Synthesis of pyrazolopyranopyrimidines catalyzed by caffeine supported on boehmite nanoparticles and their evaluation for anti-bacterial activities
محورهای موضوعی : Iranian Journal of CatalysisMohammad Bakherad 1 , Rahele Doosti 2 , Mahdi Mirzaee 3 , Khosrow Jadidi 4
1 - School of Chemistry, Shahrood University of Technology, Shahrood 3619995161, Iran
2 - School of Chemistry, Shahrood University of Technology, Shahrood 3619995161, Iran
3 - School of Chemistry, Shahrood University of Technology, Shahrood 3619995161, Iran
4 - Department of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran.
کلید واژه: Reusable catalyst, Anti-bacterial activity, Caffeine, Boehmite nanoparticles, Pyrazolopyranopyrimidine,
چکیده مقاله :
The reaction of 3-chloropropyl boehmite nanoparticles with caffeine and sulfuric acid afforded BNPs-3-propyl-imidazolopyridinium hydrogen sulfate [BNPs-Caff]HSO4 as a new BNPs-supported ionic liquid (IL) catalyst. [BNPs-Caff]HSO4 proved to be an efficient heterogeneous catalyst for the synthesis of pyrazolopyranopyrimidines via a one-pot four-component reaction of hydrazine hydrate, ethyl acetoacetate, barbituric acid, and an aldehyde. The attractive features of this method are simple procedure, clean reaction, use of a reusable catalyst, easy workup, and performing a multi-component reaction (MCR) in water. A number of synthesized compounds were screened for their in vitro anti-bacterial activities against the Gram-positive and Gram-negative bacteria using a well-diffusion method.
[1] Y.P. Liu, J.M. Liu, X. Wang, Tetrahedron. 69 (2013) 5242-5247.
[2] H. Gao, J. Sun, C.-G. Yan, Tetrahedron 69 (2013) 589-594.
[3] Y. Li, Q.Y. Li, H.W. Xu, Tetrahedron. 69 (2013) 2941-2946.
[4] Z. Ismail, G. Aly, M. El-Degwi, H. Heiba, M. Ghorab, Egypt. J. Biotechnol. 13 (2003) 73-82.
[5] F.M. Abdelrazek, P. Metz,. O. Kataeva, A. Jaeger, Arch. Pharm. 340 (2007) 543-548.
[6] N.R. Mohamed, N.Y. Khaireldin, A.F. Fahmy, A.A. El-Sayed, Der. Pharma. Chem. 2 (2010) 400-410.
[7] J.A. Valderrama, P. Colonelli, D. Vásquez, M.F. Gonzalez, J.A. RodrÃguez, C. Theoduloz, Bioorg. Med. Chem. 16 (2008) 10172-10181.
[8] M.C. Bagley, D.D. Hughes, M.C. Lubinu, E.A. Merritt, P.H. Taylor, N.C. Tomkinson, QSAR Comb. Sci. 23 (2004) 859-867.
[9] N.R. Kamdar, D.D. Haveliwala, P.T. Mistry, S.K. Patel, Eur. J. Med. Chem. 45 (2010) 5056-5063.
[10] M.M. Heravi, F. Mousavizadeh, N. Ghobadi, M. Tajbakhsh, Tetrahedron. Lett. 5 (2014) 1226-1228.
[11] X.T. Li, A.D. Zhao, L.P. Moa, RSC Adv. 4 (2014) 51580-51585.
[12] S. Dastkhoon, Z. Tavakoli, S. Khodabakhshi, M. Baghernejad, M.K. Abbasabadi, New J. Chem. 39 (2015) 7268-7271.
[13] S. Khodabakhshi, A. M. Rashidi, Z. Tavakoli, Monatsh. Chem. 147 (2016) 791-795.
[14] A. Ganesan, J. Kothandapani, S.G. Subramaniapillai, RSC Adv. 6 (2016) 20582- 20587.
[15] F. Rigi, H.R. Shaterian, J. Chin. Chem. Soc. 63 (2016) 557-561.
[16] P. Wassercheid, T. Welton, Ionic Liquids in Synthesis, 2nd ed., Wiley-VCH, Weinheim, (2007).
[17] P.P. Salvi, A.M. Mandhare, A.S. Sartape, D.K. Pawar, S. H. Han, S.S. Kolekar, C.R. Chim. 14 (2011) 883-886.
[18] N. Ghaffari Khaligh, J. Mol. Catal. A: Chem. 349 (2011) 63-70.
[19] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat- Zadeh, A. Hasaniniejad, A.A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon , R. Roohandeh, J. Mol. Liq. 167 (2012) 69-77.
[20] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A 400 (2011) 1365-1371.
[21] Y. Liu, M. Li , Y. Lu , G.H. Gao, Q. Yang, M.Y He, Catal. Commun. 7 (2006) 985-989.
[22] S. Luo, X. Mi , L. Zhang , S. Liu , H. Xu , J. P. Cheng, Angew. Chem. Int. Ed. 45 (2006) 3093-3097.
[23] J.M. Xu, B.K. Liu , W.B. Wu, C. Qian, Q. Wu , X.F. Lin, J. Org. Chem. 71 (2006) 3991-3993.
[24] C. Paun, J. Barklie , P. Goodrich, H. Gunaratne, A. McKeown, V. Parvulescu, C. Hardacre, J. Mol. Catal. A: Chem. 269 (2007) 64-71.
[25] D.J. Macquarrie, Chem. Commun. 10 (1997) 601-602.
[26] M.M. Amini, M. Mirzaee, J. Sol-Gel Sci. Technol. 36 (2005)19-23.
[27] M. Mirzaee, B. Bahramian, A. Amoli, Appl. Organomet. Chem. 29 (2015) 593-600.
[28] M. Mirzaee, B. Bahramian, J. Gholizadeh, A. Feizi, R. Gholami, Chem. Eng. J. 308 (2017) 160-168.
[29] A. Ghorbani-Choghamarani, B. Tahmasbi, F. Arghand, S. Faryadi, RSC Adv. 5 (2015) 92174-92183.
[30] M. Hajjami, A. Ghorbani-Choghamarani, R. Ghafouri-Nejad, B. Tahmasbi, New J. Chem. 40 (2016) 3066-3074.
[31] A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, RSC Adv. 6 (2016) 56638-56646.
[32] A. Ghorbani-Choghamarani, B. Tahmasbi, F. Arghand, S. Faryadi, RSC Adv. 5 (2015) 92174-92183.
[33] H. Ashihara, A.M. Monteiro, F.M. Gillies, A. Crozier, Plant Physiol. 111 (1996) 747-753.
[34] J. Schütz, W.A. Herrmann, J. Organomet. Chem. 689 (2004) 2995-2999.
[35] A. Kascatan-Nebioglu, M.J. Panzner, J.C. Garrison, C.A. Tessier, W.J. Youngs. 23 (2004) 1928-1931.
[36] F.T. Luo, H.K. Lo, J. Organomet. Chem. 696 (2011) 1262-1265.
[37] A. Keivanloo, M. Bakherad, E. Imanifar, M. Mirzaee, Appl. Catal. A 467 (2013) 291-300.
[38] A. Shamroukh, M. Zaki, E. Morsy, F. Abdel-Motti, F. Abdel-Megeid, Arch. Pharm. Chem. Life Sci. 345 (2007) 340-351.
