Web of Science (Emerging Sources Citation Index)

Document Type: Original Research Article

Authors

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

2 Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, Iran

3 Chemistry Department, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

10.33945/SAMI/ECC.2019.2.1

Abstract

In this research work, a proficient method has been developed for the preparation of novel N-((2-chloroquinolin-3-yl) methylene)-4-methylbenzenamine derivatives from 2-chloroquinoline-3-carbaldehyde derivatives and p-toluidine in ethanol as solvent and using catalytic amount of acetic acid under reflux conditions to obtain desired products in good yields. The identification of all the synthesized compounds was confirmed by melting point, FT-IR, 1H NMR, and 13C NMR. Also, in present work all the synthesized compounds were evaluated for their molecular docking as anti-HIV-1 reverse transcriptase inhibitors using GOLD 5.2. software. The result of molecular docking showed that all the compounds established ‘π–π’ interactions with side chain of amino acid.

Graphical Abstract

Keywords

 
[1] S.K. Srivastava, P.M. Chauhan, A.P. Bhaduri, N. Fatima, R.K. Chatterjee, J. Med. Chem., 2000, 43, 2275-2279.
 
[2] N. Zhang, B. Wu, D. Powell, A. Wissner, M. B. Floyd, E. D. Kovacs, L. Toral-Barza, C. Kohler, Bioorg. Med. Chem. Lett., 2000, 10, 2825-2828.
 
[3] V.R. Solomon, H. Lee, Eur. J. Pharmacol., 2009, 625, 220-233.
 
[4] G. Roma, M. Di Braccio, G. Grossi, F. Mattioli, M. Ghia, Eur. J. Med. Chem., 2000, 35, 1021-1035.
 
[5] S. Bawa, S. Kumar, S. Drabu, R. Kumar, J. Pharm. Bioallied. Sci., 2010, 2, 64-71.
 
[6] A.K. Agarwal, T. Xu, M.R. Jacob, Q. Feng, M.C. Lorenz, L.A. Walker, A.M. Clark, Eukaryot. cell, 2008, 7, 387-400.
 
[7] W. Cunico, C.A. Cechinel, H.G. Bonacorso, M.A.P. Martins, N. Zanatta, M.V.N. de Souza, I.O. Freitas, R.P.P. Soares, A.U. Krettli, Bioorg. Med. Chem. Lett., 2006, 16, 649-653.
 
[8] Z. Arnold, Collect. Czech. Chem. Commun., 1959, 24, 4048-4049.
 
[9] O. Meth-Cohn, S.P. Stanforth, 1991.
 
[10] C.M. Marson, Tetrahedron, 1992, 48, 3659-3726.
 
[11] G. Jones, S.P. Stanforth, The Vilsmeier Reaction of Non-Aromatic Compounds, John Wiley & Sons, Inc., 2004.
 
[12] G. Jones, S.P. Stanforth, The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles, John Wiley & Sons, Inc., 2004.
 
[13] M.S. Newman, P.K. Sujeeth, J. Org. Chem., 1978, 43, 4367-4369.
 
[14] R.R. Amaresh, P.T. Perumal, Tetrahedron, 1998, 54, 14327-14340.
 
[15] M.L. Coté, M.J. Roth, Virus Res., 2008, 134, 186-202.
 
[16] H.C. Castro, N.I.V. Loureiro, M. Pujol-Luz, A.M.T. Souza, M.G. Albuquerque, D.O. Santos, L.M. Cabral, I.C. Frugulhetti, C.R. Rodrigues, Curr. Med. Chem., 2006, 13, 313-324.
 
[17] W. Reeve, V.C. Lowe, J. Chem. Educ., 1979, 56, 488.
 
[18] B.F. Abdel-Wahab, R.E. Khidre, J. Chem., 2013, 2013, 13.