Synthesis of Phenyl-1,3,4-Thiadiazol-2-Amine Derivatives with in-Vitro Antioxidant Activity
Keywords:
1,3,4-Thiadiazol thiosemicarbazide, 4- hydroxy coumarin, DPPHAbstract
In this research, the synthesis of structurally important antioxidants 7-Hydroxy-4-Methyl Coumarin (C1) and 4- Hydroxy Coumarin derivatives was conducted. Coumarin was modified by various reaction steps for the production of target compounds. Different spectroscopic techniques characterized molecular structures FT-IR ,NMR. Antioxidant activity was carried out against 1,1-diphenyl-2-picrylhydrazyl (DPPH) in vitro spectrophometric assays. Compared to ascorbic acid, all compounds exhibited high antioxidant efficiency. Among compounds, Compound 9 performance was considered to be the highest (92%), followed by compounds 8 and 10 (90%). Ascorbic acid has been used as a standard drug with inhibition of the percentage 90.5%.
References
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[20] Najeebullah, K.; Samiullah, N.; Attiq-ur-Rehman, K.; Rasool, B. T.; Nazi, M.; Syed-Waheed, A. S.; Irshad, A.; Muhammad, A.; Abdul-Baqi, A.; "Determination of Antioxidants and Antimicrobial Activities of Platytaenia multicaule"; Al-Nahrain J. Sci. 22(4), 19–29, 2019.
[21] Ghufran, S. N.; Amer, H. A.; Najwa, S. A.; Wafaa, R. A.; “Evaluation of Estridiol and Some Antioxidant in Breast Cancer Iraqi Women"; Al-Nahrain J. Sci. 21(1), 35–40, 2018.
[22] Ghufran, S. N.; Amer, H. A.; Najwa, S. A.; Wafaa, R. A.; “Evaluation of Estridiol and Some Antioxidant in Breast Cancer Iraqi Women"; Al-Nahrain J. Sci. 21(1), 35–40, 2018.
[23] Hameed, S.; Ibraheem, H.; “Synthesis, Characterization and Biological Activity of Some Heterocyclic Compounds Containing Quinoline Molecule"; Al-Nahrain J. Sci. 23(1), 1–6, 2020.
[2] Al-Amiery, A. A.; Al-Majedy, K. Y.; Ibrahim, H. H.; Al-Tamimi, A. A.; "Antioxidant, Antimicrobial and Theoretical Studies of the Thiosemicarbazone Derivative Schiff Base 2-(2-Imino-1- Methyl-Imidazolidin-4 Ylidene) Hydrazine-Carbo-Thioamide (IMHC)". Org. Med. Chem. Lett. 2(4),1–7, 2012.
[3] Cacic, M.; Molnar M.; "Design, Synthesis and Characterization of Some Novel 3-Coumarinyl-5 Aryliden-1,3-Thiazolidine-2,4-Diones and their Antioxidant Activity"; Z. Naturforsch 66(b), 177– 183, 2011.
[4] Foti, M.; Piattelli, M.; Baratta, M. T.; Ruberto, G.; "Flavonoids, Coumarins, Antioxidants in a Micellar System, Structure-Activity and Cinnamic Acids as Relationship"; J. Agric. Food Chem. 44, 497–501, 1996.
[5] Fylaktakidou, K. C.; Hadjipavlou-Litina, D. J.; Litinas, K. E.; Nikolaides, D. N.; "Natural and Synthetic Coumarin Derivatives with Anti-Inflammatory / Antioxidant Activities"; Curr. Pharm. Des. 10, 3813-3833,2004.
[6] Bailly, F.; Maurin, C.; Teissier, E.; Vezina, H.; Cotelle, P.; " Antioxidant Properties of 3-Hydroxycoumarin Derivatives"; Bioorg. Med. Chem. 12, 5611–5618,2004.
[7] Anand P.; Singh B.; Singh N. A.; "Review on Coumarins as Acetylcholinesterase Inhibitors for Alzheimer’s Disease"; Bioorg Med Chem. 20(3):1175-80,2012.
[8] Al-Majedy, Y. K.; Al-Duhaidahawi, D. L.; Al-Azawi, K. F.; Kadhum, A. A. H.; Al-Amiery, A. A.; Mohamad, A. B.; "Coumarins as Potential Antioxidant Agents Complemented with Suggested Mechanisms and Approved by Molecular Modeling Studies"; Molecules 21(2), 1–11, 2016.
