Halit MUĞLU, Hasan YAKAN, Temel Kan BAKIR

Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde

New bis(isatins-thio/carbohydrazones) based on Schiff bases were prepared from terephthalaldehyde biscarbohydrazone and 5-substituted isatins in the presence of a drop of sulfuric acid under reflux in ethanol. Terephthalaldehyde bis(thio/carbohydrazone) was synthesized by the reaction of (thio)/carbohydrazide and terephthalaldehyde in the presence of a few drops of acetic acid under reflux in ethanol. The structures of these synthesized compounds were determined using IR, 1H NMR, and 13C NMR spectroscopy and elemental analysis. The in vitro antioxidant activity of all the compounds was determined by the 1,1-diphenyl-2-picryl hydrazyl (DPPH.) free radical scavenging method. Compound 2 showed the best antioxidant activity.

Keywords:

vIsatin, carbohydrazone Schiff bases, DPPH, spectroscopic techniques,

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1. Sridhar SK, Pandeya SN, Stables JP, Ramesh A. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. European Journal of Pharmaceutical Sciences 2002; 16: 129-132.
2. Verma M, Pandeya SN, Singh KN, Stables JP. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica 2004; 54: 49-56.
3. Pandeya S, Sriram D, Nath G, DeClercq E. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl) thiazol-2-yl] thiosemicarbazide. European Journal of Pharmaceutical Sciences 1999; 9: 25-31.
4. Sriram D, Pandeya S, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole. Arzneimittelforschung 2000; 50: 55-59.
5. Sridhar SK, Saravanan M, Ramesh A. Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives. European Journal of Medicinal Chemistry 2001; 36: 615-625.
6. Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel J. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Molecules 2007; 12: 1720-1730.
7. Jarrahpour A, Sheikh J, El Mounsi I, Juneja H, Hadda TB. Computational evaluation and experimental in vitro antibacterial, antifungal and antiviral activity of bis-Schiff bases of isatin and its derivatives. Medicinal Chemistry Research 2013; 22: 1203-1211.
8. El-Sawaf AK, El-Essawy F, Nassar AA, El-Samanody E-SA. Synthesis, spectral, thermal and antimicrobial studies on cobalt (II), nickel (II), copper (II), zinc (II) and palladium (II) complexes containing thiosemicarbazone ligand. Journal of Molecular Structure 2018; 1157: 381-394.
9. Akocak S, Lolak N, Tuneg M, Boga M. Antioxidant, acetylcholinesterase and butyrylcholinesterase inhibition profiles of histamine Schiff bases. Journal of the Turkish Chemical Society Section A 6: 157-164.
10. Kiran G, Sarangapani M, Gouthami T, Narsimha Reddy AR. Synthesis, characterization, and antimicrobial and antioxidant activities of novel bis-isatin carbohydrazone derivatives. Toxicological & Environmental Chemistry 2013; 95: 367-378.
11. Muğlu H, Çavuş MS, Bakır T, Yakan H. Synthesis, characterization, quantum chemical calculations and antioxidant activity of new bis-isatin carbohydrazone and thiocarbohydrazone derivatives. Journal of Molecular Structure 2019; 1196: 819-827.
12. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one. Pharmaceutica Acta Helvetiae 1999; 74: 11-17.
13. Gangarapu K, Manda S, Jallapally A, Thota S, Karki SS et al. Synthesis of thiocarbohydrazide and carbohydrazide derivatives as possible biologically active agents. Medicinal Chemistry Research 2014; 23: 1046-1056.
14. Akgül Ö, Tarikoğullari AH, Köse FA, Kirmizibayrak PB, Pabuççuoğlu MV. Synthesis and cytotoxic activity of some 2-(2,3-dioxo-2,3-dihydro-1H -indol-1-yl)acetamide derivatives. Turkish Journal of Chemistry 2013; 37: 204-212.
15. Chohan ZH, Pervez H, Rauf A, Khan KM, Supuran CT. Isatin-derived antibacterial and antifungal compounds and their transition metal complexes. Journal of Enzyme Inhibition and Medicinal Chemistry 2004; 19: 417-423.
16. Abbas SY, Farag AA, Ammar YA, Atrees AA, Mohamed AF et al. Synthesis, characterization, and antiviral activity of novel fluorinated isatin derivatives. Monatshefte für Chemie-Chemical Monthly 2013; 144: 1725-1733.
17. Bakır T, Sayiner HS, Kandemirli F. Experimental and theoretical investigation of antioxidant activity and capacity of thiosemicarbazones based on isatin derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 2018; 193: 493-499.
