Research Article
Design, Synthesis and Evaluation of Pyrrol-thiazole Derivatives as AChE and BuChE Inhibitory and Antioxidant Activities
Abstract
Thiazole rings are one of the most frequently used heterocyclic moieties and are found in a wide variety of biologically active chemicals. In this research project, we report the synthesis and biological activities of some new thiazole derivatives (2a-2c) as potent anti-Alzheimer’s agents. These final compounds’ structures were characterized by spectral (1H NMR, 13C NMR, and MS spectra) analyses. The highest inhibitory activity against AChE was demonstrated by compound 2c (23.73 ± 0.018 %) with chloro substitution at the meta and para positions of the phenyl ring, while the highest inhibitory activity against BuChE was produced by compound 2a (28.87± 0.003 %) with cyano substitution at the f position of the phenyl ring. Ferrous ion-chelating and DPPH techniques were also used to assess the compounds' antioxidant properties. Compound 2a showed antioxidant effect according to the DPPH method with an IC50 value of 27.18 ± 0.009 µM.
Keywords
References
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Year 2023,
Volume: 44 Issue: 4, 625 - 628, 28.12.2023
Abstract
References
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- [3] Mishra D., Fatima A., Kumar P., Munjal N.S., Singh B.K., Singh R., Synthesis of Benzothiazole Linked Triazole Conjugates and Their Evaluation Against Cholinesterase Enzymes, Chem. Select., 7 (2022) e202203060.
- [4] Faghih Z., Khabnadideh S., Sakhteman A., Shirazi A.K., Yari H.A., Chatraei A., Rezaei Z., Sadeghian S., Synthesis, biological evaluation and molecular modeling studies of novel carbazole-benzylpiperazine hybrids as acetylcholinesterase and butyrylcholinesterase inhibitors, J. Mol. Struct., 1272 (2023) 134209.
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- [9] Zhou S., & Huang G., Synthesis and inhibitory activities of inhibitors for the treatment of Alzheimer’s disease, Chem. Biol. Drug Des., 99 (2022) 727-735.
- [10] Silalai P., Jaipea S., Tocharus J., Athipornchai A., Suksamrarn A., & Saeeng R., New 1,2,3-Triazole-genipin Analogues and Their Anti-Alzheimer’s Activity, ACS omega., 7 (2022) 24302-24316.
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- [13] Kilic B., Bardakkaya M., Sagkan R. I., Aksakal F., Shakila S., & Dogruer D.S., New thiourea and benzamide derivatives of 2-aminothiazole as multi-target agents against Alzheimer's disease: Design, synthesis, and biological evaluation, Bioorg. Chem., 131 (2023) 106322.
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- [15] Dinis T.C.P., Madeira V.M.C., Almeida L.M., Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and peroxyl radical scavengers, Arch. Biochem. Biophys., 315 (1994) 161–169.
- [16] Ercetin T., Senol F.S., Orhan I.E. and Toker G., Comparative assessment of antioxidant and cholinesterase inhibitory properties of the marigold extracts from Calendula arvensis L. and Calendula officinalis L, Ind. Crops. Prod., 36 (2012) 203-208.
- [17] Blois M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181 (1958) 1199-1200.
- [18] Işık A., Çevik U.A., Celik I., Erçetin T., Koçak A., Özkay Y., & Kaplancıklı Z.A., Synthesis, characterization, molecular docking, dynamics simulations, and in silico absorption, distribution, metabolism, and excretion (ADME) studies of new thiazolylhydrazone derivatives as butyrylcholinesterase inhibitors, Z. Naturforsch. C., 77 (2022) 447-457.
There are 18 citations in total.
Details
| Primary Language | English |
|---|---|
| Subjects | Pharmacology and Pharmaceutical Sciences |
| Journal Section | Research Article |
| Authors | |
| Submission Date | February 24, 2023 |
| Acceptance Date | November 14, 2023 |
| Publication Date | December 28, 2023 |
| Published in Issue | Year 2023 Volume: 44 Issue: 4 |
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