[9] Liaras, K.; Geronikaki, A.; Glamoc, l. J.; Ciric, A., Sokovic, M.; "Thiazole-Based Chalcones as Potent Antimicrobial Agents.Synthesis and Biological Evaluation"; Bioorg. Med. Chem. 19, 3135–3140, 2011.
[10] Vicini, P.; Geronikaki, A.; Anastasia, K.; Incertia, M.; Zani, F.; "Synthesis and Antimicrobial Activity of Novel 2-Thiazolylimino-5- Arylidene-4-Thiazolidinones"; Bioorg. Med. Chem. 14, 3859–3864, 2006.
[11] Sies, H.; "Oxidative Stress: Oxidants and Antioxidants"; Exp. Physiol. 82(2), 291–295, 1997.
[12] Abdalla, A. E.; Roozen, J. P.; "Effect of Plant Extracts on the Oxidative Stability of Sunflower Oil and Emulsion"; Food Chem. 64, 323–329, 1999.
[13] Mishra, P.; Jatav, V.; Kashaw, S. K.; "Some Novel 2-Methyl-3-(1′3′4′-Thiadiazolyl)-4-(3H) Quinazolinones with Anticonvulsant and CNS Depressant Activity"; J. Indian Chem. Soc. 83, 1165–1170, 2006.
[14] Abdou, O. A.; Sobhi, M. G ;Nadia, A. A.; Saher, M. K.; " Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents"; J. Molec. 21, 929–935, 2016.
[15] Al-Amiery, A.; Al-Majedy, A.; Al-Duhaidahawi, D.; Kadhum, A. A.; Mohamad, A. B.; "Green Antioxidants: Synthesis and Scavenging Activity of Coumarin-Thiadiazoles as Potential Antioxidants Complemented by Molecular Modeling Studies"; Free Rad. Antioxid. 6(2), 173–177, 2016.
[16] Al-Amiery, A. A.; Al-Majedy, Y. K.; Kadhum, A. A. H.; Mohamad, A. B.; “Hydrogen Peroxide Scavenging Activity of Novel Coumarins Synthesized Using Different Approaches”, PLoS ONE 10(7), e0132175, 1-9 2015.
[17] Al-Amiery, A. A.; Al-Majedy, Y. K.; Kadhum, A. A. H.; Mohamad, A. B.; "Novel macromolecules derived from coumarin: synthesis and antioxidant activity"; Sci. Rep. 5, 11825, 2015.
[18] Xue. H.; Lu, X.; Zheng, P.; Liu, L.; Han, C.; Hu, J.; Liu, Z.; Ma, T.; Li, Y.; Wang, L.; Chen, Z.; Liu, G.; "Highly Supperssing Wild-Type HIV-1 and Y181C Mutant HIV-1 Strains by 10-Chloromethyl-11demethyl-12 oxocalanolide A with Druggable Profile"; J. Med. Chem. 53(3), 1397–1401, 2010.
[19] Roussaki, M.; Kontogiorgis, C. A.; Hadjipavlou-Litina, D.; Hamilakis, S.; Detsi, A.; "A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity"; Bioorg. Med. Chem. Lett. 20, 3889–3892, 2010.
[20] Najeebullah, K.; Samiullah, N.; Attiq-ur-Rehman, K.; Rasool, B. T.; Nazi, M.; Syed-Waheed, A. S.; Irshad, A.; Muhammad, A.; Abdul-Baqi, A.; "Determination of Antioxidants and Antimicrobial Activities of Platytaenia multicaule"; Al-Nahrain J. Sci. 22(4), 19–29, 2019.
[21] Ghufran, S. N.; Amer, H. A.; Najwa, S. A.; Wafaa, R. A.; “Evaluation of Estridiol and Some Antioxidant in Breast Cancer Iraqi Women"; Al-Nahrain J. Sci. 21(1), 35–40, 2018.
[22] Ghufran, S. N.; Amer, H. A.; Najwa, S. A.; Wafaa, R. A.; “Evaluation of Estridiol and Some Antioxidant in Breast Cancer Iraqi Women"; Al-Nahrain J. Sci. 21(1), 35–40, 2018.
[23] Hameed, S.; Ibraheem, H.; “Synthesis, Characterization and Biological Activity of Some Heterocyclic Compounds Containing Quinoline Molecule"; Al-Nahrain J. Sci. 23(1), 1–6, 2020.
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2020-06-04
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Synthesis of Phenyl-1,3,4-Thiadiazol-2-Amine Derivatives With in-Vitro Antioxidant Activity. ANJS 2020, 23 (2), 33-38.
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