18. Haribabu J, Subhashree G, Saranya S, Gomathi K, Karvembu R et al. Isatin based thiosemicarbazone derivatives as potential bioactive agents: anti-oxidant and molecular docking studies. Journal of Molecular Structure 2016; 1110: 185-195.
19. Pandeya SN, Raja AS, Stables JP. Synthesis of isatin semicarbazones as novel anticonvulsants-role of hydrogen bonding. Journal of Pharmacy and Pharmaceutical Sciences 2002; 5: 266-271.
20. Aboul-Fadl T, Bin-Jubair FA. Anti-tubercular activity of isatin derivatives. International Journal of Research in Pharmaceutical Sciences 2010; 1: 113-126.
21. Sriram D, Yogeeswari P, Meena K. Synthesis, anti-HIV and antitubercular activities of isatin derivatives. Die Pharmazie-An International Journal of Pharmaceutical Sciences 2006; 61: 274-277.
22. Aboul-Fadl T, Bin-Jubair FA. Anti-tubercular activity of isatin derivatives. International Journal of Research in Pharmaceutical Sciences 2010; 1: 123-126.
23. Bal TR, Anand B, Yogeeswari P, Sriram D. Synthesis and evaluation of anti-HIV activity of isatin β -thiosemicarbazone derivatives. Bioorganic & Medicinal Chemistry Letters 2005; 15: 4451-4455.
24. Robak J, Marcinkiewicz E. Scavenging of reactive oxygen species as the mechanism of drug action. Polish Journal Pharmacology 1995; 47 (2): 89-98.
25. Krumova K, Cosa G. Overview of reactive oxygen species. In: Nonell S, Flors C (editors). Singlet Oxygen: Applications in Biosciences and Nanosciences. London, UK: Royal Society of Chemistry, 2016, pp. 1-21.
26. Günsel A, AlıcıEH, Bilgicli AT, ArabacıG, Yaraşır MN. Antioxidant properties of water-soluble phthalocyanines containing quinoline 5-sulfonic acid groups. Turkish Journal of Chemistry 2019; 43: 1030-1039.
27. Sindhi V, Gupta V, Sharma K, Bhatnagar S, Kumari R et al. Potential applications of antioxidants–A review. Journal of Pharmacy Research 2013; 7: 828-835.
28. Yaşa H. Synthesis, characterization, and evaluation of antioxidant activity of new γ -and δ -imino esters. Turkish Journal of Chemistry 2018; 42: 1105-1112.
29. Blois MS. Antioxidant determinations by the use of a stable free radical. Nature 1958; 181: 1199.
30. Naik N, Vijay Kumar H, Vidyashree PB. Synthesis and evaluation of antioxidant potential of novel isatin analogues. Journal of Pharmacy Research 2011; 4: 2686-2689.
31. Frankel EN, Meyer AS. The problems of using one-dimensional methods to evaluate multifunctional food and biological antioxidants. Journal of the Science of Food and Agriculture 2000; 80: 1925-1941.
32. Bekircan O, Bektas H. Synthesis of Schiff and Mannich bases of isatin derivatives with 4-amino-4, 5-dihydro-1H -1, 2, 4-triazole-5-ones. Molecules 2008; 13: 2126-2135.
33. Chinnasamy RP, Sundararajan R, Govindaraj S. Synthesis, characterization, and analgesic activity of novel Schiff base of isatin derivatives. Journal of Advanced Pharmaceutical Technology & Research 2010; 1: 342-347.
34. Özkınalı S, Gür M, Şener N, Alkın S, Çavuş MS. Synthesis of new azo Schiff bases of pyrazole derivatives and their spectroscopic and theoretical investigations. Journal of Molecular Structure 2018; 1174: 74-83.
35. Williams D, Fleming I. RNA Structure and NMR Spectroscopy. Spectroscopic Methods in Organic Chemistry. New York, NY, USA: McGraw-Hill, 1996.
36. Pretsch E, Buehlmann P, Affolter C, Pretsch E, Bhuhlmann P et al. Structure Determination of Organic Compounds. Berlin, Germany: Springer, 2000.
37. Kemp W. Organic Spectroscopy. New York, NY, USA: Macmillan International Higher Education, 2017.
38. Brewer M. Natural antioxidants: sources, compounds, mechanisms of action, and potential applications. Comprehensive Reviews in Food Science and Food Safety 2011; 10: 221-247.
39. Shahidi F. Handbook of Antioxidants for Food Preservation. Amsterdam, the Netherlands: Elsevier, 2015, pp. 1-14.
40. Pakravan P, Kashanian S, Khodaei MM, Harding FJ. Biochemical and pharmacological characterization of isatin and its derivatives: from structure to activity. Pharmacological Reports 2013; 65: 313-335.
41. Kiran G, Maneshwar T, Rajeshwar Y, Sarangapani M. Microwave-assisted synthesis, characterization, antimicrobial and antioxidant activity of some new isatin derivatives. Journal of Chemistry 2013; 2013: 192039.
42. Gudipati R, Narsimha R, Anreddy R, Manda S. Synthesis, anticancer and antioxidant activities of some novel N -(benzo[d]oxazol-2-yl)-2-(7- or 5-substituted-2-oxoindolin-3-ylidene) hydrazinecarboxamide derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 2011; 26: 813-818.