Benzoxaboroles - Old compounds with new applications

Journal of Organometallic Chemistry

Volumn 694, Issue 22, 2009, Pages 3533-3541

  Adamczyk Woźniak, Agnieszka ^a   Cyrański, Michał K ^b   Zubrowska, Anna ^a   Sporzyński, Andrzej ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Applications; Benzoxaboroles; Boronic acids; Crystal structures; Properties; Synthesis

Indexed keywords

BENZOXABOROLES; BIOLOGICAL ACTIVITIES; BORONIC ACIDS; BUILDING BLOCKES; CLINICAL TRIAL; GLYCOCONJUGATES; HYDROXYL COMPOUNDS; METHODS OF SYNTHESIS; MOLECULAR RECEPTORS; NEW APPLICATIONS; ORGANIC SYNTHESIS; PHENYLBORONIC ACIDS; PROPERTIES; PROTECTING GROUP; SYNTHESIS; TITLE COMPOUNDS;

SUGAR (SUCROSE); SUGARS;

COMPLEXATION;

EID: 69949091362     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.07.022     Document Type: Review

References (65)

1. In: Hall D.G. (Ed). Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine (2005), Wiley-VCH, Weinheim, Germany
2. Maly K.E., Malek N., Fournier J.-H., Rodriguez-Cuamatzi P., Maris T., and Wuest J.D. Pure Appl. Chem. 78 (2006) 1305
3. Rodriguez-Cuamatzi P., Vargas-Diaz G., and Höpfl H. Angew. Chem., Int. Ed. 43 (2004) 3041
4. Rogowska P., Cyrański M.K., Sporzyński A., and Ciesielski A. Tetrahedron Lett. 47 (2006) 1389
5. Shimpi M.R., SeethaLekshmi N., and Pedireddi V.R. Cryst. Growth Des. 7 (2007) 1958
6. James T.D., Phillips M.D., and Shinkai S. Boronic Acids in Saccharide Recognition (2006), Boronic Acids in Saccharide Recognition, Cambridge, UK
7. Fujita N., Shinkai S., and James T.D. Chem. Asian J. 3 (2008) 1076
8. Torssell K. Ark. Kemi. 10 (1957) 507
9. Haynes R.R., and Snyder H.R. J. Org. Chem. 29 (1964) 3229
10. Baker S.J., Zhang Y.-K., Akama T., Lau A., Zhou H., Hernandez V., Mao W., Alley M.R.K., Sanders V., and Plattner J.J. J. Med. Chem. 49 (2006) 4447
11. 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., and Alley M.R.K. Science 316 (2007) 1759
12. Anacor Pharmaceuticals, CA, USA, .
13. Falck J.R., Bondlela M., Venkataraman S.K., and Srinivas D. J. Org. Chem. 66 (2001) 7148
14. Zhdankin V.V., Persichini III P.J., Zhang L., Fix S., and Kiprof P. Tetrahedron Lett. 40 (1999) 6705
15. Houben-Weyl, Methoden der Organischen Chemie, Organobor-Verbindungen III, vol. XII/3c, Georg Thieme Verlag, Stuttgart, Germany, 1984.
16. Cambridge Structural Database, see:. Allen F.H. Acta Cryst. B 58 (2002) 380
17. Cyrański M.K., Jezierska A., Klimentowska P., Panek J.J., and Sporzyński A. J. Phys. Org. Chem. 21 (2008) 472
18. Based on geometries of benzoxaboroles discussed in this article.
19. Da{ogonek}browski M., Kurach P., Luliński S., and Serwatowski J. Appl. Organometal. Chem. 21 (2007) 234
20. Luliński S., and Serwatowski J. J. Organomet. Chem. 692 (2007) 2924
21. Arcus V.L., Main L., and Nicholson B.K. J. Organomet. Chem. 460 (1993) 139
22. Tan Y.-L., White A.J.P., Widdowson D.A., Wilhelm R., and Williams D.J. J. Chem. Soc., Perkin Trans. 1 (2001) 3269
23. Sporzyński A., Lewandowski M., Rogowska P., and Cyrański M.K. Appl. Organometal. Chem. 19 (2005) 1202
24. Yamamoto Y., Ishii J., Nishiyama H., and Itoh K. J. Am. Chem. Soc. 127 (2005) 9625
25. Cummings W.M.C., Cox C.H., and Snyder H.R. J. Org. Chem. 34 (1969) 1669
26. Snyder H.R., Reedy A.J., and Lennarz W.J. J. Am. Chem. Soc. 20 (1958) 835
27. Luliński S., Madura I., Serwatowski J., Szatyłowicz H., and Zachara J. New J. Chem. 31 (2007) 144
28. Robin B., Buell G., Kiprof P., and Nemykin V.N. Acta Cryst. E 64 (2008) o314
29. Dowlut M., and Hall D.G. J. Am. Chem. Soc. 128 (2006) 4226
30. Bérubé M., Dowlut M., and Hall D.G. J. Org. Chem. 73 (2008) 6471
