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

YAKAN, HASAN; Muğlu, Halit; Bakır, Temel Kan

doi:10.3906/kim-1910-13

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

Halit MUĞLU, (Kastamonu Üniversitesi)

Hasan YAKAN, (Ondokuz Mayıs Üniversitesi)

Temel Kan BAKIR (Kastamonu Üniversitesi)

Turkish Journal of Chemistry

7 0

Yıl: 2020 Cilt: 44 Sayı: 1 Sayfa Aralığı: 237 - 248 Metin Dili: İngilizce DOI: 10.3906/kim-1910-13 İndeks Tarihi: 04-05-2020

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

Öz:

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 inthe presence of a few drops of acetic acid under reflux in ethanol. The structures of these synthesized compounds weredetermined using IR, 1 H NMR, and 13 C NMR spectroscopy and elemental analysis. The in vitro antioxidant activityof 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.

Anahtar Kelime:

Konular: Kimya, Analitik Kimya, Uygulamalı Kimya, Organik Kimya, Tıbbi Mühendislik, Kimya Kimya, İnorganik ve Nükleer

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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.

APA	Muğlu H, YAKAN H, Bakır T (2020). Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. , 237 - 248. 10.3906/kim-1910-13
Chicago	Muğlu Halit,YAKAN HASAN,Bakır Temel Kan Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. (2020): 237 - 248. 10.3906/kim-1910-13
MLA	Muğlu Halit,YAKAN HASAN,Bakır Temel Kan Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. , 2020, ss.237 - 248. 10.3906/kim-1910-13
AMA	Muğlu H,YAKAN H,Bakır T Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. . 2020; 237 - 248. 10.3906/kim-1910-13
Vancouver	Muğlu H,YAKAN H,Bakır T Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. . 2020; 237 - 248. 10.3906/kim-1910-13
IEEE	Muğlu H,YAKAN H,Bakır T "Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde." , ss.237 - 248, 2020. 10.3906/kim-1910-13
ISNAD	Muğlu, Halit vd. "Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde". (2020), 237-248. https://doi.org/10.3906/kim-1910-13

APA	Muğlu H, YAKAN H, Bakır T (2020). Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. Turkish Journal of Chemistry, 44(1), 237 - 248. 10.3906/kim-1910-13
Chicago	Muğlu Halit,YAKAN HASAN,Bakır Temel Kan Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. Turkish Journal of Chemistry 44, no.1 (2020): 237 - 248. 10.3906/kim-1910-13
MLA	Muğlu Halit,YAKAN HASAN,Bakır Temel Kan Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. Turkish Journal of Chemistry, vol.44, no.1, 2020, ss.237 - 248. 10.3906/kim-1910-13
AMA	Muğlu H,YAKAN H,Bakır T Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. Turkish Journal of Chemistry. 2020; 44(1): 237 - 248. 10.3906/kim-1910-13
Vancouver	Muğlu H,YAKAN H,Bakır T Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. Turkish Journal of Chemistry. 2020; 44(1): 237 - 248. 10.3906/kim-1910-13
IEEE	Muğlu H,YAKAN H,Bakır T "Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde." Turkish Journal of Chemistry, 44, ss.237 - 248, 2020. 10.3906/kim-1910-13
ISNAD	Muğlu, Halit vd. "Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde". Turkish Journal of Chemistry 44/1 (2020), 237-248. https://doi.org/10.3906/kim-1910-13