Fast one-pot synthesis of 1,8-dioxo-decahydroacridine derivatives using sulfonic acid functionalized LUS-1 and the study on their antimicrobial activities
محورهای موضوعی : Iranian Journal of Catalysis
Ghodsi Mohammadi Ziarani
1
(Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran.)
Mahshid Rahimifard
2
(Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran.)
Alireza Badiei
3
(School of Chemistry, College of Science, University of Tehran, Tehran, Iran.)
Ali Abolhasani Soorki
4
(ACECR-Research Institute of Applied Sciences, Shahid Beheshti University, Tehran, Iran.)
کلید واژه: Dimedone, Sulfonic acid functionalized LUS-1, Acridine-1, 8-dione, Nanoporous acid catalyst,
چکیده مقاله :
Mesoporous silica LUS-1 (Laval University Silica) was successfully functionalized by propyl sulfonic acid and was used as a recyclable catalyst for the synthesis of acridine-1,8-diones via a pseudo four component reaction of aromatic aldehydes, dimedone and ammonium acetate (or anilines). The excellent yields, short reaction time, simple work-up procedure, and environmentally friendly conditions are advantages of this method. All synthesized compounds were screened for antimicrobial and antifungal activities. Only compound 3e exhibited activity against Bacillus subtilis.
[1] W.M. Van Rhijn, D.E. De Vos, B.F. Sels, W.D. Bossaert, P.A. Jacobs, Chem. Commun. (1998) 317-318.
[2] B. Das, K. Venkateswarlu, H. Holla, M. Krishnaiah, J. Mol. Catal. A: Chem. 253 (2006) 107-111.
[3] M. Onaka, N. Hashimoto, Y. Kitabata, R. Yamasaki, Appl. Catal. A 241 (2003) 307-317.
[4] R.I. Kureshy, I. Ahmad, K. Pathak, N.H. Khan, S.H.R. Abdi, R.V. Jasra, Catal. Commun. 10 (2009) 572-575.
[5] B. Karimi, D. Zareyee, Org. Lett. 10 (2008) 3989-3992.
[6] G. Mohammadi Ziarani, N. Lashgari, A. Badiei, J. Mol. Catal. A: Chem. 397 (2015) 166-191.
[7] L. Bonneviot, M. Morin, A. Badiei Mesostructured metal or non-metal oxides and method for making same, US patent (2003) 0133868 A1.
[8] P. Reinert, B. Garcia, C. Morin, A. Badiei, P. Perriat, O. Tillement, L. Bonneviot, Stud. Surf. Sci. Catal. 146 (2003) 133-136.
[9] R. Janis, P. Silver, D. Triggle, Adv. Drug Res. 16 (1987) 309-591.
[10] D. Vo, W.C. Matowe, M. Ramesh, N. Iqbal, M.W. Wolowyk, S.E. Howlett, E.E. Knaus, J. Med. Chem. 38 (1995) 2851-2859.
[11] H.-J. Timpe, S. Ulrich, S. Ali, J. Photochem. Photobio. A: Chem. 61 (1991) 77-89.
[12] H. Timpe, S. Ulrich, C. Decker, J. Fouassier, Macromolecules 26 (1993) 4560-4566.
[13] P. Murugan, P. Shanmugasundaram, V. Ramakrishnan, B. Venkatachalapathy, N. Srividya, P. Ramamurthy, K. Gunasekaran, D. Velmurugan, J. Chem. Soc. Perkin Trans. 2 (1998) 999-1004.
[14] M. Kidwai, D. Bhatnagar, Tetrahedron Lett. 51 (2010) 2700-2703.
[15] W. Shen, L.M. Wang, H. Tian, J. Tang, J.J. Yu, J. Fluorine Chem. 130 (2009) 522-527.
[16] M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, Catal. Commun. 9 (2008) 939-942.
[17] K. Niknam, F. Panahi, D. Saberi, M. Mohagheghnejad, J. Heterocycl. Chem. 47 (2010) 292-300.