31. Grassberger M.A. Liebigs Ann. Chem. (1985) 683
32. Gunasekera D.S., Gerold D.J., Aalderks N.S., Chandra J.S., Maanu C.A., Kiprof P., Zhdankin V.V., and Reddy M.V.R. Tetrahedron 63 (2007) 9401
33. Hawkins R.T., Lennarz W.J., and Snyder H.R. J. Am. Chem. Soc. 82 (1960) 3053
34. Lennarz J., and Snyder R. J. Am. Chem. Soc. 82 (1960) 2172
35. Dale W.J., and Rush J.R. J. Org. Chem. 27 (1962) 2598
36. Miyaura N., and Suzuki A. J. Chem. Soc., Chem. Commun. (1979) 866
37. Tschampel P., and Snyder H.R. J. Org. Chem. 29 (1964) 2168
38. Murugesan N., Gu Z., Stein P.D., Bisaha S., Spergel S., Girotra R., Lee V.G., Lloyd J., Misra R.N., Schmidt J., Mathur A., Stratton L., Kelly Y.F., Bird E., Waldron T., Liu E.C.-K., Zhang R., Lee H., Serafino R., Abboa-Offei B., Mathers P., Giancarli M., Seymour A.A., Webb M.L., Moreland S., Barrish J.C., and Hunt J.T. J. Med. Chem. 41 (1998) 5198
39. Nicolaou K.C., Natarajan S., Li H., Jain N.F., Hughes R., Solomon M.E., Ramanjulu J.M., Boddy C.N.C., and Takayanagi M. Angew. Chem., Int. Ed. 37 (1998) 2708
40. Nicolaou K.C., Ramanjulu J.M., Natarajan S., Bräse S., Li H., Boddy C.N.C., and Rübsam F. Chem. Commun. (1997) 1899
41. Tessier P.E., Nguyen N., Clay M.D., and Fallis A.G. Org. Lett. 7 (2005) 767
42. Brown A.G., Crimmin M.J., and Edwards P.D. J. Chem. Soc., Perkin Trans. 1 (1992) 123
43. Link J.T., Sorensen B.K., Patel J., Emery M., Grynfarb M., and Goos-Nilsson A. Bioorg. Med. Chem. Lett. 14 (2004) 2209
44. Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., and Rübsam F. Chem. Eur. J. 5 (1999) 2584
45. Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., and Hughes R. Chem. Eur. J. 5 (1999) 2622
46. Yamamoto Y., Ishii J., Nishiyama H., and Itoh K. Tetrahedron 61 (2005) 11501
47. Prieto M., Mayor S., Rodriguez K., Lloyd-Williams P., and Giralt E. J. Org. Chem. 72 (2007) 1047
48. Gallant M., Belley M., Carrière M.-C., Chateauneuf A., Denis D., Lachance N., Lamontagne S., Metters K.M., Sawyer N., Slipetz D., Truchon J.F., and Labelle M. Bioorg. Med. Chem. Lett. 13 (2003) 3813
49. Nicolaou K.C., Li H., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., and Solomon M.E. Chem. Eur. J. 5 (1999) 2602
50. Oshima K., and Aoyama Y. J. Am. Chem. Soc. 121 (1999) 2315
51. Alexander C., Smith C.R., Whitcombe M.J., and Vulfson E.N. J. Am. Chem. Soc. 121 (1999) 6640
52. Ramström O., and Mosbach K. Curr. Opin. Chem. Biol. 3 (1999) 759
53. Wulff G. Pure Appl. Chem. 54 (1982) 2093
54. Kim Y., Hildebrand S.A., Weissleder R., and Tung C.-H. Chem. Commun. (2007) 2299
55. Ricardo A., Frye F., Carrigan M.A., Tipton J.D., Powell D.H., and Benner S.A. J. Org. Chem. 71 (2006) 9503
56. A.P. Russell, C.W. Zepp, US Patent 5512246, 1996.
57. Hui X., Baker S.J., Wester R.C., Barbadillo S., Cashmore A.K., Sanders V., Hold K.M., Akama T., Zhang Y.-K., Plattner J.J., and Maibach H.I. J. Pharm. Sci. 96 (2007) 2622
58. Baker S.J., Hui X., and Maibach H.I. Ann. Rep. Med. Chem. 40 (2005) 323
59. Alley M.R., Baker S.J., Beutner K.R., and Plattner J. Expert Opin. Inv. Drugs 16 (2007) 157
60. Baker S.J., Zhang Y.-K., Akama T., Wheeler C., Plattner J.J., Rosser R.M., Reid R.P., and Nixon N.S. J. Labelled Compd. Rad. 50 (2007) 245
61. Anacor Pharmaceuticals, CA, USA, Expert Rev. Clin. Immunol. 4 (2008) 309.
62. V. Sanders, K.R. Maples, J.J. Plattner, C. Bellinger-Kawahara, PCT Int. Appl. WO2007146965, 2007.
63. C.R. Lowe, F.K. Sartain, X. Yang, PCT Int. Appl. WO2006079843, 2006.
64. P.W. Austin, C.J. Kneale, P.J. Crowley, J.M. Clough, PCT Int. Appl. WO9533754, 1995.
65. M. Singer, US Patent, 3873279, 1975.