Document Type: Original Research Article

Authors

1 Payame Noor University of Abhar

2 Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran

3 Department of Biology, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran

Abstract

This work described a simple and efficient method for the synthesis of 1-azabicyclo[3.1.0]hexane-3-ene derivatives. arylidenmalononitriles and hydroxylamine hydrochloride in the presence of NaOH, under microwave irradiation and solvent-free conditions produced the titled compounds in good to excellent yields. Using of simple chemicals, short reaction times, and solvent-free conditions, high yields of products, high atomic economy , and eco-friendly are the important advantages of this method. The antibacterial effect of 4-amino-2,6-bis(2,4-dichlorophenyl)-1-azabicyclo[3.1.0]hex-3-ene-3,5-dicarbonitrile was evaluated by minimum inhibitory concentration and disk diffusion method against the standard strains of Staphylococcus aureus and Pseudomonas aeruginosa. Minimum inhibitory concentrations of 2h were 40 and 30 mg/ml for P. aeruginosa and S. aureus respectively and the maximum inhibitory zones were 4 and 5 mm on average, respectively.

Graphical Abstract

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Main Subjects

[1] S.-X. Zhai, H.-R. Dong, Z.-B. Chen, Y.-M. Hu, H.-S. Dong, Tetrahedron, 201470, 8405-8412.

[2] H. Clavier, H. Pellissier, Adv. Synth. Catal., 2012354, 3347-3403.

[3] H. Pellissier, Adv. Synth. Catal., 2012354, 237-294.

[4] C.A. Ray, E. Risberg, P. Somfai, Tetrahedron Lett., 200142, 9289-9291.

[5] C.A. Ray, E. Risberg, P. Somfai, Tetrahedron, 200258, 5983-5987.

[6] D. Pufky-Heinrich, M. Ciesielski, L. Gharnati, O. Walter, M. Doering, Heterocycles, 201081, 1811-1825.

[7] K. Banert, F. Köhler, A. Melzer, I. Scharf, G. Rheinwald, T. Rüffer, H. Lang, R. Herges, K. Heß, N. Ghavtadze, Chem. - Eur. J., 201117, 10071-10080.

[8] M.J. Alves, J.F. Bickley, T.L. Gilchrist, J. Chem. Soc., Perkin Trans., 199911, 1399-1402.

[9] S. Carlsson, S. Olesen, S. Lawesson, Nouv. J. Chim.- New J. Chem., 19804, 269-271.

[10] M.A. Graham, A.H. Wadsworth, M. Thornton-Pett, C.M. Rayner, Chem. Commun.2001, 966-967.

[11] R.E. Banks, M.K. Besheesh, N.J. Lawrence, R.G. Pritchard, D.J. Tovell, Chem. Commun., 1999, 47-48.

[12] M. Ashtary, A. Ramazani, A. Kazemizadeh, N. Shajari, N. Fattahi, S.W. Joo, Phosphorus, Sulfur Silicon Relat. Elem.2016191, 1402-1407.

[13] M. Bahrami, A. Ramazani, Y. Hanifehpour, N. Fattahi, S. Taghavi Fardood, P. Azimzadeh Asiabi, S.W. Joo, Phosphorus, Sulfur Silicon Relat. Elem., 2016191, 1368-1374.

[14] A. Jafari, A. Ramazani, H. Ahankar, P.A. Asiabi, F. Sadri, S.W. Joo, Phosphorus, Sulfur Silicon Relat. Elem.2016191, 373-380.

[15] A. Ramazani, Y. Ahmadi, H. Aghahosseini, S.W. Joo, Phosphorus, Sulfur Silicon Relat. Elem.2016191, 354-358.

[16] A. Ramazani, Y. Ahmadi, M. Rouhani, N. Shajari, A. Souldozi, Heteroat. Chem., 201021, 368-372.

[17] A. Ramazani, Y. Ahmadi, R. Tarasi, Heteroat. Chem., 201122, 79-84.

[18] A. Ramazani, N. Shajari, A. Mahyari, Y. Ahmadi, Mol. Diversity201115,  521-527.

[19] A. Ramazani, Y. Ahmadi, A.M. Malekzadeh, A. Rezaei, Heteroat. Chem., 201122, 692-698.

[20] F.Z. Nasrabadi, A. Ramazani, Y. Ahmadi, Mol. Diversity201115, 791-798.

[21] A. Ramazani, Y. Ahmadi, Z. Karimi, A. Rezaei, J. Heterocycl. Chem., 201249, 1447-1451.

[22] A. Ramazani, F.Z. Nasrabadi, Z. Karimi, M. Rouhani, Synth. Commun., 201343, 1818-1830.

