Synthesis, Structural Studies and Biological Evaluation of Connections of Thiosemicarbazide, 1,2,4-Triazole and 1,3,4-Thiadiazole with Palmitic Acid

Molecules

Michał Jóźwiak¹  Małgorzata Wrzosek¹  Grażyna Kubiak-Tomaszewska¹  Wioletta Olejarz¹  Wojciech Filipowski²  Anna Filipowska³  Marta Struga⁴  Karolina Stępień⁴ 

[1] Department of Biochemistry and Pharmacogenomics, Faculty of Pharmacy, Medical University of Warsaw, 02-097 Warsaw, Poland;Department of Biosensors and Processing of Biomedical Signals, Silesian University of Technology, 44-800 Zabrze, Poland;Faculty of Automatic Control, Electronics and Computer Science, Silesian University of Technology, 44-100 Gliwice, Poland;Laboratory of Centre for Preclinical Research, Medical University of Warsaw, 02-097 Warsaw, Poland;

关键词: palmitic acid derivatives;    thiosemicarbazides;    1,2,4-triazoles;    1,3,4-thiadiazoles;    antimicrobial activity;    quantitative structure-activity relationship;   

DOI  :  10.3390/molecules23040822

来源: DOAJ

【 摘 要 】

Thirty new derivatives of palmitic acid were efficiently synthesized. All obtained compounds can be divided into three groups of derivatives: Thiosemicarbazides (compounds 1–10), 1,2,4-triazoles (compounds 1a–10a) and 1,3,4-thiadiazoles (compounds 1b–10b) moieties. 1H-NMR, 13C-NMR and MS methods were used to confirm the structure of derivatives. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. Compounds 4, 5, 6, 8 showed significant inhibition against C. albicans. The range of MIC values was 50–1.56 μg/mL. The halogen atom, especially at the 3rd position of the phenyl group was significantly important for antifungal activity. The biological activity against Candida albicans and selected molecular descriptors were used as a basis for QSAR models, that have been determined by means of multiple linear regression. The models have been validated by means of the Leave-One-Out Cross Validation. The obtained QSAR models were characterized by high determination coefficients and good prediction power.

【 授权许可】

Unknown