Synthesis and Evaluation of 2-Amino-4H-Pyran-3-Carbonitrile Derivatives as Antitubercular Agents

Abstract

A series of 2-amino-4H-pyran-3-carbonitrile derivatives were designed and synthesized. Their antitubercular activities
were evaluated against autoluminescent M. tuberculosis H37Ra and standard strain M. tuberculosis H37Rv. No obvious
antitubercular activities could be observed (MIC > 10 ug/mL). The results are in sharp contrast with the previously reported
data.

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C. Chen, M. Lu, Z. Liu, J. Wan, Z. Tu, T. Zhang and M. Yan, "Synthesis and Evaluation of 2-Amino-4H-Pyran-3-Carbonitrile Derivatives as Antitubercular Agents," Open Journal of Medicinal Chemistry, Vol. 3 No. 4, 2013, pp. 128-135. doi: 10.4236/ojmc.2013.34015.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] World Health Organization, “Global Tuberculosis Control Report 2013,” World Health Organization, Geneva. http://www.who.int/tb/publications/global_report/en/
[2] L. Christian, G. Philippe, U. Mukund, L. Knut, G. Haileyesus and R. Mario, “Global Tuberculosis Control: Lessons Learnt and Future Prospects,” Nature Reviews Microbiology, Vol. 10, No. 6, 2012, pp. 407-416. http://dx.doi.org/10.1038/nrmicro2797
[3] World Health Organization, “Multidrug-Resistant Tuberculosis (MDR-TB),” World Health Organization, Geneva. http://www.who.int/tb/challenges/mdr/en/index.html
[4] M. P. Grobusch, “Drug-Resistant and Extensively Drug-Resistant Tuberculosis in Southern Africa,” Current Opinion in Pulmonary Medicine, Vol. 16, No. 3, 2010, pp. 180-185. http://dx.doi.org/10.1097/MCP.0b013e3283378680
[5] J. L. Mainardi, J. E. Hugonnet, L. Gutmann and M. Arthur, “Fighting Resistant Tuberculosis with Old Compounds: The Carbapenem Paradigm,” Clinical Microbiology and Infection, Vol. 17, No. 12, 2011, pp. 1755-1756. http://dx.doi.org/10.1111/j.1469-0691.2011.03699.x
[6] A. G. Nikalje and P. Mudassar, “Multidrug-Resistant Mycobacterium Tuberculosis: A Brief Review,” Asian Journal of Biological Sciences, Vol. 4, No. 2, 2011, pp. 101-115. http://dx.doi.org/10.3923/ajbs.2011.101.115
[7] R. Shi and I. Sugawara, “Development of New Anti-Tuberculosis Drug Candidates,” Tohoku Journal of Experimental Medicine, Vol. 221, No. 2, 2010, pp. 97-106. http://dx.doi.org/10.1620/tjem.221.97
[8] S. T. Cole and G. Riccardi, “New Tuberculosis Drugs on the Horizon,” Current Opinion in Microbiology, Vol. 14, No. 5, 2011, pp. 570-576.
[9] R. R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari and D. Sriram, “An Atomefficient, Solvent-Free, Green Synthesis and Antimycobacterial evaluation of 2-amino-6- Methyl-4-Aryl-8-[(E)-Arylmethylidene]-5,6,7,8-Tetrahy-Dro-4H-Pyrano[3,2-c]Pyridine-3-Carbonitriles,” Bioorganic & Medicinal Chemistry Letters, Vol. 17, No. 23, 2007, pp. 6459-6462. http://dx.doi.org/10.1016/j.bmcl.2007.09.095
[10] R. R. Kumar, S. Perumal, J. C. Menendez, P. Yogeeswari and D. Sriram, “Antimycobacterial Activity of Novel 1,2,4- Oxadiazole-Pyranopyridine/Chromene Hybrids Generated by Chemoselective 1,3-Dipolar Cycloadditions of Nitrile Oxides,” Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 11, 2011, pp. 3444-3450. http://dx.doi.org/10.1016/j.bmc.2011.04.033
[11] Z. P. Hu, C. L. Lou, J. J. Wang, C. X. Chen and M. Yan, “Organocatalytic Conjugate Addition of Malononitrile to Conformationally Restricted Dienones,” The Journal of Organic Chemistry, Vol. 76, No. 10, 2011, pp. 3797- 3804.
[12] Z. P. Hu, W. J. Wang, X. G. Yin, X. J. Zhang and M. Yan, “Enantioselective Synthesis of 2-Amino-4H-Pyrans via the Organocatalytic Cascade Reaction of Malononitrile and A-Substituted Chalcones,” Tetrahedron: Asymmetry, Vol. 23, No. 22-23, 2012, pp. 461-467.
[13] H. F. Wang, P. Li, H. F. Cui, X. W. Wang, J. K. Zhang, W. Liu and G. Zhao, “Highly Enantioselective Synthesis of A-Trichloromethyldihydropyrans Catalyzed by Bifunctional Organocatalysts,” Tetrahedron, Vol. 67, No. 10, 2011, pp. 1774-1780. http://dx.doi.org/10.1016/j.tet.2011.01.043
[14] T. Y. Zhang, S. Y. Li and E. L. Nuermberger, “Autolu-minescent Mycobacterium Tuberculosis for Rapid, Real-Time, Non-Invasive Assessment of Drug and Vaccine Efficacy,” PLoS One, Vol. 7, No. 1, 2012, Article ID: e29774. http://dx.doi.org/10.1371/journal.pone.0029774
[15] National Committee for Clinical Laboratory Standards, “Susceptibility Testing of Mycobacteria, Nocardia, and Other Aerobic Actinomycetes; Approved Standard,” 2nd Edition, CLSI Document M24-A2, Vol. 31, No. 5, 2011, pp. 3-19.

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