Synthesis and Antioxidant Activities of Novel Naphthalimide Derivatives

Year 2021, Volume: 4 Issue: 1, 51 - 58, 31.05.2021

Ufuk Yıldız

https://doi.org/10.34088/kojose.816212

Cited By: 1

https://izlik.org/JA45WG39UD

Abstract

In this study, synthesis and characterization of naphthalimide derivatives containing both amide and urea groups were performed and their antioxidant activities were determined. 4-R-1 8-naphthalic anhydride (R = -H, -NO2 or –NH2) with different functional groups has been chosen as the precursor and reacted with 5,6-diamino-1H-benzo[d]imidazol-2(3H)-one to synthesize the targeted naphthalimide derivatives. ESI-MS and 1H-NMR techniques have been used to characterize the molecules. Antioxidant activities of compounds have been determined by DPPH and peroxide radical scavenging methods.

Keywords

Antioxidant , DPPH , Naphthalimide , Peroxide

Project Number

2019-72118496-02

References

• [1] Cornelli U., 2009.Antioxidant use in nutraceuticals. Clinics in Dermatology 27(2), p. 175-194.
• [2] Giugliano D., Ceriello A., and Paolisso G., 1995.Diabetes mellitus, hypertension, and cardiovascular disease: Which role for oxidative stress? Metabolism 44(3), p. 363-368.
• [3] Reuter S., Gupta S.C., Chaturvedi M.M., and Aggarwal B.B., 2010.Oxidative stress, inflammation, and cancer: How are they linked? Free Radical Biology and Medicine 49(11), p. 1603-1616.
• [4] Saeedi M., Goli F., Mahdavi M., Dehghan G., Faramarzi M.A., Foroumadi A., and Shafiee A., 2014.Synthesis and Biological Investigation of some Novel Sulfonamide and Amide Derivatives Containing Coumarin Moieties. Iran J Pharm Res 13(3), p. 881-92.
• [5] Huczyński A., Janczak J., Stefańska J., Antoszczak M., and Brzezinski B., 2012.Synthesis and antimicrobial activity of amide derivatives of polyether antibiotic—salinomycin. Bioorganic & Medicinal Chemistry Letters 22(14), p. 4697-4702.
• [6] Narasimhan B., Belsare D., Pharande D., Mourya V., and Dhake A., 2004.Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 39(10), p. 827-34.
• [7] Kamat J.P. and Devasagayam T.P., 1999.Nicotinamide (vitamin B3) as an effective antioxidant against oxidative damage in rat brain mitochondria. Redox report : communications in free radical research 4(4), p. 179-184.
• [8] Malki F., Touati A., and Moulay S. Comparative Study of Antioxidant Activity of Some Amides. 2017.
• [9] Yonova P.A. and Stoilkova G.M., 2004.Synthesis and biological activity of urea and thiourea derivatives from 2-aminoheterocyclic compounds. Journal of Plant Growth Regulation 23(4), p. 280-291.
• [10] Abdel-Rahman H.M. and Morsy M.A., 2007.Novel benzothiazolyl urea and thiourea derivatives with potential cytotoxic and antimicrobial activities. Journal of Enzyme Inhibition and Medicinal Chemistry 22(1), p. 57-64.
• [11] Shusheng Z., Tianrong Z., Kun C., Youfeng X., and Bo Y., 2008.Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents. European Journal of Medicinal Chemistry 43(12), p. 2778-2783.
• [12] Özgeriş B., Akbaba Y., Özdemir Ö., Türkez H., Göksu S., 2017. Synthesis and Anticancer Activity of Novel Ureas and Sulfamides Incorporating 1-Aminotetralins. Archives of Medical Research 48 (6), p. 513-519.
• [13] Özgeriş B., 2021. Design, synthesis, characterization, and biological evaluation of nicotinoyl thioureas as antimicrobial and antioxidant agents. The Journal of Antibiotics. https://doi.org/10.1038/s41429-020-00399-7
• [14] Aksu K., Özgeriş B., Taslimi P., Naderi A., Gülçin İ., and Göksu S., 2016.Antioxidant Activity, Acetylcholinesterase, and Carbonic Anhydrase Inhibitory Properties of Novel Ureas Derived from Phenethylamines. Archiv der Pharmazie 349(12), p. 944-954.
• [15] Bhaskara Reddy M.V., Srinivasulu D., Peddanna K., Apparao C., and Ramesh P., 2015.Synthesis and Antioxidant Activity of New Thiazole Analogues Possessing Urea, Thiourea, and Selenourea Functionality. Synthetic Communications 45(22), p. 2592-2600.
• [16] Özel A., Barut B., Demirbaş Ü., and Biyiklioglu Z., 2016.Investigation of DNA binding, DNA photocleavage, topoisomerase I inhibition and antioxidant activities of water soluble titanium(IV) phthalocyanine compounds. Journal of Photochemistry and Photobiology B: Biology 157, p. 32-38.
• [17] Al-Amiery A.A., Al-Majedy Y.K., Kadhum A.A.H., and Mohamad A.B., 2015.Hydrogen Peroxide Scavenging Activity of Novel Coumarins Synthesized Using Different Approaches. PLOS ONE 10(7), p. e0132175.
• [18] Soare J.R., Dinis T.C.P., Cunha A.P., and Almeida L., 1997.Antioxidant Activities of Some Extracts of Thymus zygis. Free Radical Research 26(5), p. 469-478.
• [19] Blois M.S., 1958.Antioxidant Determinations by the Use of a Stable Free Radical. Nature 181(4617), p. 1199-1200.