PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2013 | 11 | 2 | 137-139
Article title

Susceptibility to hydrolysis of phenylboronic pinacol esters at physiological pH

Content
Title variants
Languages of publication
EN
Abstracts
EN
Boronic acids and their esters are highly considered compounds for the design of new drugs and drug delivery devices, particularly as boron-carriers suitable for neutron capture therapy. However, these compounds are only marginally stable in water. Hydrolysis of some phenylboronic pinacol esters is described here. The kinetics is dependent on the substituents in the aromatic ring. Also the pH strongly influences the rate of the reaction, which is considerably accelerated at physiological pH. Therefore, care must be taken when considering these boronic pinacol esters for pharmacological purposes. [...]
Publisher

Journal
Year
Volume
11
Issue
2
Pages
137-139
Physical description
Dates
published
1 - 2 - 2013
online
29 - 11 - 2012
Contributors
  • Laboratories of Biochemistry, Department of Biology and Biotechnology “Lazzaro Spallanzani”, University of Pavia, 21-27100, Pavia, Italy
  • Laboratories of Biochemistry, Department of Biology and Biotechnology “Lazzaro Spallanzani”, University of Pavia, 21-27100, Pavia, Italy
  • Department of Chemistry, University of Pavia, 12-27100, Pavia, Italy
  • Laboratories of Biochemistry, Department of Biology and Biotechnology “Lazzaro Spallanzani”, University of Pavia, 21-27100, Pavia, Italy
  • Laboratories of Biochemistry, Department of Biology and Biotechnology “Lazzaro Spallanzani”, University of Pavia, 21-27100, Pavia, Italy, minetti@unipv.it
References
  • [1] W. Yang, X. Gao, B. Wang, Med. Res. Rev. 23, 346 (2003) http://dx.doi.org/10.1002/med.10043[Crossref]
  • [2] A.H. Soloway, W. Tjarks, B.A. Barnum, F.G. Rong, R.F. Barth, I.M. Codogni, J.G. Wilson, Chem. Rev. 98, 1515 (1998) http://dx.doi.org/10.1021/cr941195u[Crossref]
  • [3] A.K. Asbury, R.G. Ojemann, S.L. Nielsen, W.H. Sweet, J. Neuropathol. Exp. Neurol. 31, 278 (1972) http://dx.doi.org/10.1097/00005072-197204000-00005[Crossref]
  • [4] K. Taniyama, H. Fujiwara, T. Kuno, N. Saito, H. Shuntoh, M. Sakaue, C. Tanaka, Pigment Cell Res. 2, 291 (1989) http://dx.doi.org/10.1111/j.1600-0749.1989.tb00207.x[Crossref]
  • [5] D.G. Hall, Structure, Properties, and Preparation of Boronic Acid Derivatives, in Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd edition (Wiley-VCH Verlag GmbH & Co., Weinheim, 2011) http://dx.doi.org/10.1002/9783527639328[Crossref]
  • [6] I. Dasgupta, E.A. Tanifum, M. Srivastava, S.S. Phatak, C.N. Cavasotto, M. Analoui, A. Annapragada, PLoS One 7, e29585 (2012) http://dx.doi.org/10.1371/journal.pone.0029585[Crossref]
  • [7] R. Bernardini, A. Oliva, A. Paganelli, E. Menta, M. Grugni, S. De Munari, L. Goldoni, Chem. Lett. 38, 750 (2009) http://dx.doi.org/10.1246/cl.2009.750[Crossref]
  • [8] H.G. Kuivila, A.H. Keough, E.J. Soboczenski, J. Org. Chem. 8, 780 (1954) http://dx.doi.org/10.1021/jo01370a013[Crossref]
  • [9] R.A. Bowie, O.C. Musgrave, J. Chem. Soc. 3945 (1963) [Crossref]
  • [10] T.I. Lazarova, L. Jin, M. Rynkiewicz, J.C. Gorga, F. Bibbins, H.V. Meyers, R. Babine, J. Strickler, Bioorg. Med. Chem. Lett. 16, 5022 (2006) http://dx.doi.org/10.1016/j.bmcl.2006.07.043[Crossref]
  • [11] S.R. Inglis, A. Zervosen, E.C. Woon, T. Gerards, N. Teller, D.S. Fischer, A. Luxen, C.J. Schofield, J. Med. Chem. 52, 6097 (2009) http://dx.doi.org/10.1021/jm9009718[Crossref]
  • [12] R.D. Pizer, A.A. Tihal, Polyhedron 15, 3411 (1996) http://dx.doi.org/10.1016/0277-5387(96)00042-3[Crossref]
  • [13] C. Hansch, A. Leo, Substituent constants for correlation analysis in chemistry and biology (J. Wiley and Sons, New York, 1979)
  • [14] J. Yan, G. Springsteen, S. Deeter, B. Wang, Tetrahedron 60, 11205 (2004) http://dx.doi.org/10.1016/j.tet.2004.08.051[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0159-2
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.