Boron Medicinal Chemistry and Synthetic Aspects

Abstract

Future Medicinal ChemistryVol. 5, No. 6 EditorialBoron medicinal chemistry and synthetic aspectsJonathan T Ahmet & John SpencerJonathan T AhmetDepartment of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, East Sussex, BN1 9QJ, UKSearch for more papers by this author & John Spencer* Author for correspondenceDepartment of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, East Sussex, BN1 9QJ, UK. Search for more papers by this authorEmail the corresponding author at j.spencer@sussex.ac.ukPublished Online:25 Apr 2013https://doi.org/10.4155/fmc.13.40AboutSectionsView ArticleView Full TextPDF/EPUB ToolsAdd to favoritesDownload CitationsTrack CitationsPermissionsReprints ShareShare onFacebookTwitterLinkedInReddit View article"Boron medicinal chemistry and synthetic aspects." , 5(6), pp. 621–622Keywords: anticancer agentsbiosensorsC-C bond couplingenzyme inhibitorsReferences1 Hall DG, Ishiyama T, Miyaura N et al. Boronic Acids – Preparation and Applications in Organic Synthesis and Medicine. Hall DG (Ed.). Wiley-VCH, Weinheim, Germany (2005).Google Scholar2 Trippier PC, McGuigan C. Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications. Med. Chem. Commun.1,183–198 (2010).Crossref, CAS, Google Scholar3 Miyaura N, Yanagi T, Suzuki A. The palladium – catalyzed cross-coupling reactions of phenylboronic acid with haloarenes in the presence of bases. Synth. Commun.11,513–519 (1981).Crossref, CAS, Google Scholar4 Del Valle L, Stille JK, Hegedus LS. Palladium-catalyzed coupling of allylic acetates with aryl- and vinylstannanes. J. Org. Chem.55(10),3019–3023 (1990).Crossref, CAS, Google Scholar5 Matteson DS. Alpha-halo boronic esters: intermediates for stereodirected synthesis. Chem. Rev.89,1535–1551 (1989).Crossref, CAS, Google Scholar6 Gillis EP, Burke MD. Multistep synthesis of complex boronic acids from simple MIDA boronates. J. Am. Chem. Soc.130,14084–14085 (2008).Crossref, Medline, CAS, Google Scholar7 Robbins DW, Hartwig JW. Sterically controlled alkylation of arenes through iridium-catalyzed C-H borylation. Angew. Chem. Int. Ed. Engl.52,933–937 (2013).Crossref, Medline, CAS, Google Scholar8 Gutekunst WR, Baran PS. C-H functionalization logic in total synthesis. Chem. Soc. Rev.40,1976–1991 (2011).Crossref, Medline, CAS, Google Scholar9 Chen X, Schauder S, Potier N et al. Structural identification of a bacterial quorum-sensing signal containing boron. Nature415(6871),545–549 (2002).Crossref, Medline, CAS, Google Scholar10 Hutter R, Keller-Schierlein W, Knusel F et al. The metabolic products of microorganisms. Boromycin. Helv. Chim. Acta.50(6),1533–1539 (1967).Crossref, Medline, CAS, Google Scholar11 Dembitsky VM, Al-Quntar AAA, Srebnik M. Natural and synthetic small boron-containing molecules as potential inhibitors of bacterial and fungal quorum sensing. Chem. Rev.111,209–237 (2011).Crossref, Medline, CAS, Google Scholar12 Smoum R, Rubinstein A, Dembitsky VM, Srebnik M. Boron containing compounds as protease inhibitors. Chem. Rev.112(7),4156–4220 (2012).Crossref, Medline, CAS, Google Scholar13 Touchet S, Carreaux F, Carboni B, Bouillon AL, Boucher JL. Iridium-catalyzed allylic amination route to α-aminoboronates: illustration of the decisive role of boron substituents. Chem. Soc. Rev.40,3895–3914 (2011).Crossref, Medline, CAS, Google Scholar14 Bross PF, Kane R, Farrell AT et al. Approval summary for bortezomib for injection in the treatment of multiple myeloma. Clin. Cancer Res.10(12),3954–3964 (2004).Crossref, Medline, CAS, Google Scholar15 Baker SJ, Tomsho JW, Benkovic SJ. Boron-containing inhibitors of synthetases. Chem. Soc. Rev.40(8),4279–4285 (2011).Crossref, Medline, CAS, Google Scholar16 Geninatti Crich S, Alberti D, Szabo I, Aime S, Djanashvili K. MRI visualization of melanoma cells by targeting overexpressed sialic acid with a GdIII-dota-en-pba imaging reporter. Angew. Chem. Int. Ed. Engl.52,1161–1164 (2013).Crossref, Medline, CAS, Google Scholar17 Van de Bittner GC, Bertozzi CR, Chang CJ. Strategy for dual-analyte luciferin imaging: in vivo bioluminescence detection of hydrogen peroxide and caspase activity in a murine model of acute inflammation. J. Am. Chem. Soc.135,1783–1795 (2013).Crossref, Medline, CAS, Google Scholar18 Brown HC. Organic syntheses via boranes. John Wiley and Sons, Inc., NY, USA (1975).Google ScholarFiguresReferencesRelatedDetailsCited BySynthesis and antimicrobial properties of cyclic fluorodiamines containing boronate esters20 November 2017 | Heteroatom Chemistry, Vol. 28, No. 6Synthesis, characterization, and anticancer properties of iminophosphineplatinum(II) complexes containing boronate estersCanadian Journal of Chemistry, Vol. 95, No. 2Synthesis, Characterization, and Anticancer Activities of Pyrogallol-Based Arylspiroborates27 July 2015 | Journal of Heterocyclic Chemistry, Vol. 53, No. 6ChemInform Abstract: Boron Medicinal Chemistry and Synthetic Aspects1 July 2013 | ChemInform, Vol. 44, No. 29Focusing on boron in medicinal chemistryP Veeraraghavan Ramachandran25 April 2013 | Future Medicinal Chemistry, Vol. 5, No. 6 Vol. 5, No. 6 Follow us on social media for the latest updates Metrics Downloaded 170 times History Published online 25 April 2013 Published in print April 2013 Information© Future Science LtdKeywordsanticancer agentsbiosensorsC-C bond couplingenzyme inhibitorsFinancial & competing interests disclosureThe authors have no relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.No writing assistance was utilized in the production of this manuscript.PDF download