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An eco-friendly water mediated synthesis of 1,2,3-triazolyl-2-aminopyrimidine hybrids as highly potent anti-bacterial agents

Sangaraiah Nagarajan ,  Poovan Shanmugavelan ,  Murugan Sathishkumar ,  Ramasamy Selvi ,  Alagusundaram Ponnuswamy ,  Hariharan Harikrishnan ,  Vellasamy Shanmugaiah

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Citation:  Sangaraiah Nagarajan, Poovan Shanmugavelan, Murugan Sathishkumar, Ramasamy Selvi, Alagusundaram Ponnuswamy, Hariharan Harikrishnan, Vellasamy Shanmugaiah. An eco-friendly water mediated synthesis of 1,2,3-triazolyl-2-aminopyrimidine hybrids as highly potent anti-bacterial agents[J]. Chinese Chemical Letters, 2014, 25(3): 419-422. doi: 10.1016/j.cclet.2013.12.017 shu

An eco-friendly water mediated synthesis of 1,2,3-triazolyl-2-aminopyrimidine hybrids as highly potent anti-bacterial agents

    • 通讯作者: Alagusundaram Ponnuswamy,
    Vellasamy Shanmugaiah,
摘要: An elegant and efficient synthesis of novel 1,2,3-triazole fused 2-aminopyrimidine hybrids has been accomplished for the first time in the green solvent viz. water. The hybrid molecules exhibit significant anti-bacterial activity when screened against three human pathogens viz. Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae. In comparison to the commercially marketed drug tetracycline, some of them are equally potent and a few are more potent.

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    1. [1] R.P. Mishra, E. Oviedo-Orta, P. Prachi, R. Rappuoli, F. Bagnoli, Vaccines and antibiotic resistance, Curr. Opin. Microbiol. 15 (2012) 596-602.[1] R.P. Mishra, E. Oviedo-Orta, P. Prachi, R. Rappuoli, F. Bagnoli, Vaccines and antibiotic resistance, Curr. Opin. Microbiol. 15 (2012) 596-602.

    2. [2] L.K. Siu, K.M. Yeh, J.C. Lin, C.P. Fung, F.Y. Chang, Klebsiella pneumoniae liver abscess: a new invasive syndrome, Lancet Infect. Dis. 12 (2012) 881-887.[2] L.K. Siu, K.M. Yeh, J.C. Lin, C.P. Fung, F.Y. Chang, Klebsiella pneumoniae liver abscess: a new invasive syndrome, Lancet Infect. Dis. 12 (2012) 881-887.

    3. [3] A.R. Marra, S.B. Wey, A. Castelo, et al., Nosocomial bloodstream infections caused by Klebsiella pneumoniae: impact of extended-spectrum beta-lactamase (ESBL) production on clinical outcome in a hospital with high ESBL prevalence, BMC Infect. Dis. 6 (2006) 24, http://dx.doi.org/10.1186/1471-2334-6-24.[3] A.R. Marra, S.B. Wey, A. Castelo, et al., Nosocomial bloodstream infections caused by Klebsiella pneumoniae: impact of extended-spectrum beta-lactamase (ESBL) production on clinical outcome in a hospital with high ESBL prevalence, BMC Infect. Dis. 6 (2006) 24, http://dx.doi.org/10.1186/1471-2334-6-24.

    4. [4] (a) H. Harikrishnan, A. Naif AbdullahI, K. Ponmurugan, R. Shyam Kumar, Nanocomposite using Saccharomyces cerevisiae and its antimicrobial activity against pathogens causing nosocomial, Chalcogenide Lett. 9 (2012) 509-515; (b) G.P. Bodey, R. Bolivar, V. Fainstein, L. Jadeja, Infections Caused by Pseudomonas aeruginosa, Rev. Infect. Dis. 5 (1983) 279-313.[4] (a) H. Harikrishnan, A. Naif AbdullahI, K. Ponmurugan, R. Shyam Kumar, Nanocomposite using Saccharomyces cerevisiae and its antimicrobial activity against pathogens causing nosocomial, Chalcogenide Lett. 9 (2012) 509-515; (b) G.P. Bodey, R. Bolivar, V. Fainstein, L. Jadeja, Infections Caused by Pseudomonas aeruginosa, Rev. Infect. Dis. 5 (1983) 279-313.

    5. [5] I. Chopra, M. Roberts, Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance, Microbiol. Mol. Biol. Rev. 65 (2001) 232-260.[5] I. Chopra, M. Roberts, Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance, Microbiol. Mol. Biol. Rev. 65 (2001) 232-260.

