Boron-containing inhibitors of synthetases

被引:204
作者
Baker, Stephen J. [1 ]
Tomsho, John W. [2 ]
Benkovic, Stephen J. [2 ]
机构
[1] Anacor Pharmaceut Inc, Palo Alto, CA 94303 USA
[2] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
CROSS-COUPLING REACTION; TRANSFER-RNA SYNTHETASE; B-11; NMR; COMPLEX-FORMATION; ANTIFUNGAL AGENT; KINETIC EVIDENCE; DRUG DISCOVERY; BORIC-ACID; MECHANISM; BORATE;
D O I
10.1039/c0cs00131g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The use of boron in small-molecule pharmaceuticals is increasing. Boron's ubiquitous occurrence in nature and the recent success of a boronic acid drug (Velcade (R)) in the clinic have alleviated many concerns over its use in pharmaceuticals. In addition, the unique physicochemical properties of boronic acids make them an attractive addition to the medicinal chemists toolbox. This tutorial review will discuss these properties and potential benefits for anyone interested in finding novel enzyme inhibitors. An exceptional class of boronic acids, the oxaboroles, will be highlighted and their properties and uses will be discussed in detail. Finally, the current paradigm for the reaction of boronic acids with enzyme nucleophiles will be summarized.
引用
收藏
页码:4279 / 4285
页数:7
相关论文
共 55 条
[1]   Benzoxaboroles - Old compounds with new applications [J].
Adamczyk-Wozniak, Agnieszka ;
Cyranski, Michal K. ;
Zubrowska, Anna ;
Sporzynski, Andrzej .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (22) :3533-3541
[2]   Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids [J].
Adams, J ;
Behnke, M ;
Chen, SW ;
Cruickshank, AA ;
Dick, LR ;
Grenier, L ;
Klunder, JM ;
Ma, YT ;
Plamondon, L ;
Stein, RL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (04) :333-338
[3]   Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis [J].
Akama, Tsutomu ;
Baker, Stephen J. ;
Zhang, Yong-Kang ;
Hernandez, Vincent ;
Zhou, Huchen ;
Sanders, Virginia ;
Freund, Yvonne ;
Kimura, Richard ;
Maples, Kirk R. ;
Plattner, Jacob J. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (08) :2129-2132
[4]   Discovery and Optimization of Boronic Acid Based Inhibitors of Autotaxin [J].
Albers, Harald M. H. G. ;
van Meeteren, Laurens A. ;
Egan, David A. ;
van Tilburg, Erica W. ;
Moolenaar, Wouter H. ;
Ovaa, Huib .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (13) :4958-4967
[5]  
ALI HA, 2005, CONT ASPECTS BORON C, P22
[6]   Anti-infectives - Recent progress on the topical therapy of onychomycosis [J].
Alley, Michael R. K. ;
Baker, Stephen J. ;
Beutner, Karl R. ;
Plattner, Jacob .
EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2007, 16 (02) :157-167
[7]   Design, synthesis, and biological evaluation of aminoboronic acids as growth-factor receptor inhibitors of EGFR and VEGFR-1 tyrosine kinases [J].
Asano, T ;
Nakamura, H ;
Uehara, Y ;
Yamamoto, Y .
CHEMBIOCHEM, 2004, 5 (04) :483-490
[8]   DYNAMICS OF BORON ACID COMPLEXATION REACTIONS - FORMATION OF 1-1 BORON ACID LIGAND COMPLEXES [J].
BABCOCK, L ;
PIZER, R .
INORGANIC CHEMISTRY, 1980, 19 (01) :56-61
[9]   Inhibition of Mn-2(2+)-arginase by borate leads to the design of a transition state analogue inhibitor, 2(S)-amino-6-boronohexanoic acid [J].
Baggio, R ;
Elbaum, D ;
Kanyo, ZF ;
Carroll, PJ ;
Cavalli, RC ;
Ash, DE ;
Christianson, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8107-8108
[10]   Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of onychomycosis [J].
Baker, Stephen J. ;
Zhang, Yong-Kang ;
Akama, Tsutomu ;
Lau, Agnes ;
Zhou, Huchen ;
Hernandez, Vincent ;
Mao, Weimin ;
Alley, M. R. K. ;
Sanders, Virginia ;
Plattner, Jacob J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) :4447-4450