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http://dx.doi.org/10.5012/jkcs.2013.57.4.455

Synthesis and Biological Evaluation of 2-Amino-4H-pyran-3,4,5-tricarboxylate Salt Derivatives  

Akbari, Ali (Department of Chemistry, Faculty of Science, University of Jiroft)
Azami-Sardooei, Zabihollah (Department of Corp Protection, Faculty of Agriculture, University of Jirof)
Hosseini-Nia, Asghar (Department of Plant Protection National Research Station of Ornamental Plants)
Publication Information
Journal of the Korean Chemical Society / v.57, no.4, 2013 , pp. 455-460 More about this Journal
Abstract
A novel and simple method for the synthesis of 2-amino-4H-pyran-3,4,5-tricarboxylate derivative and the evaluation of their antibacterial activity against Pseudomonas syringae, Xanthomonas citi and Pectobacterium carotovorum are reported. The structure of the isolated compounds has been determined by means of $^1H/^{13}C$ NMR and FT-IR Spectroscopy. The reaction of alkyl isocyanides with acetylenic esters in the presence of dimethyl acetone-1,3-dicarboxylate in the present of $BF_3.SiO_2$ at ambient temperature. Some of the compound showed significant inhibition to growth of bacteria.
Keywords
Biological evaluation; Antibacterial activity; 4H-Pyran-3; 4; 5-tricarboxylate; $BF_3.SiO_2$;
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1 Ivanovic, Z.; Zivkovic, S.; Starovic, M.; Josic, D.; Stankovic, S.; Gavrilovic, V. Arch. Biol. Sci. 2009, 61(4), 863.   DOI
2 Rodrigo, J. Sci. Hortic. 2000, 85(3), 155.   DOI   ScienceOn
3 Lemriss, S.; Marquet, B.; Ginestet, H.; Lefeuvre, L.; Fassouane, A.; Boiron, P. J. Mycol. Med. 2003, 13, 189.
4 Wilson, K.; Clark, J. H. Synthesis of a Novel Supported Solid Acid $BF_{3}$ Catalyst. Chem. Commun. 1998, 2135.
5 Klapotke, T. M.; Mc Monagle, F.; Spence, R. R.; Winfield, J. M. $\gamma$-Alumina-Supported Boron Trifluoride: Catalysis, Radiotracer Studies and Computations. J. Fluorine. Chem. 2006, 127, 1446.   DOI   ScienceOn
6 Sadegi, B.; Mirjalili, B. F.; Hashemi, M. M. $BF_{3}{\cdot}SiO_{2}$: An Efficient Reagent System for the One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles. Tetrahedron Lett. 2008, 49, 2575.   DOI   ScienceOn
7 Mirjalili, B. F.; Bamoniri, A.; Akbari, A. $BF_{3}{\cdot}SiO_{2}$: An Efficient Alternative for the Synthesis of 14-Aryl or Alkyl-14H-dibenzo[a,j]xanthenes. Tetrahedron Lett. 2008, 49, 6454.   DOI   ScienceOn
8 Boodhoo, K. V. K.; Dunk, W. A. E.; Vicevic, M.; Jachuck, R. J.; Sage, V.; Macquarrie, D. J.; Clark, J. H. Classical Cationic Polymerisation of Styrene in a Spinning Disc Reactor Using Silica Supported $BF_{3$ Catalyst. J. Appl. Polym. Sci. 2006, 101(1), 8.   DOI   ScienceOn
9 Dindulkar, S. D.; Parthiban P.; Y. T. Jeong. $BF_{3}{\cdot}SiO_{2}$ is a Simple and Efficient Lewis Acid Catalyst for the One-Pot Synthesis of Polyfunctionalized Piperidin-4-ones. Monatsh. Chem. 2012, 143, 113.   DOI
10 Reddy, M. V.; Dindulkar, S. D.; Jeong, Y. T. $BF_{3}{\cdot}SiO_{2}$- Catalyzed One-Pot Synthesis of $\alpha$-Aminophosphonates in Ionic Liquid and Neat Conditions. Tetrahedron Lett. 2011, 52, 4764.   DOI   ScienceOn
11 Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. Biorg. Med. Chem. Lett. 2000, 10, 835.   DOI   ScienceOn
12 Sadegi, B.; Mirjalili, B. F.; Hashememi, M. M. $BF_{3}{\cdot}SiO_{2}$: An Efficient Heterogeneous Alternative for Regio-Chemo and Stereoselective Claisen-schmidt Condensation. J. Iran. Chem. Soc. 2008, 5(4), 694.   DOI   ScienceOn
13 Mirjalili, B. F.; Bamoniri, A.; Akbari, A. One-pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (thiones) Promoted by Nano-$BF_{3}{\cdot}SiO_{2}$. J. Iran. Chem. Soc. 2011, 8, 135.   DOI
14 Rahman, A.; Choudhary, M. I.; Thomsen, W. J. Bioassay Techniques for Drug Development; Harwood Academic Publishers: Amsterdam, 2001; p 14.
