petra Analysismentioning

confidence: 99%

Section: Molinspiration Calculationsmentioning

confidence: 99%

Design, Synthesis, in vitro Antiproliferative Activity, Binding Modeling of 1,2,4,-Triazoles as New Anti-Breast Cancer Agents

Genç¹,

Genç²,

Tekin³

et al. 2016

ACSi

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“…A suitable theoretical concept is that proposed by Ben Hadda et al [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] apropos of definition of pharmacophore site. The best descriptors for studying and identifying the type of pharmacophore site (antibacterial, antiviral or antitumor) are the description in detail of local electrophilicity and the nucleophilicity of each functionalized group and their spatial arrangement.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13][14][15][16][17][18][19][20][21][22] Recently, it has been shown that the kinase inhibition by an organometallic systems under biological condition may be significantly facilitated if a ligand containing an anti-kinase pharmacophore (NH-C=O), a bidentate N,N coordinative site (staurosporine derivatives) and non-toxic metal (ruthenium) are available. [2][3][4][5][6] The cancer inhibition of kinase enzymes through organic drugs has been the subject of different theoretical investigations.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] For these reasons, we constructed a platform of some of the key bioinformatic model in order to predict and characterize the antitumor drugs performance of the tested series of staurosporine-ruthenium(II) complexes. Our aim in this work is to give a deeper insight into the coordination effect of transition metal (ruthenium) to bioactive drug (staurosporine), on the inhibition efficiency of ruthenium-staurosporine complexes ( Figure 1) using POM and DFT analyses.…”

Section: Introductionmentioning

confidence: 99%

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Computational POM and DFT Evaluation of Experimental in-vitro Cancer Inhibition of Staurosporine-Ruthenium(II) Complexes: The Power Force of Organometallics in Drug Design

Hadda¹,

Genç

Masand³

et al. 2015

ACSi

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A computational Petra/Osiris/Molinspiration/DFT(POM/DFT) based model has been developed for the identification of physico-chemical parameters governing the bioactivity of ruthenium-staurosporine complexes 2-4 containing an antitumoral-kinase (TK) pharmacophore sites. The four compounds 1-4 analyzed here were previously screened for their antitumor activity, compounds 2 and 4 are neutral, whereas analogue compound 3 is a monocation with ruthenium(II) centre. The highest anti-antitumor activity was obtained for compounds 3 and 4, which exhibited low IC 50 values (0.45 and 8 nM, respectively), superior to staurosporine derivative (pyridocarbazole ligand 1, 150 · 10 3 nM). The IC 50 of 3 (0.45 nM), represents 20,000 fold increased activity as compared to staurosporine derivative 1. The increase of bioactivity could be attributed to the existence of pi-charge transfer from metal-staurosporine to its (CO δ--NH δ+ ) antitumor pharmacophore site.

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Biological Investigations of Ru(II) Complexes with Diverse β‐Diketone Ligands

et al. 2021

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The β-diketone scaffold is a commonly used synthetic intermediate, and is a functional group found in natural products such as curcuminoids. This core structure can also act as a chelating ligand for a variety of metals. In order to assess the potential of this scaffold for medicinal inorganic chemistry, seven different k 2 -O,O'-chelating ligands were used to construct Ru(II) complexes with polypyridyl co-ligands, and their biological activity was evaluated. The complexes demonstrated promising structure-dependent cytotoxicity. Three complexes maintained high activity in a tumor spheroid model, and all complexes demonstrated low in vivo toxicity in a zebrafish model. From this series, the best compound exhibited a~30fold window between cytotoxicity in a 3-D tumor spheroid model and potential in vivo toxicity. These results suggest that k 2 -O,O'-ligands can be incorporated into Ru(II)-polypyridyl complexes to create favorable candidates for future drug development.

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Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones

Cited by 60 publications

References 32 publications

Design, Synthesis, in vitro Antiproliferative Activity, Binding Modeling of 1,2,4,-Triazoles as New Anti-Breast Cancer Agents

Design, Synthesis, in vitro Antiproliferative Activity, Binding Modeling of 1,2,4,-Triazoles as New Anti-Breast Cancer Agents

Computational POM and DFT Evaluation of Experimental in-vitro Cancer Inhibition of Staurosporine-Ruthenium(II) Complexes: The Power Force of Organometallics in Drug Design

Biological Investigations of Ru(II) Complexes with Diverse β‐Diketone Ligands

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