SFHS: Reusable catalyst for the synthesis of polyhydroquinoline derivatives and its molecular docking studies against tyrosine protein kinase
الموضوعات : Iranian Journal of Catalysis
Amit Waghmare
1
(Department of Chemistry, PVP College, Pravaranagar, Tal. Rahata-413 713)
Tushar Patil
2
(Department of Biotechnology,PVP College, Pravaranagar, Tal.Rahata-413 713)
Kailash Kadam
3
(Department of Chemistry, PVP College, Pravaranagar, Tal.Rahata-413 713)
Shivaji Pandit
4
(Department of Chemistry, PVP College, Pravaranagar, Tal.Rahata-413 713)
الکلمات المفتاحية: Multicomponent reaction, Polyhydroquinoline derivatives, Silica supported ferric hydrogen sulphate, Molecular docking,
ملخص المقالة :
An efficient synthesis of polyhydroquinoline derivatives is achieved via Hantzsch condensation reaction between aldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of catalytic amount of SFHS in ethanol. This method gives remarkable advantages such as shorter reaction time, simple workup procedure and good to excellent yields. Furthermore the catalyst can be recovered conveniently and reused efficiently. To analyze potential anticancer activity, synthesized derivatives were docked to tyrosine protein kinase (1YJ) against 4ST and PTR binding sites.
[1] (a) A. Distilo, S. Visentin, C. Clara, A.M. Gasco, G. Ermondi, Gasco, J. Med. Chem. 41 (1998) 5393-5401. (b) Y. Sawada, H. Kayakiri, Y. Abe, T. Mizutani, N. Inamura, M. Asano, C. Hatori, I. Arsmori, T. Oku, H. Tanaka, J. Med. Chem. 47 (2004) 2853-2863. (c) R. Shan, C. Velazquez, E.E. Knaus, J. Med. Chem. 47 (2004) 254-261. (d) M. Suarez, Y. Verdecia, B. Illescas, Z. Martinez-Alvarez, A. Alvarez, E. Ochoa, C. Seoane, N. Kayali, N. Martin, Tetrahedron. 59 (2003) 9179-9186.
[2] (a) T. Godfraid, R. Miller, M. Wibo, Pharmacol. Rev. 38 (1986) 321-416. (b) A. Sausins, G. Duburs, Heterocycles 27 (1988) 269-289.
[3] R. Mannhold, B. Jablonka, W. Voigdt, K. Schoenafinger, K. Schravan, Eur. J. Med. Chem. 27 (1992) 229-235.
[4] A. Kumar, S. Sharma, V.D. Tripathi, R.A. Maurya, S.P. Shrivastava, G. Bhatia, A.K. Tamrakar, A.K. Srivastava, Bioorg. Med. Chem. 18 (2010) 4138-4148.
[5] (a) G. Grun, A. Fleckenstein, A. Forsch. Drug Res. 22 (1972) 334-344.
(b) F. Bossert, H. Meyer, E. Wehinger, Angew. Chem. 93 (1981) 755-763. (c) R.A. Janis, D.J. Triggle, J. Med. Chem. 26 (1983) 775-785.
[6] Y.M. Chang, H.J. Kung, C.P. Evans, Neoplasia. 9 (2007) 90-100.
[7] (a) B. Love, K.M. Snader, J. Org. Chem. 30 (1965) 1914-1916. (b) M. Suarez, E. Ochoa, Y. Verdecia, B. Pita, L. Moran, N. Martin, M. Quinteiro, C. Seoane, J. Soto, H. Novoa, N. Blaton, O.M. Peters, Tetrahedron. 55 (1999) 875-884.
[8] (a) S. Ko, M.N.V. Sastry, C. Lin, C.F. Yao, Tetrahedron Lett. 46 (2005) 5771-5774. (b) F.M. Moghaddam, H. Saeidian, Z. Mirjafary, A. Sadeghi, J. Iran. Chem. Soc. 6 (2009) 317-324.
[9] M. Maheswaara, V. Siddaiah, G.L.V. Damu, C.V. Rao, Arkivoc. ii (2006) 201-206.
[10] G. Sabitha, G.S.K.K. Reddy, C.S. Reddy, J.S. Yadav, Tetrahedron Lett. 44 (2003) 4129-4131.
[11] S.R. Cherkupally, R. Mekala, Chem. Pharm. Bull. 56 (2008) 1002-1004.
[12] A. Kumar, R. Maurya, Tetrahedron Lett. 48 (2007) 3887-3890.
[13] S. Ko, C.F. Yao, Tetrahedron. 62 (2006) 7293-7299.
[14] C.S. Reddy, M. Raghu, Ind. J. Chem. 47B (2008) 1578-1582.
[15] N.N. Karade, V.H. Budhewar, S.V. Shinde, W.N. Jadhav, Lett. Org. Chem. 4 (2007) 16-24.
[16] L.S. Gadekar, S.S. Katkar, S.R. Mane, B.R. Arbad, M.K. Lande, Bull. Korean Chem. Soc. 30 (2009) 2532-2534.
[17] (a) L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z.Y. Fan, H. Tian, C.T. Qian, Tetrahedron. 61 (2005) 1539-1543. (b) J.L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Cat. A: Chem. 256 (2006) 309-311.
[18] A.R. Supale, G.S. Gokavi, Open Catal. J. 2 (2009) 61-65.
[19] G. Song, B. Wang, X. Wu, Y. Kang, L. Yang, Synth. Commun. 35 (2005) 2875-2880.
[20] J.P. Nirmal, P.V. Dadhaniya, M.P. Patel, R.G. Patel, Ind. J. Chem. 49B (2010) 587-592.
[21] (a) M.M. Heravi, K. Bakhtiari, N.M. Javedi, F.F. Bamoharram, M. Saeedi, H.A. Oskooie, J. Mol. Cat. A: Chem. 264 (2007) 50-52. (b) M. M. Heravi, K. Bakhtiari, V. Zadsirjan, M. Saeedi, F.F. Bamoharram, Iran J. Org. Chem. 2 (2010) 298-302.
[22] E. Mosaddegh, A. Hassankhani, Bull. Chem. Soc. Ethiop. 26 (2012) 461-465.
[23] A. Kumar, R.A. Maurya, Tetrahedron 63 (2007) 1946-1952.
[24] (a) L. Saikia, D. Dutta, D.K. Dutta, Catal. Commun. 19 (2012) 1-4. (b) S.M. Vahdat, F. Chekin, M. Hatami, M. Khavarpour, S. Baghery, Z. Roshan-Kouhi, Chin. J. Catal. 34 (2013) 758-763. (c) S.B. Apkal, K.F. Shelke, B.B. Shingaten, M. S. Shingare, Tetrahedron Lett. 50 (2009) 1754-1756.
[25] P. Salehi, M.M. Khodaei, M.A. Zolfigol, S. Zeinoldini, Synth. Commun. 33 (2003) 1367-1373.
[26] H. Eshghi, M. Rahimizadeh, S. Saberi, Catal. Commun. 9 (2008) 2460-2466.
[27] H.R. Shaterian, H. Yarahmadi, M. Ghashang, Arkivoc xvi (2007) 298-313.
[28] H.R. Shaterian, M. Ghashang, J. Braz. Chem. Soc. 19 (2008) 1053-1058.
[29] (a) H. Eshghi, J. Chin. Chem. Soc. 53 (2006) 987-990. (b) H. Eshghi, M. Bakavoli, H. Moradi, Chin. Chem. Lett. 20 (2009) 663-667.