Comparison of HPLC, HPTLC, and In Silico Lipophilicity Parameters Determined for 5-Heterocyclic 2-(2,4-Dihydroxyphenyl)-1,3,4-thiadiazoles

The 5-heterocyclic 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles were obtained as potential biologically active compounds. Lipophilicity is one of the most important physicochemical properties of compounds and was already taken into account during the drug candidates design and development. The lipophi...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2024-06, Vol.29 (11), p.2478
Main Authors: Paw, Beata, Śliwa, Rafał, Komsta, Łukasz, Senczyna, Bogusław, Karpińska, Monika, Matysiak, Joanna
Format: Article
Language:English
Subjects:
Antifungal agents
Cancer
Chromatography
Chromatography, High Pressure Liquid - methods
Chromatography, Reverse-Phase - methods
Chromatography, Thin Layer - methods
Computer Simulation
Heterocyclic compounds
High performance liquid chromatography
Hydrophobic and Hydrophilic Interactions
liquid chromatography
log kw
log P
PCA
Retention
RMw
Solvents
thiadiazoles
Thiadiazoles - chemistry
Toxicity
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Summary:The 5-heterocyclic 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles were obtained as potential biologically active compounds. Lipophilicity is one of the most important physicochemical properties of compounds and was already taken into account during the drug candidates design and development. The lipophilicity of compounds was determined using the computational (log P) and chromatography (log k , R ) methods. The experimental ones included the reverse-phase column high performance liquid chromatography RP (HPLC) with C8, C18, phosphatidylcholine (IAM), and cholesterol stationary phases and the thin layer chromatography (RP-HPTLC) with C8 and C18 stationary phases and various organic modifiers under the isocratic conditions. Descriptive statistics, correlation, and PCA analyses were used to compare the obtained results. For lipophilicity estimation of the tested compounds by HPTLC, dioxane and MeOH seem to be particularly beneficial as organic modifiers. The chromatographic lipophilicity parameters log k (R ) were well correlated and highly redundant (85%) compared with those calculated. Most compounds possess lipophilicity parameters within the recommended range for drug candidates.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29112478