Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity

Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity Publisher

Tuylu Kucukkilinc T¹ ; Safari Yanghagh K² ; Ayazgok B¹ ; Ali Roknipour M² ; Homayouni Moghadam F³ ; Moradi A⁴ ; Emami S⁵ ; Amini M⁶ ; Irannejad H⁵

Show Affiliations

1. Department of Biochemistry, Faculty of Pharmacy, Hacettepe University, Sihhiye, Ankara, 06100, Turkey
2. Student Research Committee, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran
3. Department of Cellular Biotechnology at Cell Science Research Center, Royan Institute for Biotechnology, ACECR, Isfahan, Iran
4. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shahid Sadoughi Yazd University of Medical Sciences, Yazd, Iran
5. Department of Medicinal Chemistry, Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran
6. Department of Medicinal Chemistry, Drug Design & Development Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Medicinal Chemistry Research Published:2017

Abstract

A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a–f, 8a–d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and β-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 µM in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in β-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells. © 2017, Springer Science+Business Media, LLC.

2. Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease, Frontiers in Chemistry (2022)

3. Structure-Based Design, Synthesis, Molecular Docking Study and Biological Evaluation of 1,2,4-Triazine Derivatives Acting As Cox/15-Lox Inhibitors With Anti-Oxidant Activities, Journal of Enzyme Inhibition and Medicinal Chemistry (2016)

4. New Racemic Annulated Pyrazolo[1,2-B]Phthalazines As Tacrine-Like Ache Inhibitors With Potential Use in Alzheimer's Disease, European Journal of Medicinal Chemistry (2017)

5. Beyond the 5-Ht3 Receptors: A Role for Α7nach Receptors in Neuroprotective Aspects of Tropisetron, Human and Experimental Toxicology (2015)

6. Anticonvulsant Activity of 1,2,4-Triazine Derivatives With Pyridyl Side Chain: Synthesis, Biological, and Computational Study, Medicinal Chemistry Research (2015)

7. Chromone Derivatives Bearing Pyridinium Moiety As Multi-Target-Directed Ligands Against Alzheimer's Disease, Bioorganic Chemistry (2021)

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Style	Citing Format
MLA	Tuylu Kucukkilinc T, et al.. "Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity." Medicinal Chemistry Research, vol. 26, no. 11, 2017, pp. 3057-3071.
APA	Tuylu Kucukkilinc T, Safari Yanghagh K, Ayazgok B, Ali Roknipour M, Homayouni Moghadam F, Moradi A, Emami S, Amini M, Irannejad H (2017). Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity. Medicinal Chemistry Research, 26(11), 3057-3071.
Chicago	Tuylu Kucukkilinc T, Safari Yanghagh K, Ayazgok B, Ali Roknipour M, Homayouni Moghadam F, Moradi A, Emami S, Amini M, Irannejad H. "Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity." Medicinal Chemistry Research 26, no. 11 (2017): 3057-3071.
Harvard	Tuylu Kucukkilinc T et al. (2017) 'Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity', Medicinal Chemistry Research, 26(11), pp. 3057-3071.
Vancouver	Tuylu Kucukkilinc T, Safari Yanghagh K, Ayazgok B, Ali Roknipour M, Homayouni Moghadam F, Moradi A, et al.. Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity. Medicinal Chemistry Research. 2017;26(11):3057-3071.
BibTex	@article{ author = {Tuylu Kucukkilinc T and Safari Yanghagh K and Ayazgok B and Ali Roknipour M and Homayouni Moghadam F and Moradi A and Emami S and Amini M and Irannejad H}, title = {Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity}, journal = {Medicinal Chemistry Research}, volume = {26}, number = {11}, pages = {3057-3071}, year = {2017} }
RIS	TY - JOUR AU - Tuylu Kucukkilinc T AU - Safari Yanghagh K AU - Ayazgok B AU - Ali Roknipour M AU - Homayouni Moghadam F AU - Moradi A AU - Emami S AU - Amini M AU - Irannejad H TI - Synthesis and Neuroprotective Activity of Novel 1,2,4-Triazine Derivatives With Ethyl Acetate Moiety Against H2o2 and Aβ-Induced Neurotoxicity JO - Medicinal Chemistry Research VL - 26 IS - 11 SP - 3057 EP - 3071 PY - 2017 ER -

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