    6. [6] V. Yaziji, D. Rodríguez, H. Gutié rrez-de-Terán, et al., Pyrimidine derivatives as potent and selective A3 adenosine receptor antagonists, J. Med. Chem. 54 (2011) 457-471.[6] V. Yaziji, D. Rodríguez, H. Gutié rrez-de-Terán, et al., Pyrimidine derivatives as potent and selective A3 adenosine receptor antagonists, J. Med. Chem. 54 (2011) 457-471.

    7. [7] M.S. Mohamed, S.M. Awad, A.I. Sayed, Synthesis of certain pyrimidine derivatives as antimicrobial agents and anti-inflammatory agents, Molecules 15 (2010) 1882-1890.[7] M.S. Mohamed, S.M. Awad, A.I. Sayed, Synthesis of certain pyrimidine derivatives as antimicrobial agents and anti-inflammatory agents, Molecules 15 (2010) 1882-1890.

    8. [8] X. Chu, W. Depinto, D. Bartkovitz, et al., Discovery of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5-yl](2,3-difluoro-6-methoxyphenyl) methanone (R547) A potent and selective cyclin-dependent kinase inhibitor with significant in vivo antitumor activity, J. Med. Chem. 49 (2006) 6549-6560.[8] X. Chu, W. Depinto, D. Bartkovitz, et al., Discovery of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5-yl](2,3-difluoro-6-methoxyphenyl) methanone (R547) A potent and selective cyclin-dependent kinase inhibitor with significant in vivo antitumor activity, J. Med. Chem. 49 (2006) 6549-6560.

    9. [9] K.S. Atwal, G.C. Rovnyak, S.D. Kimball, et al., Dihydropyrimidine calcium channel blockers. Ⅱ. 3-Substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potentmimics of dihydropyridines, J.Med. Chem. 33 (1990) 2629-2635.[9] K.S. Atwal, G.C. Rovnyak, S.D. Kimball, et al., Dihydropyrimidine calcium channel blockers. Ⅱ. 3-Substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potentmimics of dihydropyridines, J.Med. Chem. 33 (1990) 2629-2635.

    10. [10] (a) N. Singh, S.K. Pandey, N. Anand, et al., Synthesis, molecular modeling and bioevaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents, Bioorg. Med. Chem. 21 (2011) 4404-4408; (b) Y.F. Zhao, Z.J. Liu, X. Zhai, et al., Synthesis and in vitro antitumor activity of novel diaryl urea derivatives, Chin. Chem. Lett. 24 (2013) 386-388.[10] (a) N. Singh, S.K. Pandey, N. Anand, et al., Synthesis, molecular modeling and bioevaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents, Bioorg. Med. Chem. 21 (2011) 4404-4408; (b) Y.F. Zhao, Z.J. Liu, X. Zhai, et al., Synthesis and in vitro antitumor activity of novel diaryl urea derivatives, Chin. Chem. Lett. 24 (2013) 386-388.

    11. [11] X.L. Wang, K. Wan, C.H. Zhou, Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities, Eur. J. Med. Chem. 45 (2010) 4631-4639.[11] X.L. Wang, K. Wan, C.H. Zhou, Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities, Eur. J. Med. Chem. 45 (2010) 4631-4639.

    12. [12] S.R. Wang, Q.L. Wang, Y. Wang, et al., Novel anthraquinone derivatives: synthesis via click chemistry approach and their induction of apoptosis in BGC gastric cancer cells via reactive oxygen species (ROS)-dependent mitochondrial pathway, Bioorg. Med. Chem. 18 (2008) 6505-6508.[12] S.R. Wang, Q.L. Wang, Y. Wang, et al., Novel anthraquinone derivatives: synthesis via click chemistry approach and their induction of apoptosis in BGC gastric cancer cells via reactive oxygen species (ROS)-dependent mitochondrial pathway, Bioorg. Med. Chem. 18 (2008) 6505-6508.

    13. [13] M. Whiting, J.C. Tripp, Y.C. Lin, et al., Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization, J. Med. Chem. 49 (2006) 7697-7710.[13] M. Whiting, J.C. Tripp, Y.C. Lin, et al., Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization, J. Med. Chem. 49 (2006) 7697-7710.

    14. [14] P. Pramitha, D. Bahulayan, Stereoselective synthesis of bio-hybrid amphiphiles of coumarin derivatives by Ugi-Mannich triazole randomization using copper catalyzed alkyne azide click chemistry, Bioorg. Med. Chem. Lett. 22 (2012) 2598-2603.[14] P. Pramitha, D. Bahulayan, Stereoselective synthesis of bio-hybrid amphiphiles of coumarin derivatives by Ugi-Mannich triazole randomization using copper catalyzed alkyne azide click chemistry, Bioorg. Med. Chem. Lett. 22 (2012) 2598-2603.

