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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access November 29, 2012

Susceptibility to hydrolysis of phenylboronic pinacol esters at physiological pH

Cesare Achilli EMAIL logo , Annarita Ciana , Maurizio Fagnoni , Cesare Balduini and Giampaolo Minetti
From the journal Open Chemistry


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.

[1] W. Yang, X. Gao, B. Wang, Med. Res. Rev. 23, 346 (2003) in Google Scholar PubMed

[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) in Google Scholar PubMed

[3] A.K. Asbury, R.G. Ojemann, S.L. Nielsen, W.H. Sweet, J. Neuropathol. Exp. Neurol. 31, 278 (1972) in Google Scholar PubMed

[4] K. Taniyama, H. Fujiwara, T. Kuno, N. Saito, H. Shuntoh, M. Sakaue, C. Tanaka, Pigment Cell Res. 2, 291 (1989) in Google Scholar PubMed

[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) in Google Scholar

[6] I. Dasgupta, E.A. Tanifum, M. Srivastava, S.S. Phatak, C.N. Cavasotto, M. Analoui, A. Annapragada, PLoS One 7, e29585 (2012) in Google Scholar PubMed PubMed Central

[7] R. Bernardini, A. Oliva, A. Paganelli, E. Menta, M. Grugni, S. De Munari, L. Goldoni, Chem. Lett. 38, 750 (2009) in Google Scholar

[8] H.G. Kuivila, A.H. Keough, E.J. Soboczenski, J. Org. Chem. 8, 780 (1954) in Google Scholar

[9] R.A. Bowie, O.C. Musgrave, J. Chem. Soc. 3945 (1963) 10.1039/jr9630003945Search in Google Scholar

[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) in Google Scholar PubMed

[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) in Google Scholar

[12] R.D. Pizer, A.A. Tihal, Polyhedron 15, 3411 (1996) in Google Scholar

[13] C. Hansch, A. Leo, Substituent constants for correlation analysis in chemistry and biology (J. Wiley and Sons, New York, 1979) Search in Google Scholar

[14] J. Yan, G. Springsteen, S. Deeter, B. Wang, Tetrahedron 60, 11205 (2004) in Google Scholar

Published Online: 2012-11-29
Published in Print: 2013-2-1

© 2013 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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