Examination of the reactivity of benzoxaboroles and related compounds with a cis -diol

Journal of Organic Chemistry

Volumn 77, Issue 24, 2012, Pages 11200-11209

  Tomsho, John W ^a,b   Benkovic, Stephen J ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF THE SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIZARIN RED; BENZOXABOROLE; BORONATE; DRUG DISCOVERY; FLUORESCENT DYES; PHENYLBORONIC ACIDS; PHYSIOLOGICAL CONDITION; RELATED COMPOUNDS; STRUCTURAL ORIGIN;

DYES; SCAFFOLDS;

ORGANIC ACIDS;

ALIZARIN RED S; BENZENEBORONIC ACID; BENZOXABOROLE; BORONIC ACID DERIVATIVE; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ISOTHERMAL TITRATION CALORIMETRY; STEADY STATE; ULTRAVIOLET SPECTROSCOPY;

EID: 84871542619     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302264g     Document Type: Article

References (22)

1. Torssell, K. Ark. Kemi 1957, 10, 507-511
2. Li, X.; Zhang, Y.-K.; Liu, Y.; Ding, C. Z.; Li, Q.; Zhou, Y.; Plattner, J. J.; Baker, S. J.; Qian, X.; Fan, D.; Liao, L.; Ni, Z.-J.; White, G. V.; Mordaunt, J. E.; Lazarides, L. X.; Slater, M. J.; Jarvest, R. L.; Thommes, P.; Ellis, M.; Edge, C. M.; Hubbard, J. A.; Somers, D.; Rowland, P.; Nassau, P.; McDowell, B.; Skarzynski, T. J.; Kazmierski, W. M.; Grimes, R. M.; Wright, L. L.; Smith, G. K.; Zou, W.; Wright, J.; Pennicott, L. E. Bioorg. Med. Chem. Lett. 2010, 20, 3550-3556
3. Dixon, D. D.; Lockner, J. W.; Zhou, Q.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 8432-8435
4. Snyder, H. R.; Reedy, A. J.; Lennarz, W. J. J. Am. Chem. Soc. 1958, 80, 835-838
5. Dowlut, M.; Hall, D. G. J. Am. Chem. Soc. 2006, 128, 4226-4227
6. Bérubé, M.; Dowlut, M.; Hall, D. G. J. Org. Chem. 2008, 73, 6471-6479
7. Tomsho, J. W.; Pal, A.; Hall, D. G.; Benkovic, S. J. ACS Med. Chem. Lett. 2012, 3, 48-52
8. Adamczyk-Woźniak, A.; Cyrański, M. K.; Ż ubrowska, A.; Sporzyński, A. J. Organomet. Chem. 2009, 694, 3533-3541
9. Baker, S. J.; Tomsho, J. W.; Benkovic, S. J. Chem. Soc. Rev. 2011, 40, 4279-4285
10. Rock, F. L.; Mao, W.; Yaremchuk, A.; Tukalo, M.; Crepin, T.; Zhou, H.; Zhang, Y. K.; Hernandez, V.; Akama, T.; Baker, S. J.; Plattner, J. J.; Shapiro, L.; Martinis, S. A.; Benkovic, S. J.; Cusack, S.; Alley, M. R. K. Science 2007, 316, 1759-1761
11. Obrecht, D.; Bernardini, G.; Dale, G.; Dembowsky, K. In Annual Reports in Medicinal Chemistry; Elsevier Inc.: New York, 2011; Vol. 46, pp 245-262.
12. 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, 1276-1287
13. Qiao, Z.; Wang, Q.; Zhang, F.; Wang, Z.; Bowling, T.; Nare, B.; Jacobs, R. T.; Zhang, J.; Ding, D.; Liu, Y.; Zhou, H. J. Med. Chem. 2012, 55, 3553-3557
14. 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, 2129-2132
15. 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, 2533-2536
16. Kim, H.; Kang, Y. J.; Kang, S.; Kim, K. T. J. Am. Chem. Soc. 2012, 134, 4030-4033
17. Ellis, G. A.; Palte, M. J.; Raines, R. T. J. Am. Chem. Soc. 2012, 134, 3631-3634
18. Tomsho, J. W.; Benkovic, S. J. J. Org. Chem. 2012, 77, 2098-2106
19. Huebner, A.; Qu, Z. W.; Englert, U.; Bolte, M.; Lerner, H. W.; Holthausen, M. C.; Wagner, M. J. J. Am. Chem. Soc. 2011, 133, 4596-4609
20. DiCesare, N.; Lakowicz, J. R. J. Phys. Chem. A 2001, 105, 6834-6840
21. Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 5874-5875
22. Springsteen, G. Tetrahedron 2002, 58, 5291-5300