    15. [15] (a) M. Yu, S.S. Pochapsky, B.B. Snider, Synthesis of 7-epineoptilocaulin, mirabilin B, and isoptilocaulin. A unified biosynthetic proposal for the ptilocaulin and batzelladine alkaloids. Synthesis and structure revision of netamines E and G, J. Org. Chem. 73 (2008) 9065-9074; (b) A. Rahmati, Z. Khalesi, Catalyst free synthesis of fused pyrido[2,3-d]pyrimidines and pyrazolo[3,4-b]pyridines in water, Chin. Chem. Lett. 23 (2012) 1149-1152.[15] (a) M. Yu, S.S. Pochapsky, B.B. Snider, Synthesis of 7-epineoptilocaulin, mirabilin B, and isoptilocaulin. A unified biosynthetic proposal for the ptilocaulin and batzelladine alkaloids. Synthesis and structure revision of netamines E and G, J. Org. Chem. 73 (2008) 9065-9074; (b) A. Rahmati, Z. Khalesi, Catalyst free synthesis of fused pyrido[2,3-d]pyrimidines and pyrazolo[3,4-b]pyridines in water, Chin. Chem. Lett. 23 (2012) 1149-1152.

    16. [16] N. Sunduru, S. Nishi, P.M.S. Palne, S. Chauhan, Gupta Synthesis and antileishmanial activity of novel 2,4,6-trisubstituted pyrimidines and 1,3,5-triazines, Eur. J. Med. Chem. 44 (2009) 2473-2481.[16] N. Sunduru, S. Nishi, P.M.S. Palne, S. Chauhan, Gupta Synthesis and antileishmanial activity of novel 2,4,6-trisubstituted pyrimidines and 1,3,5-triazines, Eur. J. Med. Chem. 44 (2009) 2473-2481.

    17. [17] M. Meisenbach, T. Allmendinger, C.P. Mak, Scale-up of the synthesis of a pyrimidine derivative directly on solid support, Org. Process Res. Dev. 7 (2003) 553-558.[17] M. Meisenbach, T. Allmendinger, C.P. Mak, Scale-up of the synthesis of a pyrimidine derivative directly on solid support, Org. Process Res. Dev. 7 (2003) 553-558.

    18. [18] C.I. Herrerias, X.Q. Yao, Z.P. Li, C.J. Li, Reactions of C-H bonds in water, Chem. Rev. 107 (2007) 2546-2562.[18] C.I. Herrerias, X.Q. Yao, Z.P. Li, C.J. Li, Reactions of C-H bonds in water, Chem. Rev. 107 (2007) 2546-2562.

    19. [19] M. Sathishkumar, P. Shanmugavelan, S. Nagarajan, et al., Solvent-free protocol for amide bond formation via trapping of nascent phosphazenes with carboxylic acids, Tetrahedron Lett. 52 (2011) 2830-2833.[19] M. Sathishkumar, P. Shanmugavelan, S. Nagarajan, et al., Solvent-free protocol for amide bond formation via trapping of nascent phosphazenes with carboxylic acids, Tetrahedron Lett. 52 (2011) 2830-2833.

    20. [20] S. Nagarajan, P. Ran, P. Shanmugavelan, et al., The catalytic activity of titania nanostructures in the synthesis of amides under solvent-free conditions, New J. Chem. 36 (2012) 1312-1319.[20] S. Nagarajan, P. Ran, P. Shanmugavelan, et al., The catalytic activity of titania nanostructures in the synthesis of amides under solvent-free conditions, New J. Chem. 36 (2012) 1312-1319.

    21. [21] S. Nagarajan, P. Shanmugavelan, M. Sathishkumar, et al., Chemoselectivity in coupling of azides with thioacids in solution-phase and solvent-free conditions, Synth. Commun. 43 (2013) 37-41.[21] S. Nagarajan, P. Shanmugavelan, M. Sathishkumar, et al., Chemoselectivity in coupling of azides with thioacids in solution-phase and solvent-free conditions, Synth. Commun. 43 (2013) 37-41.

    22. [22] M. Sathishkumar, K. Palanikumar, A. Mariappan, S. Archana, A. Ponnuswamy, An environmentally benign solvent/catalyst-free one-pot synthesis of N-substituted phthalimides via Aza-wittig reaction, J. Iran. Chem. Soc. 9 (2012) 681-685.[22] M. Sathishkumar, K. Palanikumar, A. Mariappan, S. Archana, A. Ponnuswamy, An environmentally benign solvent/catalyst-free one-pot synthesis of N-substituted phthalimides via Aza-wittig reaction, J. Iran. Chem. Soc. 9 (2012) 681-685.

