Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, Iran

2 Department of Biology, Faculty of Natural Sciences, University of Tabriz, Tabriz-Iran

Abstract

A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the presence of triethylamine. The structure of the acrylate monomer was established on the basis of FT-IR, 1H NMR, 13C NMR, MS and elemental analysis. This monomer was polymerized using 2,2´-azobisisobutyronitrile (AIBN) as the initiator in N,N-dimethylformamide solution. Thermal stability of the polymer was investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The synthesized compounds were evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria using the disk diffusion method. The results of antibacterial assay indicated that these compounds exhibited moderate bactericidal activity.

Graphical Abstract

Keywords

Main Subjects

[1] M. Aufort, J. Herscovici, P. Bouhours, N. Moreau, C. Girard, Bioorg. Med. Chem. Lett., 2008, 18, 1195-1198.

[2] D.R. Buckle, C.J.M. Rockell, H. Smith, B.A. Spicer, J. Med. Chem., 1986, 29, 2262- 2267.

[3] N.G. Aher, V.S. Pore, N.N. Mishra, A. Kumar, P.K. Shukla, A. Sharma, M.K. Bhat,  Bioorg. Med. Chem. Lett., 2009, 19, 759-763.

[4] K. Kushwaha, N. Kaushik, Lata, S.C. Jain, Bioorg. Med. Chem. Lett., 2014, 24, 1795-1801.

[5] R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. De Clercq, C.F. Perno, A. Karlsson, J. Balzarini, M.J. Camarasa, J. Med. Chem., 1994, 37, 4185- 4194.

[6] Y.W. He, C.Z. Dong, J.Y. Zhao, L.L. Ma, Y.H. Li, H.A. Aisa, Eur. J. Med. Chem., 2014, 76, 245- 255.

[7] J. Khazir, I. Hyder, J.L. Gayatri, L. Prasad Yandrati, N. Nalla, G. Chasoo, A. Mahajan, A.K. Saxena, M.S. Alam, G.N. Qazi, H.M. Sampath Kumar, Eur. J. Med. Chem., 2014, 82, 55-262.

[8] P. Sambasiva Rao, C. Kurumurthy, B. Veeraswamy, G. Santhosh Kumar, Y. Poornachandra, C. Ganesh Kumar, Vasamsetti Sathish Babu, Kotamraju Srigiridhar, B. Narsaiah, Eur. J. Med. Chem., 2014, 80, 184-191.

[9] L.V. Lee, M.L. Mitchell, S.J. Huang, V.V. Fokin, K.B. Sharpless, C.H. Wong, J. Am. Chem. Soc., 2003, 125, 9588-9589.

[10] Q. Wang, T.R. Chan, R. Hilgraf, V.V. Fokin, K.B. Sharpless, M.G. Finn, J. Am. Chem. Soc., 2003, 125, 3192–3193.

[11] A. Devadoss, C.E.D. Chidsey, J. Am. Chem. Soc., 2007,129, 5370-5371.

[12] W.Q. Fan, A.R. Katritzky, In Comprehensive Heterocyclic Chemistry II; A.R. Katritzky, C.W. Rees, E.F.V. Scriven, (Eds.), Elsevier Science: Oxford, 1996, 4, 1-126.

[13] K. Odlo, E.A. Høydahl, T.V. Hansen,  Tetrahedron Lett., 2007, 48, 2097-2099.

[14] W.J. Evans, E. Montalvo, T.M. Champagne, J.W. Ziller, A.G. DiPasquale, A.L. Rheingold, J. Am. Chem. Soc., 2008, 13, 16-17.

[15] A. Pavani, T.L. Viveka, J. Appl. Chem., 2013, 3, 36-41.

[16] R. Huisgen, In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A Ed.; Wiley-Interscience: New York, 1984, 1, 1-176.

[17] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed., 2002, 41, 2596-2599.

[18] C.W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem., 2002, 67, 3057-3064.

[19] F. Caturla, M. Amat, R.F. Reinoso, E. Calaf, G. Warrellow, Bioorg. Med. Chem. Lett., 2006, 16, 3605-3608.

