Synthesis and biological evaluation of novel benzoxaboroles as potential antimicrobial and anticancer agents

Journal of Heterocyclic Chemistry

Volumn 50, Issue 4, 2013, Pages 814-820

  Sravan Kumar, J ^a   Alam, M A ^a   Gurrapu, Shirisha ^a   Nelson, Grady ^a   Williams, Michael ^a   Corsello, Michael A ^b   Johnson, Joseph L ^a   Jonnalagadda, Subash C ^b   Mereddy, Venkatram R ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b ROWAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 FORMYLPHENYLBORONIC ACID; ANTINEOPLASTIC AGENT; BENZOXABOROLE DERIVATIVE; BORONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ALLYLATION; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BARBIER ALLYLATION; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PASSERINI REACTION;

EID: 84880931354     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.1777     Document Type: Article

References (44)

1. (a), Burroughs, S.,;, Wang, B., Chem Bio Chem 2010, 11, 2245
2. (b), Trippier, P. C.,;, McGuigan, C., Med Chem Comm 2010, 1, 183
3. (c), Yang, W.,;, Gao, X.,;, Wang, B., Med Res Rev 2003, 23, 346
4. (d), Dembitsky, V. M.,;, Srebnik, M., Tetrahedron 2003, 59, 579
5. (e), Coutts, S. J.,;, Kelly, T. A.,;, Snow, R. J.,;, Kennedy, C. A.,;, Barton, R. W.,;, Adams, J.,;, Krolikowski, D. A.,;, Freeman, D. M.,;, Campbell, S. J.,;, Ksiazek, J. F.,;, Bachovchin, W. W. J, Med Chem 1996, 39, 2087
6. (f), Kinder, D. H.,;, Frank, S. K.,;, Ames, M. M. J, Med Chem 1990, 33, 819
7. (g), Kettner, C. A.,;, Shenvi, A. B. J, Biol Chem 1984, 259, 15106.
8. (a), Nicolaou, K. C.,;, Natarajan, S.,;, Li, H.,;, Jain, N. F.,;, Hughes, R.,;, Solomon, M. E.,;, Ramanjulu, J. M.,;, Boody, C. N. C.,;, Takayanagi, M., Angew Chem Int Ed 1998, 37, 2708
9. (b), Nicolaou, K. C.,;, Li, H.,;, Boody, C. N. C.,;, Ramanjulu, J. M.,;, Yue, T. Y.,;, Natarajan, S.,;, Chu, X. J.,;, Brase, S.,;, Rubsam, F., Chem Eur 1999, 5, 2584
10. (c), Tan, Y. L.,;, White, A. J. P.,;, Widdowson, D. A.,;, Wilhelm, R.,;, Williams, D. J. J, Chem Soc Perkin Trans 2001, 1, 3269
11. (d), Wozniack, A. A.,;, Cyranski, M. K.,;, Zubrowska, A.,;, Sporzynski, A. J, Organomet Chem 2009, 694, 3533 and references therein
12. (e), Ye, L.,;, Ding, D.,;, Feng, Y.,;, Xie, D.,;, Wu, P.,;, Guo, H.,;, Meng, Q.,;, Zhou, H., Tetrahedron 2009, 65, 8738
13. (f), Ma, X.,;, Yang, Z.,;, Wang, X.,;, Roesky, H. W.,;, Wu, F.,;, Zhu, H., Inorg Chem 2011, 50, 2010.
14. (a), Oshima, K.,;, Aoyama, Y. J, Am Chem Soc 1999, 121, 2315
