Abstract
BackgroundThe synthesis of new thiazole derivatives is very important because of their diverse biological activities. Also , many drugs containing thiazole ring in their skeletons are available in the market such as Abafungin, Acotiamide, Alagebrium, Amiphenazole, Brecanavir, Carumonam, Cefepime, and Cefmatilen.ResultsEthyl cyanoacetate reacted with phenylisothiocyanate, chloroacetone, in two different basic mediums to afford the thiazole derivative 6, which reacted with dimethylformamide- dimethyl acetal in the presence of DMF to afford the unexpected thiazole derivative 11. The structures of the thiazoles 6 and 11 were optimized using B3LYP/6-31G(d,p) method. The experimentally and theoretically geometric parameters agreed very well. Also, the natural charges at the different atomic sites were predicted. HOMO and LUMO demands were discussed. The anticancer activity of the prepared compounds was evaluated and showed moderate activity.ConclusionsSynthesis of novel thiazole derivatives was done. The structure was established using X-ray and spectral analysis. Optimized molecular structures at the B3LYP/6-31G(d,p) level were investigated. Thiazole derivative 11 has more electropositive S-atom than thiazole 6. The HOMO–LUMO energy gap is lower in the former compared to the latter. The synthesized compounds showed moderate anticancer activity.
Highlights
Marketed anticancer medications have increasing problems of various toxic side effects and development of resistance to their action
Its structure was established from X-ray analysis (Fig. 1) [24] and was confirmed using elemental and spectral analysis (IR, 1H NMR, 13C NMR)
The suggested mechanism for the synthesis of thiazole 6 is outlined in Scheme 1
Summary
Marketed anticancer medications have increasing problems of various toxic side effects and development of resistance to their action. There is an urgent clinical need for the synthesis of novel anticancer agents that are potentially more effective and have higher safety profile. The synthesis of different thiazole derivatives has attracted great attention due to their diverse biological activities that include anticonvulsant [1, 2], antimicrobial [3, 4], anti-inflammatory [5, 6], anticancer [7], antidiabetic [8], anti-HIV [9], anti-Alzheimer [10], antihypertensive [11], and antioxidant activities [12]. In continuation of our interest in the synthesis of new biologically active heterocyclic rings [16–22] and motivated by these information, it was thought worthwhile to synthesize some novel thiazole derivatives and to test their antitumor activity in order to discover new potentially biologically active drugs of synthetic origin. The synthesis of new thiazole derivatives is very important because of their diverse biological activities. Many drugs containing thiazole ring in their skeletons are available in the market such as Abafungin, Acotia‐ mide, Alagebrium, Amiphenazole, Brecanavir, Carumonam, Cefepime, and Cefmatilen
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
