Facile one-pot synthesis of pyrimido[4,5-d]pyrimidine-2,4-diones in Ionic Liquid and study of their antibacterial activities

Iranian Journal of Catalysis

مقاله 4، دوره 3، شماره 1، خرداد 2013، صفحه 21-26   

نویسندگان

Ayoob Bazgir¹؛ Seyyedeh Cobra Azimi^{* 2}

¹Department of Chemistry, Shahid Beheshti University, P.O. Box 1983963113, Tehran, Iran.

²Young Researchers Club, Rasht Branch, Islamic Azad University, Rasht, Iran

چکیده

A simple, novel, efficient and three-component procedure for the synthesis of pyrimido[4,5-d]pyrimidine-2,4-dione derivatives by the reaction of 6-amino-1,3-dimethyluracil, aldehyde and 2-benzylisothiourea hydrochloride promoted by ionic liquid 1-butyl-3-methylimidazolium bromide ([BMIm]Br) under solvent-free conditions is reported. The presented method is benefited from operational simplicity, simple workup and reusability of ionic liquid. These products were evaluated in vitro for their antibacterial activities.

کلیدواژه‌ها

Ionic Liquid؛ Pyrimido[4,5-d]pyrimidine-2,4-dione؛ 6-Amino-uracil؛ Antibacterial activities

مراجع

[1] A. Khalafi-Nezhad, B. Mokhtari, Tetrahedron Lett. 45 (2004) 6737-6739.
[2] T. Welton, Chem. Rev. 99 (1999) 2071-2083.
[3] N. Jain, A. Kumar, S. Chauhan, Tetrahedron 61 (2005) 1015-1060.
[4] A.R. Hajipour, I. Mahboobi Dehban, Iran. J. Catal. 2 (2012) 147-151.
[5] A.R. Hajipour, F. Rafiee, Iran. J. catal. 2 (2012) 23-26.
[6] A. Bamoniri, A.R. Pourali, S.M.R. Nazifi, Iran. J. catal. 2 (2012) 185-189.
[7] M.M. Khodaei, A.R. Khosropour, S. Ghaderi, J. Iran. Chem. Soc. 3 (2006) 69-72.
[8] H.Y. Guo , Y.Yu, Chin. Chem. Lett. 21 (2010) 1435-1438.
[9] X. Mi, S. Luo, J.P. Cheng, J. Org. Chem. 70 (2005) 2338-2341.
[10] D.C. Chen, H.Q. Ye, H. Wu, Chin. Chem. Lett. 18 (2007) 27-29.
[11] A. Davoodnia, S. Allameh, A.R. Fakhari, Chin. Chem. Lett. 21 (2010) 550-553.
[12] A. Clark, Pharm Res. 13 (1996) 1133-1141.
[13] R.G. Melik-Ogandzhanyan, V.E. Khachatryan, A.S. Gapoyan, Russ. Chem. Rev. 54 (1985) 262-276.
[14] G.W. Rewcastle, A.J. Bridge, D.W. Fry, J.R. Rubin, W.A. Denny, J. Med. Chem. 40 (1997) 1820-1826.
[15] J.E. Gready, C. McKinlay, M.G. Gebauer, Eur. J. Med. Chem. 38 (2003) 719-728.
[16] Y.S. Sanghhvi, S.B. Larson, S.S. Matsumoto, L. D. Nord, D.F. Smee, R.C. Willis, T. H. Avery, R.K. Robins, G.R. Revankar, J. Med. Chem. 32 (1989) 629-637.

[17] J.P. De la Cruz, T. Carrasco, G. Ortega, F. Sanchez De la Cuesta, Lipid 27 (1992) 192-194.
[18] V.J. Ram, A. Goel, S. Sarkhel, P.R. Maulik, Bioorg. Med. Chem. 10 (2002) 1275-1280.
[19] R.B. Tenser, A. Gaydos, K.A. Hay, Antimicrob. Agents Chemother. 45 (2001) 3657-3659.
[20] E. Campaigne, R.L. Ellis, M. Bradford, J. Ho, J. Med. Chem. 12 (1996) 339-342.
[21] A.I. Diaa, M.E. Amira. E.A. Elham, Arkivoc vii (2009) 12-25.
[22] A. Diaa Eur. J. Med. Chem. 44 (2009) 2776-2781.
[23] M.S. Novikov, O.N. Ivanova, A.V. Ivanov, A.A. Ozerov, V.T. Valuev-Elliston, K. Temburnikar, G.V. Gurskaya, S.N. Kochetkov, C. Pannecouque, J. Balzarini, K.L. Seley-Radtke, Bioorg. Med. Chem. 19 (2011) 5794-5802.
[24] M. Dabiri, S.C. Azimi, H.R. Khavasi, A. Bazgir. Tetrahedron 64 (2008) 7307-7311.
[25] R. Ghahremanzadeh, S.C. Azimi, N. Gholami, A. Bazgir. Chem. Pharm. Bull. 56 (2008) 1617-1620.
[26] M. Dabiri, S.C. Azimi, H. Arvin-Nezhad, Heterocycles 75 (2008) 87-93.
[27] M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, A. Bazgir. Tetrahedron 63 (2007) 1770-1774.
[28] M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, A. Bazgir. J. Heterocycl. Chem. 44 (2007) 1009-1011.
[29] K. Jadidi, R. Ghahremanzadeh, A. Bazgir, Tetrahedron 65 (2009) 2005-2009.
[30] K. Rad-Moghadam, S.C. Azimi, Tetrahedron 68 (2012) 9706-9711.
[31] NCCLS, “Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, which Grows Aerobically,” 5th ed., Approved Standard M7- A5, NCCLS, Villanova, PA, 2000.