Application of different methods to predict the lipophilicity parameter of danazol

2021 ◽  
Vol 77 (10) ◽  
pp. 601-607
Author(s):  
Małgorzata Dołowy ◽  
Rafał Sochacki
Keyword(s):  
Lipophilicity Parameter

scholarly journals Development of TLC Chromatographic-Densitometric Procedure for Qualitative and Quantitative Analysis of Ceftobiprole

Processes ◽  
2021 ◽  
Vol 9 (4) ◽  
pp. 708
Author(s):  
Żaneta Binert-Kusztal ◽  
Małgorzata Starek ◽  
Joanna Żandarek ◽  
Monika Dąbrowska
Keyword(s):  
High Sensitivity ◽  
Biologically Active ◽  
Fifth Generation ◽  
Ich Guidelines ◽  
Relative Standard ◽  
Lipophilicity Parameter ◽  
Alkaline Environments ◽  
Acetic Acid Water ◽  
Cephalosporin Antibiotics ◽  
The Stability

Currently, there is still a need for broad-spectrum antibiotics. The new cephalosporin antibiotics include, among others, ceftobiprole, a fifth-generation gram-positive cephalosporin, active against Staphylococcus aureus methicillin agonist (MRSA). The main focus of the work was to optimize the conditions of ceftobiprole qualitative determination and to validate the developed procedure according to ICH guidelines. As a result of the optimization process, HPTLC Cellulose chromatographic plates as a stationary phase and a mixture consisting of ethanol:2-propanol: glacial acetic acid: water (4:4:1:3, v/v/v/v) as a mobile phase were chosen. The densitometric detection was carried out at maximum absorbance of ceftobiprole (λ = 232 nm). Next, the validation process of the developed procedure was carried out. The relative standard deviation (RSD) for precision was less than 1.65%, which proves the high compatibility of the results, as well as the LOD = 0.0257 µg/spot and LOQ = 0.0779 µg/spot values, which also confirm the high sensitivity of the procedure. The usefulness of the developed method for the stability studies of ceftobiprole was analyzed. Study was carried out under stress conditions, i.e., acid and alkaline environments, exposure to radiation imitating sunlight and high temperature (40–60 °C). It was found that cefotbiprole is unstable in an alkaline environment and during exposure to UV-VIS radiation. Moreover, the lipophilicity parameter, as a main physicochemical property of the biologically active compound, was determined using experimental and computational methods.

scholarly journals Evaluation of the Lipophilicity of New Anticancer 1,2,3-Triazole-Dipyridothiazine Hybrids Using RP TLC and Different Computational Methods

Processes ◽  
2020 ◽  
Vol 8 (7) ◽  
pp. 858
Author(s):  
Beata Morak-Młodawska ◽  
Krystian Pluta ◽  
Małgorzata Jeleń
Keyword(s):  
Computational Methods ◽  
Molecular Descriptors ◽  
Triazole Ring ◽  
Hydrophobic Surface ◽  
Acetone Concentration ◽  
Lipinski’S Rule ◽  
Mobile Phases ◽  
Lipophilicity Parameter ◽  
Lipinski’S Rule Of Five ◽  
Layer Chromatography

Two new anticancer-active 1,2,3-triazole-dipyridothiazine hybrids were evaluated for their lipophilicity using thin-layer chromatography (TLC) and computational methods. The experimental lipophilicity was evaluated with mobile phases (mixtures of TRIS buffer and acetone), exploiting a linear correlation between the retention parameter (RM) and the volume of acetone. The relative lipophilicity parameter (RM0) was obtained by extrapolation to 0% acetone concentration. This parameter was intercorrelated with a specific hydrophobic surface area (b) revealing two congeneric subgroups: hybrids of 1,2,3-triazole-2,7-diazaphenothiazines and 1,2,3-triazole-3,6-diazaphenothiazines. The parameter RM0 was converted into the absolute lipophilicity parameter logPTLC using a calibration curve prepared on the basis of compounds of known logP values. Triazole–dipyridothiazine hybrids turned out to be medium lipophilic with logPTLC values of 1.232–2.979. The chromatographically established parameter logPTLC was compared to the calculated lipophilic parameter logPcalcd obtained with various algorithms. The lipophilicity was correlated with molecular descriptors and ADME properties. The new triazole–dipyridothiazine hybrids followed Lipinski’s rule of five. The lipophilicity of these hybrids was dependent on the substituents attached to the triazole ring and the location of the azine nitrogen atoms.

A structural framework of biologically active coumarin derivatives: crystal structure and Hirshfeld surface analysis

CrystEngComm ◽  
2014 ◽  
Vol 16 (29) ◽  
pp. 6654-6663 ◽  
Author(s):  
Magdalena Małecka ◽  
Elzbieta Budzisz
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Biologically Active ◽  
Hirshfeld Surface Analysis ◽  
Coumarin Derivatives ◽  
Π Interactions ◽  
Structural Framework ◽  
Lipophilicity Parameter

The relation between the lipophilicity parameter (log P) and the contribution of C–H⋯π interactions to the Hirshfeld surface has been investigated.

