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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Synthesis and Evaluation of Antioxidant, Antimicrobial and Anticancer Properties of 2-(Prop-2-yn-1-yloxy)benzaldehyde Derivatives

Author(s): Metin Konus*, Selahattin Aydemir, Can Yilmaz, Arif Kivrak, Aslihan Kurt Kizildogan and Pembegül Uyar Arpacı

Volume 16, Issue 5, 2019

Page: [415 - 423] Pages: 9

DOI: 10.2174/1570178616666181116100232

Price: $65

Abstract

5-bromo-2-(prop-2-yn-1-yloxy)benzaldehyde (compound 3) and 3,5-di-tert-butyl-2-(prop-2- yn-1-yloxy)benzaldehyde (compound 5) were synthesized via nucleophilic substitution reactions. Compound 5 showed higher antioxidant capacity with respect to compound 3 in all the four different antioxidant activity methods used. Moreover, in phosphomolybdenum assay, compound 5, with 1.1 proportion value, showed almost the same total antioxidant capacity compared to universal trolox standard. Furthermore, Broth microdilution method and agar disc diffusion tests demonstrated that the same compound also exhibited good antibacterial activity towards the bacteria Bacillus subtilis. Finally, both of the benzaldehyde compounds showed high antifungal activity against Aspergillus niger. In this study, compound 5 (IC50: 54.3 µg/ml) showed significant cytotoxic activity against breast adenocarcinoma cell line MCF-7 with respect to compound 3 (IC50: 173.4 µg/ml).

Keywords: 2-(prop-2-yn-1-yloxy)benzaldehyde, antioxidant, antibacterial, antifungal, anticancer, human breast carcinoma.

