Synthesis and Biological Activity of Novel 6-Substituted Purine Derivatives
DOI:
https://doi.org/10.29356/jmcs.v54i2.948Keywords:
6-Substituted purines, 2-amino-6-chloropurine, Synthesis, Antifungal ActivityAbstract
A series of 6-substituted purines were synthesized from commercially available 2-amino-6-chloropurine with appropriate reagents, and nine new compounds 7, 8, and 11-17 have been discovered. The compounds synthesized were identified by elemental analysis, 1H NMR, as well as mass spectral data. All the title compounds were screened for their antifungal activities, under the method of the disc diffusion, using three species of fungi — Bacillus subtillis, Aspergillus niger, and Candida tropicalis— and some of the compounds showed promising activities.
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References
1. Draanen, N. A. V. G.; Freeman, A.; Short, S. A.; Harvey, R.; Jansen, R.; Szczech, G.; Koszalka, G. W. J. Med. Chem. 1996, 39, 538-542.
2. Pang, R. F.; Zhang, C. L.; Yuan, D. K.; Yang, M. Bioorg. Med. Chem. 2008, 16, 8178-8186.
3. Whitley, R. J.; Alford, C. A. Ann. Rev. Microbiol. 1978, 32, 285300.
4. Hahn, H.; Bopp, M. Biol. Unserer Zeit 1981, 11, 113-120.
5. Havlieek, L.; Hanu, J.; Vesely, J.; Leclercq, S.; Meier, L.; Shaw, G.; Strnad, M. J. Med. Chem. 1997, 40, 408-412.
6. Jacobson, K. A.; Van Galen, P. J. M.; Williams, M. J. Med. Chem. 1992, 35, 407-422.
7. Griffin, R. J.; Arris, C. E.; Bleasdale, C.; Boyle, F. T.; Calvert, A. H.; Curtin, N. J.; Dalby, C.; Kanugula, S.; Lembicz, N. K.; Newell, D. R.; Pegg, A. E.; Golding, B. T. J. Med. Chem. 2000, 43, 4071-4083.
8. Dolan, M. E.; Pegg, A. E. Clin. Cancer. Res. 1997, 3, 837-847.
9. Meerbach, A.; Neyts, J.; Holy, A.; Wutzler, P.; Clercq, E. D. Antivir. Chem. Chemother. 1998, 9, 275-282.
10. Fleysher, M. H.; Bernacki, R. J.; Bullard, G. A. J. Med. Chem. 1980, 23, 1448-1452.
11. Vaidyanathan, G.; Affleck, D. J.; Cavazos, C. M.; Johnson, S. P.; Shankar, S.; Friedman, H. S.; Colvin, M. O.; Zalutsky, M. R. Bioconjugate Chem. 2000, 11, 868-875.
12. Belanich, M.; Pastor, M.; Randall, T.; Guerra, D.; Kibitel, J.; Alas, L.; Li, B.; Citron, M.; Wasserman, P.; White, A.; Eyre, H.; Jaeckle, K.; Shulman, S.; Rector, D.; Prados, M.; Coons, S.; Shapiro, W.; Yarosh, D. B. Cancer Res. 1996, 56, 783-788.
13. Harmse, L.; Zyla, R. V.; Grayb, N.; Schultzb, S. P.; Leclercc, L.; Meijerc, C. D.; Havlika, I. Biochem. Pharmacol. 2001, 62, 341348.
14. Gibson, A. E.; Arris, C. E.; Bentley, J.; Boyle, F. T.; Curtin, N. J.; Davies, T. G.; Endicott, J. A.; Golding, B. T.; Grant, S.; Griffin, R. J.; Jewsbury, P.; Johnson, L. N.; Mesguiche, V.; Newell, D. R.; Noble, M. E. M.; Tucker, J. A.; Whitfield, H. J. J. Med. Chem. 2002, 45, 3381-3393.
15. Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Org. Chem. 1976, 41, 158-159.
16. Xu, K. X. Processing of fine chemical industrial raw materials and intermediates, Chemical Industry Press, Beijing, 1998, pp 114-117.
17. Tuttle, J. V.; Tisdale, M.; Krenitsky, T. A. J. Med. Chem. 1993, 36, 119-125.
18. Huang, L. K.; Cherng, Y. C.; Cheng, Y. R.; Jang, J. P.; Chao, Y. L.; Cherng, Y. J. Tetrahedron 2007, 63, 5323-5327.
19. Bauman, J. G.; Wirsching, R. C. US patent 5602246 1997.
20. Chang, Y.; Cai, C. Tetrahedron Lett. 2005, 46, 3161-3164.
21. Sylvia, M. T.; Joel, V. T.; Martin, J. S.; Susan, M. D.; Wayne, H. M.; Thomas, A. K. George, W. K. US patent 5420115 1995.
22. Mcelhinney, R. S.; Donnelly, D. J.; Mccormick, J. E.; Kelly, J.; Watson, A. J.; Rafferty, J. A.; Elder, R. H.; Middleton, M. R.; Willington, M. A.; Mcmurry, T. B. H.; Margison, G. P. J. Med. Chem. 1998, 41, 5265-5271.