Bleaching Activity of New 2-Phenylpyridazinones: Structure-Activity Relationship

1982 ◽  
Vol 37 (11-12) ◽  
pp. 1092-1094 ◽  
Author(s):  
Gerhard Sandmann ◽  
Peter Böger
Keyword(s):  
Quantitative Structure Activity Relationship ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Pigment Formation ◽  
Meta Position ◽  
Phytotoxic Activity ◽  
Structure Activity ◽  
Lipophilicity Parameter ◽  
Bleaching Activity ◽  
Plant Pigment

Abstract New 2-phenylpyridazinones, analogs of 4-chloro-5-methylamino-2-phenylpyridazin-3(2H)ones, were assayed for their phytotoxic activity to interfere with plant pigment formation. Six derivatives with - SCF3, - OCF2CHFCF3, - OCHF2, - CN, or - Br in meta position of the phenyl ring exhibited similar or better bleaching activity than the m-CF3 analog (norflurazon). The activity is predominantly determined by positive σ values and by lipophilicity of the substituent. On the basis of 11 analogs, a quantitative structure-activity relationship by a Hansch equation was accomplished with σm and the lipophilicity parameter π as variables.

scholarly journals Correlation between the lipophilicity and antifungal activity of some benzoxazole derivatives

2010 ◽  
pp. 177-185 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Sonja Velimirovic
Keyword(s):  
Antifungal Activity ◽  
Inhibitory Concentration ◽  
Quantitative Relationship ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Biologically Active ◽  
High Agreement ◽  
Structure Activity ◽  
Lipophilicity Parameter ◽  
Office Software

In the present work, a quantitative relationship between the lipophilicity and antifungal activity of some benzoxazole derivatives against Candida albicans was investigated by using QSAR (quantitative structure-activity relationship) analyses. The descriptors which describe numerically the lipophilicity, logP, were calculated using Chem-Office Software version 7.0. The linear correlation between the minimal inhibitory concentration (log1/cMIC) and lipophilicity descriptors was investigated. The best QSAR model predicting the antifungal activity of the investigated series of benzoxazole was developed. The results are discussed on the basis of statistical data. High agreement between theoretical and experimental inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on antifungal activity of this class of compounds, which can be very useful in the design of new biologically active molecules.

scholarly journals Quantitative structure-activity relationship of some 1-benzylbenzimidazole derivatives as antifungal agents

2007 ◽  
pp. 139-147 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Dijana Barna ◽  
Dragoljub Cvetkovic
Keyword(s):  
Antifungal Activity ◽  
Quantitative Structure Activity Relationship ◽  
Structure Activity Relationship ◽  
Biologically Active ◽  
Activity Relationship ◽  
Quantitative Structure ◽  
Yeast Saccharomyces Cerevisiae ◽  
Structure Activity ◽  
Lipophilicity Parameter

In the present study, the antifungal activity of some 1-benzylbenzimidazole derivatives against yeast Saccharomyces cerevisiae was investigated. The tested benzimidazoles displayed in vitro antifungal activity and minimum inhibitory concentration (MIC) was determined for all the compounds. Quantitative structure-activity relationship (QSAR) has been used to study the relationships between the antifungal activity and lipophilicity parameter, logP, calculated by using CS Chem-Office Software version 7.0. The results are discussed on the basis of statistical data. The best QSAR model for prediction of antifungal activity of the investigated series of benzimidazoles was developed. High agreement between experimental and predicted inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on antifungal activity of this class of compounds, which simplify design of new biologically active molecules.

scholarly journals The Application of CA and PCA to the Evaluation of Lipophilicity and Physicochemical Properties of Tetracyclic Diazaphenothiazine Derivatives

2019 ◽  
Vol 2019 ◽  
pp. 1-10
Author(s):  
Anna Nycz–Empel ◽  
Katarzyna Bober ◽  
Mirosław Wyszomirski ◽  
Ewa Kisiel ◽  
Andrzej Zięba
Keyword(s):  
Principal Component ◽  
Biological Properties ◽  
The Other ◽  
Phase System ◽  
Other Hand ◽  
Lipophilicity Parameter ◽  
The Subject ◽  
Experimental Values ◽  
The Relationship ◽  
Layer Chromatography

The subject of the study was 11 new synthetized tetracyclic diazaphenothiazine derivatives. Using thin-layer chromatography in a reverse phase system (RP-TLC), their RM0 lipophilicity parameter was determined. The mobile phase was composed of 0.2 M Tris buffer (pH = 7.4) and acetone (POCH S.A., Gliwice, Poland) in different concentrations. Using computer programs, based on different computational algorithms, theoretical values of lipophilicity (AClogP, ALOGP, ALOGPs, miLogP, MLOGP, XLOGP2, and XLOGP3) as well as molecular descriptors (molecular weight, volume of a molecule, dipole moment, polar surface, and energy of HOMO orbitals and LUMO orbitals) and parameters of biological activity: human intestinal absorption (HIA), plasma protein binding (PPB), and blood-brain barrier (BBB), were determined. The correlations between the experimental values of lipophilicity and theoretically calculated lipophilic values and also between experimental values of lipophilicity and values of physicochemical or biological properties were assessed. A certain relationship between structure and lipophilicity was found. On the other hand, the relationships between RM0 and physicochemical or biological properties were not statistically significant and therefore unusable. For all analysed values, an analysis of similarities and principal component analyses were also made. The obtained dendrograms for the analysis of lipophilicity and physicochemical and biological properties indicate the relationship between experimental values of lipophilicity and structure in the case of theoretical lipophilicity values only. PCA, on the other hand, showed that ALOGP, MLOGP, miLogP, and BBB and molar volume have the largest share in the description of the entire system. Distribution of compounds on the area of factors also indicates the connections between them related to their structure.

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