Barrie E. Kirk
Research Triangle Park
21 Papers
404 Citations
Barrie E. Kirk is an academic researcher from Research Triangle Park. The author has contributed to research in topics: Squalene & Epoxide. The author has an hindex of 11, co-authored 21 publications.
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Papers
Synthesis and enzymatic resolution of carbocyclic 2′-ara-fluoro-guanosine: a potent new anti-herpetic agent
Alan D. Borthwick,Suzanne Butt,Keith Biggadike,Anne M. Exall,Stanley M. Roberts,Peter Youds,Barrie E. Kirk,Brian R. Booth,Janet M. Cameron,Susan W. Cox,Clara L.P. Marr,Mark D. Shill +11 more
TL;DR: Carbocyclic-9-(2′-deoxy-2′ −β-fluoroarabinofuranosyl) guanine (8) and the corresponding furanose compound (12) have been synthesized; the former compound [which was resolved by formation of the monophosphate (20) and enantioselective hydrolysis using a 5′-nucleotidase] is an extremely potent inhibitor of herpes simplex viruses types 1 and 2.
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Short convergent route to homochiral carbocyclic-2′-deoxynucleosides and carbocyclic ribonucleosides
Keith Biggadike,Alan D. Borthwick,Anne M. Exall,Barrie E. Kirk,Stanley M. Roberts,Peter Youds +5 more
TL;DR: The epoxide has been converted into the antiviral agents (5, 6, 7, and 8) and the epoxide furnished carbocyclic guanosine (12) as mentioned in this paper.
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Use of diethylaminosulphur trifluoride (DAST) in the preparation of synthons of carbocyclic nucleosides
Keith Biggadike,Alan D. Borthwick,Derek Evans,Anne M. Exall,Barrie E. Kirk,Stanley M. Roberts,Les Stephenson,Peter Youds +7 more
TL;DR: The effect of neighbouring groups on the course of some DAST reactions is discussed in this article, where the effect of neighboring groups on a DAST reaction is discussed as well as its effect on the synthesis of fluorocarbocyclic nucleosides.
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Fluoro carbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodouracil.
Alan D. Borthwick,Derek Evans,Barrie E. Kirk,Keith Biggadike,Anne M. Exall,Peter Youds,Stanley M. Roberts,D. J. Knight,Jonathan A. V. Coates +8 more
TL;DR: The racemic carbocyclic 2'-fluoroarabinosyl pyrimidine nucleosides 8, 9, 12, and 13 and the cytidine analogues 12 and 20 displayed modest activity in vitro againstHSV-1 and HSV-2 but were inactive against human influenza A virus.
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Fluorocarbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluorocarbocyclic 2'-deoxy guanosines.
Alan D. Borthwick,Barrie E. Kirk,Keith Biggadike,Anne M. Exall,S. Butt,Stanley M. Roberts,D. J. Knight,Jonathan Coates,D. M. Ryan +8 more
TL;DR: The 6' alpha-fluoro derivative 11d exhibited comparable activity to that of acyclovir (ACV) against herpes simplex virus type 1 (HSV-1) and type 2 (HSVs-2) in vitro but was greater than 30-fold more active than ACV against HSV-2 in vivo in the mouse systemic model.
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