    23. [23] P. Shanmugavelan, S. Nagarajan, M. Sathishkumar, et al., Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis, Bioorg. Med. Chem. Lett. 21 (2011) 7273-7276.[23] P. Shanmugavelan, S. Nagarajan, M. Sathishkumar, et al., Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis, Bioorg. Med. Chem. Lett. 21 (2011) 7273-7276.

    24. [24] P. Shanmugavelan, M. Sathishkumar, S. Nagarajan, et al., The first solvent-free, microwave-accelerated, three-component synthesis of thiazolidin-4-ones via one-pot tandem Staudinger/aza-Wittig reaction, J. Heterocyclic. Chem. (1705), http://dx.doi.org/10.1002/jhet.[24] P. Shanmugavelan, M. Sathishkumar, S. Nagarajan, et al., The first solvent-free, microwave-accelerated, three-component synthesis of thiazolidin-4-ones via one-pot tandem Staudinger/aza-Wittig reaction, J. Heterocyclic. Chem. (1705), http://dx.doi.org/10.1002/jhet.

    25. [25] A. Ponnuswamy, P. Shanmugavelan, S. Nagarajan, M. Sathishkumar, The first onepot, solvent-free, microwave-accelerated, three-component synthesis of spirothiazolidin-4-ones via Staudinger/Aza-Wittig coupling/cyclization, Helv. Chim. Acta 95 (2012) 922-928.[25] A. Ponnuswamy, P. Shanmugavelan, S. Nagarajan, M. Sathishkumar, The first onepot, solvent-free, microwave-accelerated, three-component synthesis of spirothiazolidin-4-ones via Staudinger/Aza-Wittig coupling/cyclization, Helv. Chim. Acta 95 (2012) 922-928.

    26. [26] P. Shanmugavelan, M. Sathishkumar, S. Nagarajan, A. Ponnuswamy, A facile synthesis of 1,2,3-triazolyl indole hybrids via SbCl3-catalysed Michael addition of indoles to 1,2,3-triazolyl chalcones, J. Chem. Sci. 124 (2012) 941-950.[26] P. Shanmugavelan, M. Sathishkumar, S. Nagarajan, A. Ponnuswamy, A facile synthesis of 1,2,3-triazolyl indole hybrids via SbCl3-catalysed Michael addition of indoles to 1,2,3-triazolyl chalcones, J. Chem. Sci. 124 (2012) 941-950.

    27. [27] M. Sathishkumar, P. Shanmugavelan, S. Nagarajan, M. Dinesh, A. Ponnuswamy, Water promoted one pot three-component synthesis of tetrazoles, New J. Chem. 37 (2013) 488-493.[27] M. Sathishkumar, P. Shanmugavelan, S. Nagarajan, M. Dinesh, A. Ponnuswamy, Water promoted one pot three-component synthesis of tetrazoles, New J. Chem. 37 (2013) 488-493.

    28. [28] N. Sangaraiah, S. Murugan, S. Poovan, et al., Facile water promoted synthesis of 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids—highly potent antibacterial agents, Eur. J. Med. Chem. 58 (2012) 464-469.[28] N. Sangaraiah, S. Murugan, S. Poovan, et al., Facile water promoted synthesis of 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids—highly potent antibacterial agents, Eur. J. Med. Chem. 58 (2012) 464-469.

    29. [29] P. Shanmugavelan, S. Nagarajan, et al., An efficient and environmentally benign access towards synthesis of novel 1,2,3-triazolyl-pyrazoline hybrids, Lett. Org. Chem., in press.[29] P. Shanmugavelan, S. Nagarajan, et al., An efficient and environmentally benign access towards synthesis of novel 1,2,3-triazolyl-pyrazoline hybrids, Lett. Org. Chem., in press.

    30. [30] P. Shanmugavelan, M. Sathishkumar, S. Nagarajan, A. Ponnuswamy, An efficient and facile synthesis of novel 1,2,3-triazolyl-N-acylpyrazoline hybrids, Chin. Chem. Lett. 25 (2014) 146-148.[30] P. Shanmugavelan, M. Sathishkumar, S. Nagarajan, A. Ponnuswamy, An efficient and facile synthesis of novel 1,2,3-triazolyl-N-acylpyrazoline hybrids, Chin. Chem. Lett. 25 (2014) 146-148.

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  • 发布日期:  2013-12-24
  • 收稿日期:  2013-09-11
  • 网络出版日期:  2013-12-10
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