Adamantane-thiazole hybrids and related derivatives: synthesis, crystal structures, in vitro antibacterial, antifungal, and anti-proliferative activities
Heidi S. Abd El-Monaem, Mahmoud B. El-Ashmawy, Naglaa I. Abdel-Aziz, Olivier Blacque, E. Habib, Subbiah Thamotharan, Ali A. El-Emam
TL;DR
Scientists synthesized adamantane-thiazole compounds that show antibacterial and anti-cancer properties, with some derivatives being effective against specific bacteria and cancer cell lines.
Contribution
The paper introduces new adamantane-thiazole hybrids with demonstrated antibacterial and anti-proliferative activities and confirms their structures using X-ray crystallography.
Findings
Compounds 5a, 5b, 5c, 7a, 7f, 7i, and 7k showed antibacterial activity against S. aureus, B. subtilis, and E. coli.
Compounds 5a, 5b, 5c, 7f, and 7L exhibited anti-proliferative activity against HepG-2 and MCF-7 cancer cells.
Molecular docking studies showed strong binding affinity of some compounds to SaCrtM and uPAR targets.
Abstract
Series of 2-(adamantan-2-ylidene)-N-substituted hydrazine-1-carbothioamide derivatives 5a-d and (E)-2-[(adamantan-2-ylidene)hydrazono]-3,4-diaryl-2,3-dihydrothiazole derivatives 7a-l were prepared and their structures were confirmed. In vitro antimicrobial evaluation of compounds 5a-d and 7a-l against different pathogenic bacterial and fungal strains revealed that compounds 5a, 5b, 5c, 7a, 7f, 7i and 7k displayed notable effectiveness against the Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, and the Gram-negative Escherichia coli, and all compounds lacked antifungal activity. In addition, compounds 5a, 5b, 5c, 7f and 7 L displayed marked anti-proliferative activity particularly against HepG-2 and MCF-7 cancer cell lines (IC50 < 25 µM). The structures of compounds 5c, 7a and 7f were confirmed by single-crystal X-ray diffraction studies. Compound 5c crystallized…
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Taxonomy
TopicsEicosanoids and Hypertension Pharmacology · Pharmacological Receptor Mechanisms and Effects · Synthesis and biological activity