15. (b), Dowlut, M.,;, Hall, D. G. J, Am Chem Soc 2006, 128, 4226
16. (c), Pal, A.,;, Berube, M.,;, Hall, D. G., Angew Chem Int Ed Engl 2010, 49, 1492
17. (d), Schumacher, S.,;, Katterle, M.,;, Hettrich, C.,;, Paulke, B-R.,;, Hall, D. G.,;, Scheller, F. W.,;, Gajovic-Eichelmann, N. J., Mol. Recognition 2011, 24, 953
18. (e), Schumacher, S.,;, Grueneberger, F.,;, Katterle, M.,;, Hettrich, C.,;, Hall, D. G.,;, Scheller, F. W.,;, Gajovic-Eichelmann, N., Polymer 2011, 52, 2485.
19. (a) AN2690, AN2718, & AN2728 are being currently developed as therapeutic agents by Anacor Pharmaceuticals Inc. Palo Alto: CA, USA
20. (b), Li, X.,;, Plattner, J. J.,;, Hernandez, V.,;, Ding, C. Z.,;, Wu, W.,;, Yang, Y.,;, Xu, M., Tetrahedron Lett 2011, 52, 4924
21. (c), Xia, Y.,;, Cao, K.,;, Zhou, Y.,;, Alley, M. R. K.,;, Rock, F.,;, Mohan, M.,;, Meewan, M.,;, Baker, S. J.,;, Lux, S.,;, Ding, C. Z.,;, Jia, G.,;, Kully, M.,;, Plattner, J. J., Bioorg Med Chem Lett 2011, 21, 2533
22. (d), Li, X.,;, Zhang, S.,;, Zhang, Y-K.,;, Liu, Y.,;, Ding, C. Z.,;, Zhou, Y.,;, Plattner, J. J.,;, Baker, S. J.,;, Bu, W.,;, Liu, L.,;, Kazmierski, W. M.,;, Duan, M.,;, Grimes, R. M.,;, Wright, L. L.,;, Smith, G. K.,;, Jarvest, R. L.,;, Ji, J-J.,;, Cooper, J. P.,;, Tallant, M. D.,;, Crosby, R. M.,;, Creech, K.,;, Ni, Z-J.,;, Zou, W.,;, Wright, J., Bioorg Med Chem Lett 2011, 21, 2048
23. (e), Zhang, Y-K.,;, Plattner, J. J.,;, Freund, Y. R.,;, Easom, E. E.,;, Zhou, Y.,;, Gut, J.,;, Rosenthal, P. J.,;, Waterson, D.,;, Gamo, F-J.,;, Angulo-Barturen, I.,;, Ge, M.,;, Li, Z.,;, Li, L.,;, Jian, Y.,;, Cui, H.,;, Wang, H.,;, Yang, J., Bioorg Med Chem Lett 2011, 21, 644
24. (f), Jacobs, R. T.,;, Plattner, J. J.,;, Nare, B.,;, Wring, S. A.,;, Chen, D.,;, Freund, Y.,;, Gaukel, E. G.,;, Orr, M. D.,;, Perales, J. B.,;, Jenks, M.,;, Noe, R. A.,;, Sligar, J. M.,;, Zhang, Y.-K.,;, Bacchi, C. J.,;, Yarlett, N.,;, Don, R., Future Med. Chem. 2011, 3, 1259
25. (g), Ding, D.,;, Meng, Q.,;, Gao, G.,;, Zhao, Y.,;, Wang, Q.,;, Nare, B.,;, Jacobs, R.,;, Rock, F.,;, Alley, M. R. K.,;, Plattner, J. J.,;, Chen, G.,;, Li, D.,;, Zhou, H. J., Med Chem 2011, 54, 1276
26. (h), Li, X.,;, Zhang, Y-K.,;, Liu, Y.,;, Zhang, S.,;, Ding, C. Z.,;, Zhou, Y.,;, Plattner, J. J.,;, Baker, S. J.,;, Liu, L.,;, Bu, W.,;, Kazmierski, W. M.,;, Wright, L. L.,;, Smith, G. K.,;, Jarvest, R. L.,;, Duan, M.,;, Ji, J-J.,;, Cooper, J. P.,;, Tallant, M. D.,;, Crosby, R. M.,;, Creech, K.,;, Ni, Z-J.,;, Zou, W.,;, Wright, J., Bioorg Med Chem Lett 2010, 20, 7493