[18] T.S. Jin, J.S. Zhang, T.T. Guo, A.Q. Wang, T.S. Li, Synthesis (2004) 2001-2005.
[19] K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun. 39 (2009) 228-241.
[20] G. Mohammadi Ziarani, S. Asadi, A. Badiei, S. Mousavi, P. Gholamzadeh, Res. Chem. Intermed. 41 (2015) 637-645.
[21] G. Mohammadi Ziarani, A. Badiei, M. Haddadpour, Int. J. Chem. 3 (2011) 87-94.
[22] G. Mohammadi Ziarani, A. Badiei, Y. Khaniania, M. Haddadpour, Iran. J. Chem. Chem. Eng. 29 (2010) 1-10.
[23] P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, Z. Bahrami, Eur. J. Chem. 3 (2012) 279-282.
[24] G. Mohammadi Ziarani, A. Badiei, Z. Dashtianeh, P. Gholamzadeh, N. Hosseini Mohtasham, Res. Chem. Intermed. 39 (2013) 3157-3163.
[25] P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, A. Abolhassani Soorki, N. Lashgari, Res. Chem. Intermed. 39 (2013) 3925-3936.
[26] G. Mohammadi Ziarani, N. Lashgari, A.R. Badiei, Sci. Iran. 20 (2013) 580-586.
[27] G. Mohammadi Ziarani, S. Faramarzi, S. Asadi, A. Badiei, R. Bazl, M. Amanlou, DARU J. Pharm. Sci. 21 (2013) 3-13.
[28] P. Hashemi, A. Badiei, M. Shamizadeh, G. Mohammadi Ziarani, A.R. Ghiasvand, J. Chin. Chem. Soc. 59 (2012) 727-732.
[29] R. Rezaei, R. Khalifeh, M. Rajabzadeh, L. Dorosty, M.M. Doroodmand, Heterocycl. Commun. 19 (2013) 57-63.
[30] A. Pyrko, Russ. J. Org. Chem. 44 (2008) 1215-1224.
[31] S. Rostamizadeh, A. Amirahmadi, N. Shadjou, A.M. Amani, J. Heterocycl. Chem. 49 (2012) 111-114.
[32] G. Mohammadi Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arabian J. Chem. 7 (2014) 335-339.
[33] X. Fan, Y. Li, X. Zhang, G. Qu, J. Wang, Heteroatom Chem. 18 (2007) 786-790.
[34] G.-W. Wang, J.-J. Xia, C.-B. Miao, X.-L. Wu, Bull. Chem. Soc. Jpn. 79 (2006) 454-459.
[35] S.-H. Li, C. Tang, Asian J. Chem. 23 (2011) 4900-4902.
[36] M. Mokhtary, S. Mirfarjood Langroudi, Monatsh. Chem. 145 (2014) 1489-1494.
[37] M. Nikpassand, M. Mamaghani, K. Tabatabaeian, Molecules 14 (2009) 1468-1474.
[38] A. Heydari, S. Khaksar, M. Tajbakhsh, H.R. Bijanzadeh, J. Fluorine Chem. 130 (2009) 609-614.
[39] S. Balalaie, F. Chadegani, F. Darviche, H.R. Bijanzadeh, Chin. J. Chem. 27 (2009) 1953-1956.
[40] D.-Q. Shi, S.-N. Ni, Y. Fang, J.-W. Shi, G.-L. Dou, X.-Y. Li, X.-S. Wang, J. Heterocycl. Chem. 45 (2008) 653-660.
[41] S. Rahmani, A. Amoozadeh, J. Nanostructures 4 (2014) 91-98.
[42] F. Rashedian, D. Saberi, K. Niknam, J. Chin. Chem. Soc. 57 (2010) 998-1006.
[43] M. Rahimifard, G. Mohammadi Ziarani, A. Badiei, S. Asadi, A. Abolhasani Soorki, Res. Chem. Intermed. 42 (2016) 3847-3861.
