Heterocycles 52: The Drug-Likeness Analysis of Anti-Inflammatory Thiazolo[3,2-b][1,2,4]triazole and Imidazo[2,1-b][1,3,4]thiadiazole Derivatives.

ADME properties POM analysis RP-TLC bioactivity imidazo[2,1-b][1,3,4]thiadiazoles lipophilicity thiazolo[3,2-b][1,2,4]triazoles

Journal

Pharmaceuticals (Basel, Switzerland)
ISSN: 1424-8247
Titre abrégé: Pharmaceuticals (Basel)
Pays: Switzerland
ID NLM: 101238453

Informations de publication

Date de publication:
25 Feb 2024
Historique:
received: 10 01 2024
revised: 16 02 2024
accepted: 23 02 2024
medline: 28 3 2024
pubmed: 28 3 2024
entrez: 28 3 2024
Statut: epublish

Résumé

Lipophilicity, a significant physicochemical parameter of bioactive molecules, along with absorption, distribution, metabolism, excretion parameters and toxicity risk, was investigated for 32 thiazolo[3,2-b][1,2,4]triazole and imidazo[2,1-b][1,3,4]thiadiazole derivatives with anti-inflammatory potential. The experimental lipophilicity study was carried out by reversed-phase thin-layer chromatography in a binary isopropanol-water mobile phase, and the obtained results were compared with the theoretical lipophilicity parameters estimated by various computational methods. Strong correlations were found between the experimental retention factors and calculated partition coefficients. A modified Petra/Osiris/Molinspiration analysis was performed on the previously synthesized compounds, using SwissADME, Osiris and Molinspiration web tools. The predicted in silico parameters highlighted the most promising compounds as potential drug candidates. The compounds showed good gastrointestinal absorption, moderate activity according to the bioactivity score (values situated between -1.25 and -0.06), and a safe toxicity profile. The results obtained in this study will contribute to lipophilicity studies and other future studies focused on modulating new drug candidates starting from thiazolo[3,2-b][1,2,4]triazole and imidazo[2,1-b][1,3,4]thiadiazole derivatives, which are important heterocycles in medicinal chemistry.

Identifiants

pubmed: 38543081
pii: ph17030295
doi: 10.3390/ph17030295
pii:
doi:

Types de publication

Journal Article

Langues

eng

Auteurs

Anamaria Apan (A)

Department of Pharmacology, Physiology and Pathophysiology, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 6A Louis Pasteur Street, 400349 Cluj-Napoca, Romania.

Dorina Casoni (D)

Department of Chemistry, Faculty of Chemistry and Chemical Engineering, "Babeş-Bolyai" University, 11 Arany János Street, 400028 Cluj-Napoca, Romania.

Denisa Leonte (D)

Department of Organic Chemistry, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 41 Victor Babeș Street, 400012 Cluj-Napoca, Romania.

Cristina Pop (C)

Department of Pharmacology, Physiology and Pathophysiology, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 6A Louis Pasteur Street, 400349 Cluj-Napoca, Romania.

Irina Iaru (I)

Department of Pharmacology, Physiology and Pathophysiology, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 6A Louis Pasteur Street, 400349 Cluj-Napoca, Romania.

Cristina Mogoșan (C)

Department of Pharmacology, Physiology and Pathophysiology, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 6A Louis Pasteur Street, 400349 Cluj-Napoca, Romania.

Valentin Zaharia (V)

Department of Organic Chemistry, Faculty of Pharmacy, "Iuliu Hațieganu" University of Medicine and Pharmacy, 41 Victor Babeș Street, 400012 Cluj-Napoca, Romania.

Classifications MeSH