Synthesis and Antioxidant Properties of Two New Derivatives of Indeno-Benzofuran
محورهای موضوعی :shiva khalil_moghaddam 1 , Ashraf Sadat Shahvelayati 2 , Atousa Aliahmadi 3
1 - Assistant Professor of Biochemistry, Young Researchers and Elite Club, Yadegar - e- Imam Khomeini (RAH) shahr-e-Rey Branch, Islamic Azad University, Tehran, Iran
2 - Associate Professor of Organic Chemistry, Young Researchers and Elite Club, Yadegar - e- Imam Khomeini (RAH) shahr-e-Rey Branch, Islamic Azad University, Tehran, Iran
3 - Assistant Professor of Microbiology, Medicinal Plants and Drug Research Institute, Shahid Beheshti University, Tehran, Iran
کلید واژه: Antioxidant, Ninhydrin, Pyrogallol, Mono-adduct, Bis-adduct, Acetic Ionic Liquid,
چکیده مقاله :
Ninhydrin reacts with poly-phenols in different ratios to produce tetracyclic adducts. Here, pyrogallol was used as a polyphenol compound. In the company of acidic ionic liquid (AIL), there was a selective reaction between the ortho-site of polyphenol and the ninhydrin’s carbonyl group. Mono-adduct (1:1) 3 and bis-adduct (2:1) 4 were prepared as a solvent and a catalyst for the reaction of ninhydrin with pyrogallol in 1-(carboxymethyl)-3-methyl-1H-imidazolium chloride (mcmimCl). Purity of the products was approved by 1H NMR, 13C NMR, IR and Mass Spectroscopy. Moreover, the antioxidant activity of novel derivatives investigated in this paper by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical assay and butylated hydroxytoluene (BHT) was considered to be standard. The results indicated that mono-adduct showed the strongest antioxidant activity (IC50 = 5.289µg/ml).
1. Wasserscheid P., Welton T., 2003. Ionic liquids in synthesis, Wiley, Weinheim.
2. Yavari I., Kowsari E., 2007. Ionic liquids as novel and recyclable reaction media for N-alkylation of amino-9,10-anthraquinones by trialkyl phosphites, Tetrahedron Lett. 48, 3753-3756.
3. Yavari I., Shahvelayati A.S., Ghanbari M., Ghazvini M., Piltan M., 2011. One-pot synthesis of functionalized α-acyloxythioamides from N-Protected a-amino acids as an acid component in the passerini reaction in an ionic liquid. J Iran Chem Soc. 8, 636-642
4. Shahvelayati A.S., Esmaeeli Z., 2012. Efficient synthesis of S-dipeptidothiouracil derivatives via a one-pot, five-component reactionunder ionic liquid condition. J Sulfur Chem. 33, 319-325.
5. Amarasekara A.S., 2016. Acidic Ionic Liquids. Chem Rev. 116(10), 6133-6183.
6. Vygodskii Y.S., Lozinskaya E.I., Shaplov A.S., 2002. Macromol Rapid Commun.23,676–679.
7. Rindhe S.S., Rode M., Karale B.K., 2010. New benzofuran derivatives as an antioxidant agent, Indian J. Pharm Sci. 27, 231-235.
8. Alwin, T., Reji T., 2017. Synthesis Antioxidant and Antibacterial Studies on 2-(2-arylamino-4-phenylthiazol-5-yl)benzofuran Derivatives. Int Res J Pure Appl Chem. 15(1), 1-8.
9. Chand K., Rajeshwari., Hiremathad A., Singh M., Santos MA., Keri RS., 2017. A review on antioxidant potential of bioactive heterocycle benzofuran: Natural and synthetic derivatives. Pharmacol Rep. 69, 281-295.
10. Naik R., Harmalkar DS., Xu X., Jang K., Lee K., 2015. Bioactive benzofuran derivatives: Moracins A-Z in medicinal chemistry. Eur J Med Chem. 90, 379-393.
11. Rangaswamy J., Kumar HV., Harini ST., Naik N., 2012. Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility, Bioorganic and Medicinal Chemistry Letters. Bioorganic Med Chem Lett. 22, 4773-4777.
12. Yadav A., Yadav A., Kumari R., Mishra J.P., 2016. Antioxidants and its Functions in Human Body- A Review, Res. Environ Life Sci. 9, 1328-1331.
13. Sarvajeet G., Narendra S.T., 2010. Reactive oxygen species and antioxidant machinery in abiotic stress tolerance in crop plants. Plant Physiol Biochem. 48, 909-930.
14. Matés., José M. Pérez-Gómez., Cristina De Castro I.N., 1999. Antioxidant enzymes and human diseases, Clin Biochem. 32, 595-603.
15. Blokhina O., Virolainen E., Fagerstedt K., 2002. Antioxidants, oxidative damage and oxygen deprivation stress- A review, Ann Bot.91, 179-194.
16. Kunwar A., 2011. Free radicals, oxidative stress and importance of antioxidants in human health Amit. J Med Allied Sci. 1(2), 53-60.
17. Huang D.J., Prior R.l., 2005. The chemistry behind antioxidant capacity assays. J Agric Food chem. 53, 1841-1856.
18. Vygodskii Y.S., Lozinskaya E.I., Shaplov A.S., 2002. Ionic Liquids as Novel Reaction Media for the Synthesis of Condensation Polymers. Macromol Rapid Commun. 23,676–679.
19. Esmaeili M., Sonboli A., Ayyari Noushabadi M., 2010. Antioxidant and protective properties of six Tanacetum species against hydrogen peroxide-induced oxidative stress in K562 cell line: A comparative study. Food Chem. 121, 148-155.
20. Dastan D., Aliahmadi A., 2015. Antioxidant and antibacterial studies on different extracts of Ornithogalum cuspidatum Bertol from Iran. BFAIJ. 7(2), 1027-1072.