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[1]
Le Goff, G.; Ouazzani, J. Bioorg. Med. Chem., 2014, 22, 6529-6544.
[2]
Fang, X.B.; Fang, L.; Gou, S.H. Chin. J. Org. Chem., 2012, 3(7), 1217-1231.
[3]
Scognamiglio, J.; Jones, L.; Vitale, D.; Letizia, C.S.; Api, A.M. Food Chem. Toxicol., 2012, 50, 140-160.
[4]
Arteaga, J.F. Ruiz- Montoya, M.; Palma, A.; Alonso- Garrido, G.; Pintado, S.; Rodriguez-Mellado, J.M. Molecules, 2012, 17, 5126-5138.
[5]
Nguyen, D.T.; Le, T.H.; Trang-Bui, T.T. Eur. J. Med. Chem., 2013, 60, 199-207.
[6]
Ariyoshi-Kishino, K.; Hashimoto, K.; Amano, O.; Saitoh, J.; Kochi, M.; Sakagami, H. Anticancer Res., 2010, 30(12), 5069-5076.
[7]
Bassi, A.M.; Penco, S.; Canuto, R.A.; Muzio, G.; Ferro, M. Drug Chem. Toxicol., 1997, 20(3), 173-187.
[8]
Fu, Y.; Zhou, S.; Liu, Y.; Yang, Y.; Sun, X.; Li, C. BioMed Res. Int., 2014, 2014, 5270422014.
[9]
Faria, N.C.G.; Kim, J.H.; Gonçalves, L.A.P.; Martins, M.L.; Chan, K.L.; Campbell, B.C. Lett. Appl. Microbiol., 2011, 52, 506-513.
[10]
Kim, J.H.; Chan, K.L.; Mahoney, N.; Campbell, B. J. Ann. Clin. Microbiol. Antimicrob., 2011, 10, 23.
[11]
Friedman, M.; Henika, P.R.; Madrell, R.E. J. Food Prot., 2003, 66, 1811-1821.
[12]
Wang, J.; Liu, H.; Zhao, J.; Gao, H.; Zhou, H.; Liu, Z.; Chen, Y.; Sui, P. Molecules, 2010, 15, 5807-5817.
[13]
Butzenlechner, M.; Rossmann, A.; Schmidt, H.L. J. Agric. Food Chem., 1989, 37, 410-412.
[14]
Wang, W.; Kannan, P.; Xue, J.; Kannan, K. Environ. Res., 2016, 151, 339-343.
[15]
Lobo, V.; Patil, A.; Phatak, A.; Chandra, N. Pharmacogn. Rev., 2010, 4(8), 118-126.
[16]
Barber, D.A.; Harris, S.R. Am. Pharm., 1994, (34), 26-35.
[17]
Berdy, J. J. Antibiot., 2012, 65, 385-395.
[18]
WHO. 2016. http://www.who.int/news-room/fact-sheets/detail/the-top-10-causes-of-death (Accessed October 19, 2018)
[19]
Essien, E.E.; Newby, J.S.; Walker, T.M.; Setzer, W.N.; Ekundayo, O. Medicines, 2016, 3(1), 1.
[20]
Fernandes, R.; Amador, P.; Prudencio, C. Rev. Med. Microbiol., 2013, 24, 7-17.
[21]
Loch, C.; Reusch, H.; Ruge, I.; Godelman, R.; Pflaum, T.; Kuballa, T.; Schumacher, S.; Lachenmeier, D.W. Food Chem., 2016, 206, 74-77.
[22]
Ullah, I.; Khan, A.L.; Ali, L.; Khan, A.R.; Waqas, M.; Hussain, J.; Lee, I.J.; Shin, J.H. J. Microbiol., 2015, 53(2), 127-133.
[23]
Ouahrouch, A.; Ighachane, H.; Taourirte, M.; Engels, J.W.; Sedra, M.H.; Lazrek, H.B. Arch. Pharm. (Weinheim), 2014, 347(10), 748-755.
[24]
Tiwari, S.; Pathak, P.; Singh, K.P.; Sagar, R. Bioorg. Med. Chem. Lett., 2017, 27, 3802-3805.
[25]
Bera, K.; Sarkar, S.; Biswas, S.; Maiti, S.; Jana, U. J. Org. Chem., 2011, 76(9), 3539-3544.
[26]
Wu, X.; Beecher, G.R.; Holden, J.M.; Haytowitz, D.B.; Gebhardt, S.E.; Prior, R.L. J. Agric. Food Chem., 2004, 52(12), 4026-4037.
[27]
Prieto, P.; Manuel, P.; Miguel, A. Anal. Biochem., 1999, 269(2), 337-341.
[28]
Meir, S.; Kanner, J.; Akiri, B.; Hadas, S.P. J. Agric. Food Chem., 1995, 43, 1813-1819.
[29]
Yen, G.C.; Chen, H.Y. J. Agric. Food Chem., 1995, 43, 27-32.
[30]
Person, A.K.; Chudgar, S.M.; Norton, B.L.; Tong, B.C.; Stout, J.E. J. Med. Microbiol., 2010, 59(Pt 7), 834-838.
[31]
Khoshkholgh, M.J.; Balalaie, S.; Gleiter, R.; Rominger, F. Tetrahedron, 2008, 64, 10924-10929.
[32]
Blois, M.S. Nature, 1958, 181, 1199-1200.
[33]
Coruh, N.; Ozdogan, N. J. Liq. Chromatogr. Relat. Technol., 2014, 37, 1334-1350.
[34]
Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radic. Biol. Med., 1999, 26, 1231-1237.
[35]
Oyaizu, M. Jpn. J. Nutr., 1986, 7, 307-315.
[36]
Desai, R.M.; Dodiya, D.K.; Trivedi, A.R.; Shah, V.H. Med. Chem. Res., 2008, 17(8), 495-506.
[37]
Gu, W.; Wang, S. Eur. J. Med. Chem., 2010, 45(10), 4692-4696.
[38]
Zengin, G.; Sarikurkcu, C.; Uyar, P.; Aktumsek, A.; Uysal, S.; Kocak, M.S.; Ceylan, R. J. Funct. Foods, 2015, 17, 698-708.

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