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Abstract
A new series of acetamide derivatives containing 1,2,4-triazole and azinane moieties has been synthesized and characterized using $^{1}$H NMR, $^{13}$C NMR, IR, and EI-MS spectroscopic analysis. The intermediate triazole was synthesized through a sequential synthesis of carboxylate and carbohydrazide. The bovine serum albumin (BSA) binding of the newly synthesized 1,2,4-triazole derivatives was evaluated along with thermodynamics, site-selective binding, and synchronous study. The results obtained by BSA binding as well as thermodynamic studies justify that all the compounds show spontaneous interaction with BSA and could be effectively distributed and eliminated from the body. Therefore, the triazole-based analogs might be a useful strategy for designing new drug systems.
Highlights
Proteins are the most abundant macromolecules in cells and play a vital role in maintaining normal cell functions, which are in turn responsible for the origin, evolution, and metabolism of life
IQBAL et al./Turk J Chem ligand binding sites on bovine serum albumin (BSA) are located in subdomains IIA and IIIA, namely site I and site II
It has been reported that some small molecules including hybrids based on azole heterocyclic systems bind exclusively to specific sites, either to the tryptophan residue or to the tyrosine residue on BSA molecules. 2
Summary
Proteins are the most abundant macromolecules in cells and play a vital role in maintaining normal cell functions, which are in turn responsible for the origin, evolution, and metabolism of life. N -(substituted)-2-(5-(1-(4-nitrophenylsulfonyl)piperidin-4-yl)-4-phenyl-4H -1,2,4-triazol-3-ylthio)acetamides (8a–8i; Table 1; Scheme) were synthesized in good yield. Thermodynamics of BSA binding The interactions between the triazole compounds and BSA may involve hydrophobic, electrostatic, or van der Waals forces as well as hydrogen bonding.
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