[20] T. Takemura, I. Hayakawa, E. Fukasawa, T. Sengoku, H. Kigoshi, Tetrahedron, 2012, 68, 6477-6484.

[21] D.T. Puerta, J. Mongan, B.L. Tran, J.A. McCammon, S.M. Cohen, J. Am. Chem. Soc., 2005, 127, 14148-14149.

[22] Y. Matsumura, K. Shirai, T. Maki, Y. Itakura, Y. Kodera, Tetrahedron Lett., 1998, 39, 2339-2340.

[23] D. Garey, M.L. Ramirez, S. Gonzales, A. Wertsching, S. Tith, K. Keefe, M.R. Peña, J. Org. Chem., 1996, 61, 4853-4856.

[24] O. Kayser, A.F. Kiderlen, S.L. Croft, Acta Trop., 2003, 86, 105-107.

[25] M.S. South, C.C. Ma, K.J. Koeller, U.S. Patent 6916847, 2001; Chem. Abstr., 135, 303776e.

[26] M.D. Aytemir, D.D. Erol, R.C. Hider, M. Özalp, Turk. J. Chem., 2003, 27, 757-764.

[27] M.D. Aytemir, E. Septioğlu, Ü. Ҫaliş,  Arzneim. Forsch., 2010,  60 , 22-29

[28] S. Urano, K. Aoki, N. Tsuboniwa, R. Mizuguchi, O. Tsuge, Prog. Org. Coat., 1992, 20, 471-486.

[29] A. Akelah, A. Moel, Functionalized polymer and their applications, 1990, Thompson, New Delhi.

[30] E.C. Buruiana, M. Zamfir, T. Buruiana, Eur. Polym. J., 2007, 43, 4316-4324.

[31] M.Z. Elsabee, E.A. Ali, S.M. Mokhtar, M. Eweis, React. Funct. Polym., 2011, 71, 1187-1194.

[32] B. Eftekhari-Sis, F. Ghahramani, Des. Monomers Polym., 2015, 18, 460-469.

[33] G. Gratzl, C. Paulik, S. Hild, J.P. Guggenbichler, M. Lackner, Mater. Sci. Eng., C. Mater. Biol. Appl., 2014, 38, 94-100.

[34] O. Vogl, J. Mac. Sci. Part A., 1996, 33, 1571-1579.

[35] B. Saha, M. Streat, React. Funct. Poly., 1999, 40, 13-27.

[36] G. Luengo, J. Pan, M. Heuberger, J.N. Israelachvili, Langmuir, 1998, 14, 3873-3881.

[37] N. Lakhera, A. Graucob, A.S. Schneider, E. Kroner, E. Arzt, C. M. Yakacki, C.P. Frick, Int. J. Adhes. Adhes., 2013, 44, 184-194.

[38] K. Nollenberger, J. Albers, Int. J. Pharm., 2013, 457, 461-469.

[39] A.S. Brar, M. Malhotra, Macromolecules, 1996, 29, 7470-7476.

[40] H. Omidian, S.A. Hashemi, P.G. Sammes, I. Meldrum, Polym., 1999, 40, 1753-1761.

[41] A. Lungu, D.C. Neckers, J. Coat. Technol., 1995, 67, 29-35.

[42] A. Massoudi, A. Louie, O. Louie, Iran. Chem. Commun., 2015, 3, 276-282.

[43] S. Balamurugan, S. Nithyanandan, C. Selvarasu, G.Y. Yeap, P. Kannan, Polym.,  2012, 53, 4104-4111.

[44] C. Li, H. Liu, Y. Li, Macromol. Chem. Phys., 2011, 212, 1050-1055.

[45] M.L. Miles, T.M. Harris, C.R. Hauser, J. Org. Chem., 1965, 30, 1007-1011.

[46] M.G. Marei, M.M. Mishrikey, I.E. El-Kholy, Indian. J. Chem., Sect B, 1987, 26, 163-165.

[47] M. Saraei, B. Eftekhari-Sis, M. Faramarzi, R. Hossienzadeh, J. Heterocycl. Chem., 2014, 51, 1500-1503.

[48] M. Saraei, R. Hossienzadeh, M. Jabbari, Heterocycl. Commun., 2015, 21, 103-107.