[23] M. Rouhani, A. Ramazani, S.W. Joo, Ultrason. Sonochem., 201421,  262-267.

[24] M. Rouhani, A. Ramazani, S.W. Joo, Ultrason. Sonochem., 201522,  391-396.

[25] H. Ahankar, A. Ramazani, I. Amini, Y. Ahmadi, A. Souldozi, Heteroat. Chem., 201122, 612-616.

[26] A. Ramazani, Y. Ahmadi, A. Mahyari, Synth. Commun., 201141, 2273-2282.

[27] A. Ramazani, F.Z. Nasrabadi, A.M. Malekzadeh, Y. Ahmadi, Monatsh. Chem., 2011142, 625-630.

[28] A. Ramazani, M. Khoobi, A. Torkaman, F.Z. Nasrabadi, H. Forootanfar, M. Shakibaie, M. Jafari, A. Ameri, S. Emami, M.A. Faramarzi, Eur. J. Med. Chem., 201478, 151-156.

[29] H. Javanbani, A. Ramazani, S.W. Joo, Y. Ahmadi, V. Azizkhani, P. Azimzadeh Asiabi, Iran. Chem. Commun., 20153,  310-322.

[30] A. Ramazani, F. Kalantari, F. Zeinali Nasrabadi, Iran. Chem. Commun., 20164,  155-164.

[31] A. Ramazani, A. Jafari, S.W. Joo, Y. Ahmadi, F. Sadri, P. Azimzadeh Asiabi, Iran. Chem. Commun., 20164, 42-56.

[32] V. Azizkhani, A. Ramazani, S. Woo Joo, Iran. Chem. Commun., 20153, 146-158.

[33] K.A. Tehrani, K. Van Syngel, M. Boelens, J. Contreras, N. De Kimpe, D.W. Knight, Tetrahedron Lett., 200041, 2507-2510.

[34] B.A. Trofimov, E.Y. Schmidt, I.M. Al’bina, I.A. Ushakov, N.I. Protsuk, E.Y. Senotrusova, O.N. Kazheva, G.G. Aleksandrov, O.A. Dyachenko, Tetrahedron Lett., 200950, 3314-3317.

[35] A. Kamaraj, R. Rajkumar, K. Krishnasamy, J. Mol. Struct., 2015, 1088, 179-189.

[36] H. Kiyani, F. Albooyeh, S. Fallahnezhad, J. Mol. Struct., 20151091, 163-169.

[37] M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron200460, 11743-11749.

[38] M. Ghorbani, B. Mohammadi, M. Saraii, B. Masoumi, M. Abbasian, A. Ramazani, K. Slepokura, T. Lis, Org. Lett., 201618, 4759-4761.

[39] A. Pacheco, A. Alcântara, G. Corrêa, V. Abreu, Relationships between chemical structure and activity of triterpenes against gram-positive and gram-negative bacteria, INTECH Open Access Publisher, 2012.

[40] R. Wise, T. Hart, O. Cars, M. Streulens, R. Helmuth, P. Huovinen, M. Sprenger, Br. Med. J., 1998317, 609-611.

[41] A. Tsakris, S. Pournaras, N. Woodford, M.-F.I. Palepou, G.S. Babini, J. Douboyas, D.M. Livermore, J. Clin. Microbiol., 200038, 1290-1292.

[42] A. Pantosti, A. Sanchini, M. Monaco, Future Microbiol., 20072, 323-334.

[43] S. Zorofchian Moghadamtousi, H. Abdul Kadir, P. Hassandarvish, H. Tajik, S. Abubakar, K. Zandi, A BioMed Res. Int., 2014, 2014.

[44] B. Mohammadi, M. Shafieey, H. Kazemi, A. Ramazani, Chin. Chem. Lett., 2013, 24, 497-499.

[45] B. Mohammadi, M. Adib, Chin. Chem. Lett., 2014, 25, 553-556.

[46] B. Mohammadi, Monatsh. Chem., 2016, 147, 1939-1943.

[47] B. Mohammadi, H. Kazemi, M. Shafieey, Monatsh. Chem., 2014, 145, 1649-1652.

 

[48] B. Mohammadi, M. Shafieey, H. Kazemi, Iran. Chem. Commun., 2015, 3, 302-309.

[49] B. Mohammadi, M. Rahmani, Iran. Chem. Commun., 2016, 4, 226-235.

[50] M. Aramendia, V. Borau, C. Jimenez, J. Marinas, F. Romero, React. Kinet. Catal. Lett., 200069, 311-316.

[51] A. Hindler, J. Jorgensen, Procedures in antimicrobial susceptibility testing, MAHON, CR & MANUSELIS Jr., G. Textbook of diagnostic Microbiology. Philadelphia, WB Saunders, 1995, 63-64.