Login Register Cart 0
Generic placeholder image

Letters in Drug Design & Discovery

Editor-in-Chief

ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

Back
Research Article

Green Synthesis, Characterization, DPPH and Ferrous Ion-chelating (FIC) Activity of Tetrakis-Schiff’s Bases of Terephthalaldehyde

Author(s): Momin Khan*, Umar Ali, Anis Ur Rahman, Muhammad Ibrahim, Abdul Hameed, Muhammad Asif, Zahid Hussain, Kanwal, Khalid Mohammed Khan, Shahnaz Perveen and Munir ur Rehman

Volume 16, Issue 3, 2019

Page: [249 - 255] Pages: 7

DOI: 10.2174/1570180815666180531101404

Price: $65

Abstract

Background: The role of small molecules as antioxidants to prevent the oxidation of other molecules and inhibit them from radical formation is the area of much interest to cure disease especially cancer. Moreover, the antioxidants play important role as stabilizers to prevent oxidation of fuels and lubricants.

Methods: In the present study, fifteen tetrakis-Schiff’s bases derivatives (1-15) were synthesized and screened for their antioxidant activities. Compounds 1-15 were synthesized by continuous stirring of reaction mixture of 1,4-bis (hydrazonomethyl)benzene (1 mmol) with various substituted aromatic aldehydes (2 mmol) in distilled water using acetic acid as catalyst at room temperature for 2-10 min.

Results: Our present study showed that all compounds are better ferrous ion-chelating agents except compound 1,4-bis((E)-((E)-(3,4-dimethoxybenzylidene)hydrazono)methyl)benzene (6) (IC50 = 329.26 ± 4.75 µM) which has slightly low activity than the standard EDTA (IC50 = 318.40 ± 5.53 μM). In addition, DPPH radical scavenging activity of eleven compounds showed higher activity than the standard. However, remaining four compounds showed comparable radical scavenging activity to the standard DPPH (IC50 = 257.77 ± 4.60 µM).

Conclusion: The series of fifteen Schiff’s bases (1-15) were synthesized and evaluated as antioxidants. From both assays, it has been demonstrated that most of the tetrakis-Schiff’s bases have potential to serve as leads for the development of antioxidant agents for future research.

Keywords: Green chemistry, schiff’s bases, DPPH (2, 2-diphenyl-1-picrylhydrazyl), terephthalaldehyde, ferrous ion-chelating, antioxidants.

« Previous Next »
Graphical Abstract

[1]
Schiff, H. Mittheilungen aus dem Universitätslaboratorium in Pisa: eine neue Reihe organischer Basen. Justus Liebigs Ann. Chem., 1864, 131, 118.
[2]
Panneerselvam, P.; Nair, R.R.; Vijayalakshmi, G.; Subramanian, E.H.; Sridhar, S.K. Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents. Eur. J. Med. Chem., 2005, 40, 225.
[3]
Sridhar, S.K.; Saravanan, M.; Ramesh, A. Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur. J. Med. Chem., 2001, 36, 615.
[4]
Bharti, S.K.; Nath, G.; Tilak, R.; Singh, S. Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2, 4-disubstituted thiazole ring. Eur. J. Med. Chem., 2010, 45, 651.
[5]
da Silva, C.M.; da Silva, D.L.; Modolo, L.V.; Alves, R.B.; de Resende, M.A.; Martins, C.V.; de Fátima, Â. Schiff bases: A short review of their antimicrobial activities. J. Adv. Res., 2011, 2, 1.
[6]
Anand, P.; Patil, V.; Sharma, V.; Khosa, R.; Masand, N. Schiff bases. A review on biological insights; Int. J. Drug Discov, 2012, p. 3.
[7]
Kumar, K.S.; Ganguly, S.; Veerasamy, R.; De Clercq, E. Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4 (3) H-ones. Eur. J. Med. Chem., 2010, 45, 5474.
[8]
Sriram, D.; Yogeeswari, P.; Myneedu, N.S.; Saraswat, V. Abacavir prodrugs: Microwave-assisted synthesis and their evaluation of anti-HIV activities. Bioorg. Med. Chem. Lett., 2006, 16, 2127.
[9]
Li, Y-F.; Liu, Z-Q. Ferrocenyl Schiff base as novel antioxidant to protect DNA against the oxidation damage. Eur. J. Pharm. Sci., 2011, 44, 158.
[10]
Neochoritis, C.G.; Zarganes-Tzitzikas, T.; Tsoleridis, C.A.; Stephanidou-Stephanatou, J.; Kontogiorgis, C.A.; Hadjipavlou-Litina, D.J.; Choli-Papadopoulou, T. One-pot microwave assisted synthesis under green chemistry conditions, antioxidant screening, and cytotoxicity assessments of benzimidazole Schiff bases and pyrimido [1, 2-a] benzimidazol-3 (4H)-ones. Eur. J. Med. Chem., 2011, 46, 297.
[11]
Sashidhara, K.V.; Rosaiah, J.N.; Bhatia, G.; Saxena, J. Novel keto-enamine Schiff’s bases from 7-hydroxy-4-methyl-2-oxo-2H-benzo [h] chromene-8, 10-dicarbaldehyde as potential antidyslipidemic and antioxidant agents. Eur. J. Med. Chem., 2008, 43, 2592.
[12]
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. Eur. J. Pharm. Sci., 1999, 9, 25.
[13]
Karthikeyan, M.S.; Prasad, D.J.; Poojary, B.; Bhat, K.S.; Holla, B.S.; Kumari, N.S. Synthesis and biological activity of Schiff and Mannich bases bearing 2, 4-dichloro-5-fluorophenyl moiety. Bioorg. Med. Chem., 2006, 14, 7482.
[14]
Cordes, E.; Jencks, W. The mechanism of hydrolysis of Schiff bases derived from aliphatic amines. J. Am. Chem. Soc., 1963, 85, 2843.
[15]
Rao, V.K.; Reddy, S.S.; Krishna, B.S.; Naidu, K.R.M.; Raju, C.N.; Ghosh, S. Synthesis of Schiff’s bases in aqueous medium: A green alternative approach with effective mass yield and high reaction rates. Green Chem. Lett. Rev., 2010, 3, 217.
[16]
Boozer, C.E.; Hammond, G.S.; Hamilton, C.E.; Sen, J.N. Air Oxidation of Hydrocarbons. 1 II. The Stoichiometry and Fate of Inhibitors in Benzene and Chlorobenzene. J. Am. Chem. Soc., 1955, 77, 3233.
[17]
Balasundram, N.; Sundram, K.; Samman, S. Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chem., 2006, 99, 191.
[18]
Tan, D.X.; Manchester, L.C.; Terron, M.P.; Flores, L.J.; Reiter, R.J. One molecule, many derivatives: A never-ending interaction of melatonin with reactive oxygen and nitrogen species? J. Pineal Res., 2007, 42, 28.
[19]
Yılmaz, A.D.; Coban, T.; Suzen, S. Synthesis and antioxidant activity evaluations of melatonin-based analogue indole-hydrazide/ hydrazone derivatives. J. Enzyme Inhib. Med. Chem., 2012, 27, 428.
[20]
Kareem, H.S.; Ariffin, A.; Nordin, N.; Heidelberg, T.; Abdul-Aziz, A.; Kong, K.W.; Yehye, W.A. Correlation of antioxidant activities with theoretical studies for new hydrazone compounds bearing a 3, 4, 5-trimethoxy benzyl moiety. Eur. J. Med. Chem., 2015, 103, 497.

Rights & Permissions Print Cite
Article Metrics
29
3
© 2024 Bentham Science Publishers | Privacy Policy