Synthesis and evaluation of biological activity of 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones

Abstract

To accomplish the synthesis and screening of anticancer and antimicrobial activities of 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones 2-10. Methods. The in vitro anticancer activity of compounds 4, 6, 8-10 has been established by DTP(Developmental Therapeutics Program) of the National Cancer Institute. The antibacterial and antifungal activities of synthesized thiazole-based derivatives were evaluated in vitro with the agar diffusion and broth microdilution methods to wards Gram-positive, Gram-negative bacteria and yeasts. For the synthesized compounds, the in silico drug-likeness screening using SwissADME online server is reported. Results. The novel 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones were synthesized from 1-[2-amino-4-methylthiazol-5-yl]ethanones and various aromatic aldehydes in the Claisen-Schmidt condensation. The synthesized compound 9 was moderately active against the leukemia CCRF-CEM and HL-60(TB), renal cancer UO-31 and breast cancer MCF7 cell lines. The antimicrobial screening led to identification of the active compound 10 against Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans. Conclusions. The results obtained herein provide a platform for structure-based optimization of these newly identified thiazole-based compounds for the anticancer and antibacterial drug design.

Development of Novel Pyridine-Thiazole Hybrid Molecules as Potential Anticancer Agents

“…At the next stage, the ( E )-3-(2-fluorophenyl)-1-[4-methyl-2-(2-pyridylamino)-thiazol-5-yl]-2-propen-1-one ( 3 ) was synthesized from 2 and 2-fluorobenzaldehyde via the Claisen-Schmidt condensation. It is worth noting that for the mentioned reaction, the application of potassium tert -butylate as a catalyst in the ethanol medium led to a higher product yield and purity level, in comparison with using of potassium hydroxide (ethanol medium), as a catalyst [ 28 ]. The following synthetic design was based on the transformations of “enone” fragment of compound 3 .…”