15 Mirjalili, B. F.; Bamoniri, A.; Akbari, A. Nano-$BF_{3}{\cdot}SiO_{2}$: a Reusable and Eco-friendly Catalyst for Synthesis of Quinoxalines. Chem. Heterocycl. Comp. 2011, 47(4), 487.   DOI
16 Rho, H. S.; Baek, H. S.; You, J. W.; Kim, S.; Lee, J. Y.; Kim, D. H.; Chang, I. S. Bull. Korean Chem. Soc. 2007, 28(3), 471.   DOI   ScienceOn
17 Li, D.-H.; Cai, S.-X.; Tian, L.; Lin, Z.-J.; Zhu, T.-J.; Fang, Y.-C.; Liu, P.-P.; Gu, Q.-Q.; Zhu, W.-M. Arch. Pharm. Res. 2007, 30(9), 1051.   DOI   ScienceOn
18 Wang, T.-S.; Wang, S.-Q.; Xiao, D.-L. J. Med. Plants Res. 2012, 6(26), 4259.
19 Groweiss, A.; Cardellins, J. H.; Boyd, M. R. J. Nat. Prod. 2000, 63, 1537.   DOI   ScienceOn
20 Deng, Y.; Lee, J. P.; Ramamonjy, M. T.; Synder, J. K.; Des Etages, S. A.; Kanada, D.; Synder, M. P.; Turner, C. J. J. Nat. Prod. 2000, 63, 1082.   DOI   ScienceOn
21 Nasiri, F.; Nazem, F.; Pourdavaie, K. Mol. Divers. 2007, 11, 101.   DOI
22 Khan, I. A.; Avery, M. A.; Burandt, C. L.; Goins, D. K.; Mikell, J. R.; Nash, T. E.; Azadega, A.; Walker, L. A. J. Nat. Prod. 2000, 63, 1414.   DOI   ScienceOn
23 Mori, K.; Audran, G.; Monti, H. Synlett 1998, 259.
24 Pietta, P. J. J. Nat. Prod. 2000, 63, 1035.   DOI   ScienceOn
25 Park, E.-J.; Gray, P. M.; Oh, S.-W.; Kronenberg, J.; Kang, D.-H. J. Food. Science. 2008, 73(6), M278.   DOI
26 Toth, I. K.; Bell, K. S.; Holeva, M. C., Birch, P. R. J. Molecular Plant Pathology 2003, 4(1), 17.   DOI   ScienceOn
27 Yang, J. W.; Yi, H.-S.; Kim, H.; Lee, B.; Lee, S.; Ghim, S.-Y.; Ryu, C.-M. J. Ecology. 2011, 99(1), 46.   DOI   ScienceOn
28 Boch, J.; Bonas, U. Annual Review of Phytopathology 2010, 48, 419.   DOI   ScienceOn