Preparation, Characterization, and Antioxidant Features of Some New Schiff Bases Derived from Isatins and Hydrazine

Year 2020, Volume: 10 Issue: 1, 439 - 447, 01.03.2020

Halit Muğlu , Hasan Yakan

https://doi.org/10.21597/jist.589004

Cited By: 4

Abstract

New isatins based on Schiff bases were prepared from hydrazine, 5-substituted isatins, and aldehydes under reflux in ethanol. The structures of the synthesized compounds were elucidated by using IR, 13C NMR, 1H NMR spectroscopy and elemental analysis. All the compounds were tested in vitro antioxidant activity with free radical scavenging method using by 1,1-diphenyl-2-picryl hydrazyl (DPPH). The results were given with calculated IC50 values.

Keywords

Schiff bases, isatin, antioxidant features, spectroscopic method, DPPH

Hidrazin ve Isatinlerden Elde Edilen Bazı Yeni Schiff Bazlarının Sentezi, Karakterizasyonu ve Antioksidan Özellikleri

Abstract

Yeni schiff bazlı isatinler, hidrazin, 5-sübstitütentli isatinler ve çeşitli aldehitlerin etil alkolde geri soğutucu altındaki tepkimesi sonucu elde edilmiştir. Sentezlenen bileşiklerin yapısı IR, 13C NMR, 1H NMR spektroskopik veriler ve elementel analiz sonuçlar ile aydınlatılmıştır. Sentezlenen bileşiklerin antioksidan aktivite testleri 2,2-difenil-1-pikril hidrazil (DPPH) radikal giderme yöntemi ile yapılmıştır. Sonuçlar, hesaplanan IC50 (yarı maksimum inhibitör derişim) değerleri ile verilmiştir.

Keywords

Schiff baz, isatin, antioxidant özellikler, spektoskopik yöntem, DPPH

References

• Abbas SY, Farag AA, Ammar YA, Atrees AA, Mohamed AF, El-Henawy AA, 2013. Synthesis, characterization, and antiviral activity of novel fluorinated isatin derivatives. Monatshefte für Chemie-Chemical Monthly, 144: 1725-1733.
• Aboul-Fadl T, Bin-Jubair FA, 2010. Anti-tubercular activity of isatin derivatives. International Journal of Research in Pharmaceutical Sciences, 1: 113-126.
• Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Cremonini MA, Placucci G, 2010. New isatin derivatives with antioxidant activity. European Journal of Medicinal Chemistry, 45: 1374-1378.
• Bakır T, Sayiner HS, Kandemirli F, 2018. Experimental and theoretical investigation of antioxidant activity and capacity of thiosemicarbazones based on isatin derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 193: 493-499.
• Bal TR, Anand B, Yogeeswari P, Sriram D, 2005. Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives. Bioorganic & Medicinal Chemistry Letters, 15: 4451-4455.
• Bekircan O, Bektas H, 2008. Synthesis of Schiff and Mannich bases of isatin derivatives with 4-amino-4, 5-dihydro-1H-1,2,4-triazole-5-ones. Molecules, 13: 2126-2135.
• Blois MS, 1958. Antioxidant determinations by the use of a stable free radical. Nature, 181(4617): 1199.
• Brewer M, 2011. Natural antioxidants: sources, compounds, mechanisms of action, and potential applications. Comprehensive Reviews in Food Science and Food Safety, 10(4): 221-247.
• Chohan ZH, Pervez H, Rauf A, Khan KM, Supuran CT, 2004. Isatin-derived antibacterial and antifungal compounds and their transition metal complexes. Journal of Enzyme Inhibition and Medicinal Chemistry, 19: 417-423.
• Fleming I, Williams DH, 1966. Spectroscopic methods in organic chemistry: McGraw-hill New York.
• Frankel EN, Meyer AS, 2000. The problems of using one‐dimensional methods to evaluate multifunctional food and biological antioxidants. Journal of the Science of Food and Agriculture, 80(13): 1925-1941.
• Gabr MT, El-Gohary NS, El-Bendary ER, El-Kerdawy MM, Ni N, 2017. Isatin-β-thiocarbohydrazones: Microwave-assisted synthesis, antitumor activity and structure-activity relationship. European Journal of Medicinal Chemistry, 128: 36-44.
• Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel J, 2007. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Molecules, 12: 1720-1730.
• Kiran G, Maneshwar T, Rajeshwar Y, Sarangapani M, 2012. Microwave-assisted synthesis, characterization, antimicrobial and antioxidant activity of some new isatin derivatives. Journal of Chemistry 2013.
• Kiran G, Sarangapani M, Gouthami T, Narsimha reddy AR, 2013. Synthesis, characterization, and antimicrobial and antioxidant activities of novel bis-isatin carbohydrazone derivatives. Toxicological & Environmental Chemistry, 95: 367-378.
• Liang C, Xia J, Lei D, Li X, Yao Q, Gao J, 2014. Synthesis, in vitro and in vivo antitumor activity of symmetrical bis-Schiff base derivatives of isatin. European Journal of Medicinal Chemistry, 74: 742-750.
• Manjula P, Sarojini B, Raj CD, 2015. Antibacterial and in vitro antioxidant activities of some 4-amino-1,2,4-triazole-5 (4H)-thione derivatives. Journal of Fundamental and Applied Sciences, 7(3): 394-407.
• Meral R, Doğan, İ, 2012. Karadut (Morus nigra) Katkılı Ekmeğin Antioksidan Aktivitesi ve Fenolik Kompozisyonu. Journal of the Institute of Science and Technology, 2(4): 43-48.
• Naik N, Vijay Kumar H, Vidyashree PB, 2011. Synthesis and evaluation of antioxidant potential of novel isatin analogues. Journal of Pharmacy Research, 4: 2686-2689.
• Özkınalı S, Gür M, Şener N, Alkın S, Çavuş M.S, 2018. Synthesis of new azo schiff bases of pyrazole derivatives and their spectroscopic and theoretical investigations. Journal of Molecular Structure, 1174: 74-83.
• Pandeya SN, Sriram D, Nath G, De Clercq E, 2000. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole. Arzneimittelforschung, 50: 55-59.
• Premanathan M, Radhakrishnan S, Kulangiappar K, Singaravelu G, Thirumalaiarasu V, Sivakumar T, Kathiresan K, 2012. Antioxidant & anticancer activities of isatin (1H-indole-2, 3-dione), isolated from the flowers of Couroupita guianensis Aubl. Indian Journal of Medical Research, 136(5): 822–826.
• Shahidi F, 2015. Antioxidants: Principles and applications. Handbook of antioxidants for food preservation: Woodhead Publishing, 1-14.
• Sinha D, Tiwari AK, Singh S, Shukla G, Mishra P, Chandra H, Mishra AK, 2008. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. European Journal of Medicinal Chemistry, 43: 160-165.
• Sridhar SK, Pandeya SN, Stables JP, Ramesh A, 2002. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. European Journal of Pharmaceutical Sciences, 16: 129-132.
• Uruk T, Kahraman S, 2017. Yaban Mersini (Vaccinium myrtillus) Şarabının Antioksidan Aktivitesinin Araştırılması. Journal of the Institute of Science and Technology, 7(4): 77-83.
• Verma M, Pandeya SN, Singh KN, Stables JP, 2004. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica, 54: 49-56.
• Wanasundara P, Shahidi F, 2005. Antioxidants: Science, technology, and applications. Bailey's industrial oil and fat products.