27. (i), Ding, C. Z.,;, Zhang, Y-K.,;, Li, X.,;, Liu, Y.,;, Zhang, S.,;, Zhou, Y.,;, Plattner, J. J.,;, Baker, S. J.,;, Liu, L.,;, Duan, M.,;, Jarvest, R. L.,;, Ji, J.,;, Kazmierski, W. M.,;, Tallant, M. D.,;, Wright, L. L.,;, Smith, G. K.,;, Crosby, R. M.,;, Wang, A. A.,;, Ni, Z-J.,;, Zou, W.,;, Wright, J., Bioorg Med Chem Lett 2010, 20, 7317
28. (j), Ding, D.,;, Zhao, Y.,;, Meng, Q.,;, Xie, D.,;, Nare, B.,;, Chen, D.,;, Bacchi, C. J.,;, Yarlett, N.,;, Zhang, Y-K.,;, Hernandez, V.,;, Xia, Y.,;, Freund, Y.,;, Abdulla, M.,;, Ang, K-H.,;, Ratnam, J.,;, McKerrow, J. H.,;, Jacobs, R. T.,;, Zhou, H.,;, Plattner, J., J. Med. Chem. Lett. 2010, 1, 165
29. (k), Zhang, Y-K.,;, Plattner, J. J.,;, Akama, T.,;, Baker, S. J.,;, Hernandez, V. S.,;, Sanders, V.,;, Freund, Y.,;, Kimura, R.,;, Bu, W.,;, Hold, K. M.,;, Lu, X-S., Bioorg Med Chem Lett 2010, 20, 2270
30. (l), Akama, T.,;, Baker, S. J.,;, Zhang, Y. K.,;, Hernandez, V.,;, Zhou, H.,;, Sanders, V.,;, Freund, Y.,;, Kimura, R.,;, Maples, K. R.,;, Plattner, J. J., Bioorg Med Chem Lett 2009, 19, 2129
31. (m), Baker, S. J.,;, Zhang, Y. K.,;, Akama, T.,;, Lau, A.,;, Zhou, H.,;, Hernandez, V.,;, Mao W.,;, Alley, M. R. K.,;, Sanders, V.,;, Plattner, J. J. J., Med Chem 2006, 49, 4447.
32. Mahalingam, A.,;, Geonnotti, A. R.,;, Balzarini, J.,;, Kiser, P. F., Mol Pharm, 2011, 8, 2465
33. (b), Jay, J. I.,;, Lai, B. E.,;, Myszka, D. G.,;, Mahalingam, A.,;, Langheinrich, K.,;, Katz, D. F.,;, Kiser, P. F., Mol Pharm 2010, 7, 116.
34. (a), Jonnalagadda, S. C.,;, Cruz, J.,;, Connell, R. J.,;, Scott, P.,;, Mereddy, V. R., Tetrahedron Lett 2009, 50, 4314
35. (b), Banfi, L.,;, Riva, R., Org React 2005, 65, 1
36. (c), Domling, A.,;, Ugi, I., Angew Chem Int Ed 2000, 39, 3168.
37. (a), Basavaiah D.,;, Reddy B. S.,;, Badsara S. S., Chem Rev, 2010, 110, 5447
38. (b), Declerck V.,;, Martinez J.,;, Lamaty F., Chem Rev 2009, 109, 1.
39. (c), Singh V.,;, Batra S., Tetrahedron 2008, 64, 4511
40. (d), Basavaiah D.,;, Rao K. V.,;, Reddy R. J., Chem Soc Rev 2007, 36, 1581
41. (e), Basavaiah D.,;, Rao A. J.,;, Satyanarayana T., Chem Rev 2003, 103, 811.
42. (a), Kumar, J. S.,;, Bashian, C. M.,;, Corsello, M. A.,;, Jonnalagadda, S. C.,;, Mereddy, V. R., Tetrahedron Lett 2010, 51, 4482
43. (b), Kumar, J. S.,;, Jonnalagadda, S. C.,;, Mereddy, V. R., Tetrahedron Lett 2010, 51, 779
44. (c), Gunasekera, D. S.,;, Gerold, D. A.,;, Aalderks, N. A.,;, Jonnalagadda, S. C.,;, Kiprof, P.,;, Zhdankin, V. V.,;, Reddy, M. V. R., Tetrahedron 2007, 63, 9401.