23. Moosdeen, F.; Williams, J. D.; Secker, A. J. Antimicrob. Chemother. 1988, 21, 439-443.
24. Kimura, Y.; Yu, L. J.; Hirano, Y.; Suzuki, H.; Wang, Z. Y. J. Biol. Chem. 2009, 284, 93-99.
2. Pang, R. F.; Zhang, C. L.; Yuan, D. K.; Yang, M. Bioorg. Med. Chem. 2008, 16, 8178-8186.
3. Whitley, R. J.; Alford, C. A. Ann. Rev. Microbiol. 1978, 32, 285300.
4. Hahn, H.; Bopp, M. Biol. Unserer Zeit 1981, 11, 113-120.
5. Havlieek, L.; Hanu, J.; Vesely, J.; Leclercq, S.; Meier, L.; Shaw, G.; Strnad, M. J. Med. Chem. 1997, 40, 408-412.
6. Jacobson, K. A.; Van Galen, P. J. M.; Williams, M. J. Med. Chem. 1992, 35, 407-422.
7. Griffin, R. J.; Arris, C. E.; Bleasdale, C.; Boyle, F. T.; Calvert, A. H.; Curtin, N. J.; Dalby, C.; Kanugula, S.; Lembicz, N. K.; Newell, D. R.; Pegg, A. E.; Golding, B. T. J. Med. Chem. 2000, 43, 4071-4083.
8. Dolan, M. E.; Pegg, A. E. Clin. Cancer. Res. 1997, 3, 837-847.
9. Meerbach, A.; Neyts, J.; Holy, A.; Wutzler, P.; Clercq, E. D. Antivir. Chem. Chemother. 1998, 9, 275-282.
10. Fleysher, M. H.; Bernacki, R. J.; Bullard, G. A. J. Med. Chem. 1980, 23, 1448-1452.
11. Vaidyanathan, G.; Affleck, D. J.; Cavazos, C. M.; Johnson, S. P.; Shankar, S.; Friedman, H. S.; Colvin, M. O.; Zalutsky, M. R. Bioconjugate Chem. 2000, 11, 868-875.
12. Belanich, M.; Pastor, M.; Randall, T.; Guerra, D.; Kibitel, J.; Alas, L.; Li, B.; Citron, M.; Wasserman, P.; White, A.; Eyre, H.; Jaeckle, K.; Shulman, S.; Rector, D.; Prados, M.; Coons, S.; Shapiro, W.; Yarosh, D. B. Cancer Res. 1996, 56, 783-788.
13. Harmse, L.; Zyla, R. V.; Grayb, N.; Schultzb, S. P.; Leclercc, L.; Meijerc, C. D.; Havlika, I. Biochem. Pharmacol. 2001, 62, 341348.
14. Gibson, A. E.; Arris, C. E.; Bentley, J.; Boyle, F. T.; Curtin, N. J.; Davies, T. G.; Endicott, J. A.; Golding, B. T.; Grant, S.; Griffin, R. J.; Jewsbury, P.; Johnson, L. N.; Mesguiche, V.; Newell, D. R.; Noble, M. E. M.; Tucker, J. A.; Whitfield, H. J. J. Med. Chem. 2002, 45, 3381-3393.
15. Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Org. Chem. 1976, 41, 158-159.
16. Xu, K. X. Processing of fine chemical industrial raw materials and intermediates, Chemical Industry Press, Beijing, 1998, pp 114-117.
17. Tuttle, J. V.; Tisdale, M.; Krenitsky, T. A. J. Med. Chem. 1993, 36, 119-125.
18. Huang, L. K.; Cherng, Y. C.; Cheng, Y. R.; Jang, J. P.; Chao, Y. L.; Cherng, Y. J. Tetrahedron 2007, 63, 5323-5327.
19. Bauman, J. G.; Wirsching, R. C. US patent 5602246 1997.
20. Chang, Y.; Cai, C. Tetrahedron Lett. 2005, 46, 3161-3164.
21. Sylvia, M. T.; Joel, V. T.; Martin, J. S.; Susan, M. D.; Wayne, H. M.; Thomas, A. K. George, W. K. US patent 5420115 1995.
22. Mcelhinney, R. S.; Donnelly, D. J.; Mccormick, J. E.; Kelly, J.; Watson, A. J.; Rafferty, J. A.; Elder, R. H.; Middleton, M. R.; Willington, M. A.; Mcmurry, T. B. H.; Margison, G. P. J. Med. Chem. 1998, 41, 5265-5271.
23. Moosdeen, F.; Williams, J. D.; Secker, A. J. Antimicrob. Chemother. 1988, 21, 439-443.
24. Kimura, Y.; Yu, L. J.; Hirano, Y.; Suzuki, H.; Wang, Z. Y. J. Biol. Chem. 2009, 284, 93-99.
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2019-06-17
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