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Abstract
A series of piperidine-4-carboxylic acid methyl ester coupled with N-phthaloyl amino acids derivatives were synthesized, characterized and their antimicrobial properties were evaluated. These compounds were synthesized with dicyclohexylcarbodimide coupling of piperidine-4-carboxylic acid methyl ester with N-phthaloyl amino acids with N, N'-dicyclohexylcarbodiimide followed by ring opening reaction with cyclopropylamine and reaction of ester with hydrazine hydrate to obtain final compound characterized using IR, 1H and 13C-NMR and mass spectroscopy. The synthesized compounds were screened for their in vitro antimicrobial activity against S. aurous, E. coli, P. aeruginosa, S. typhimurium, F. oxysporum and A. alternate. Some of these compounds exhibited moderate to good activity, where as some were inactive.
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References
- [1]. S.Pande P. Utale ,Gholse S, Tekade P and Gunjate J, An efficient Synthesis of Trisubstituted Purine via Unusual coupling of N-Phthaloyl Derivatives of Amino Acids, International Journal of ChemTech Research, 5(6), 2013, 3023-31.
- [2]. X. He, A. Alian, R. Stroud, and P. R. Ortiz de Montellano, J. Med. Chem., 49(21), 2006, 6308 – 6323.
- [3]. F. Schiaffella, R. Fringuelli, V. Cecchetti, et al., Farmaco, 44(11), 1989, 1031 – 1044.
- [4]. C. Dittrich, V. Dieras, P. Kerbrat, et al., Investig. New Drugs: J.New Anticancer Agents, 21(3), 2003, 347–352.
- [5]. G. M. Keating, A. Santoro, Drugs, 69(2), 2009, 223 – 240.
- [6]. F. J. Torriani, M. Rodriguez-Torres, J. K. Rockstroh, et al., New Engl. J. Med., 351(5), 2004, 438 – 450.
- [7]. Y. K. Jong, J. S. Hee, H. L. Sung, et al., Bioorg. Med. Chem.Lett., 19(1), 2009, 142 –145.
- [8]. S. Sidique, R. Ardecky, Y. Su, et al., Bioorg. Med. Chem. Lett., 19 (1), 2009, 222 – 225.
- [9]. A. C. Leite, K. P. da Silva, I. A. de Souza, et al., Eur. J. Med. Chem., 39(12), 2004, 1059 – 1065.
- [10]. X. Collin, J. Robert, G. Wielgosz, et al., Eur. J. Med. Chem., 36 (7–8), 2001, 639–649.
- [11]. A. A. Abdel-Aziz, Eur. J. Med. Chem., 42(5), 2007, 614 – 626.
- [12]. CK.Belwal and Joshi KA, Pharmacological examination and synthesis of some Schiff bases and thiazolidinone derivatives of 5-amino-1H-imidazole-4-carboxamide, Der Pharma Chemica, 4(5), 2012, 1873-78.
- [13]. E. Moreno, S. Ancizu, S. Perez-Silanes, et al., Eur. J. Med. Chem., 45(10), 2010, 4418 – 4426.
- [14]. M. Ohkubo, A. Kuno, H. Sakai, and H. Takasugi, Chem. Pharm. Bull, 43(6), 1995, 947 – 954.
- [15]. Jigisha A. Modi, (2012), Design, synthesis of some 2, 6, 9- trisubstituted purinyl thioureido derivatives and evaluation of antimicrobial activity, Med Chem. Res 1660-1664.
References
[1]. S.Pande P. Utale ,Gholse S, Tekade P and Gunjate J, An efficient Synthesis of Trisubstituted Purine via Unusual coupling of N-Phthaloyl Derivatives of Amino Acids, International Journal of ChemTech Research, 5(6), 2013, 3023-31.
[2]. X. He, A. Alian, R. Stroud, and P. R. Ortiz de Montellano, J. Med. Chem., 49(21), 2006, 6308 – 6323.
[3]. F. Schiaffella, R. Fringuelli, V. Cecchetti, et al., Farmaco, 44(11), 1989, 1031 – 1044.
[4]. C. Dittrich, V. Dieras, P. Kerbrat, et al., Investig. New Drugs: J.New Anticancer Agents, 21(3), 2003, 347–352.
[5]. G. M. Keating, A. Santoro, Drugs, 69(2), 2009, 223 – 240.
[6]. F. J. Torriani, M. Rodriguez-Torres, J. K. Rockstroh, et al., New Engl. J. Med., 351(5), 2004, 438 – 450.
[7]. Y. K. Jong, J. S. Hee, H. L. Sung, et al., Bioorg. Med. Chem.Lett., 19(1), 2009, 142 –145.
[8]. S. Sidique, R. Ardecky, Y. Su, et al., Bioorg. Med. Chem. Lett., 19 (1), 2009, 222 – 225.
[9]. A. C. Leite, K. P. da Silva, I. A. de Souza, et al., Eur. J. Med. Chem., 39(12), 2004, 1059 – 1065.
[10]. X. Collin, J. Robert, G. Wielgosz, et al., Eur. J. Med. Chem., 36 (7–8), 2001, 639–649.
[11]. A. A. Abdel-Aziz, Eur. J. Med. Chem., 42(5), 2007, 614 – 626.
[12]. CK.Belwal and Joshi KA, Pharmacological examination and synthesis of some Schiff bases and thiazolidinone derivatives of 5-amino-1H-imidazole-4-carboxamide, Der Pharma Chemica, 4(5), 2012, 1873-78.
[13]. E. Moreno, S. Ancizu, S. Perez-Silanes, et al., Eur. J. Med. Chem., 45(10), 2010, 4418 – 4426.
[14]. M. Ohkubo, A. Kuno, H. Sakai, and H. Takasugi, Chem. Pharm. Bull, 43(6), 1995, 947 – 954.
[15]. Jigisha A. Modi, (2012), Design, synthesis of some 2, 6, 9- trisubstituted purinyl thioureido derivatives and evaluation of antimicrobial activity, Med Chem. Res 1660-1664.