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Synthesis of the enantiomers of the dual function 2‐nitroimidazole radiation sensitizer RB 6145
dc.contributor.authorSercel, Anthony D.en_US
dc.contributor.authorBeylin, Vladimir G.en_US
dc.contributor.authorMarlatt, Mark E.en_US
dc.contributor.authorLeja, Boguslawaen_US
dc.contributor.authorShowalter, H. D. Hollisen_US
dc.contributor.authorMichel, Andréen_US
dc.date.accessioned2013-02-12T19:00:59Z
dc.date.available2013-02-12T19:00:59Z
dc.date.issued2006-11en_US
dc.identifier.citationSercel, Anthony D.; Beylin, Vladimir G.; Marlatt, Mark E.; Leja, Boguslawa; Showalter, H. D. Hollis; Michel, André (2006). "Synthesis of the enantiomers of the dual function 2â nitroimidazole radiation sensitizer RB 6145." Journal of Heterocyclic Chemistry 43(6): 1597-1604. <http://hdl.handle.net/2027.42/96351>en_US
dc.identifier.issn0022-152Xen_US
dc.identifier.issn1943-5193en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/96351
dc.description.abstractShort, efficient pathways are described for the synthesis of racemic 2‐nitroimidazole radiation sensitizer RB‐6145 ( 2a ) and each of its corresponding ( R )‐ and ( S )‐enantiomers ( 2b and 2c , respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3‐trimethylsilyl‐2‐oxazolidinone ( 3b ) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the ( R )‐enantiomer ( 2b ) has been successfully scaled up to provide multi‐kilo quantities of material for early stage preclinical evaluation.en_US
dc.publisherWiley‐Blackwellen_US
dc.titleSynthesis of the enantiomers of the dual function 2‐nitroimidazole radiation sensitizer RB 6145en_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelOrganic Chemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumCollege of Pharmacy, University of Michigan, Ann Arbor, MI 48109‐1065en_US
dc.contributor.affiliationotherChemistry Department and Chemical Research & Development, Pfizer Global Research and Development, Michigan Laboratories, Ann Arbor, MI 48105en_US
dc.contributor.affiliationotherChemistry Department, Université de Sherbrooke, Sherbrooke (Québec), Canada J1K 2R1en_US
dc.contributor.affiliationotherAureus Pharma, 75010 Paris, France; Tel: +33 (0) 1 40 18 57 57; Fax: +33 (0) 1 40 18 57 58en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/96351/1/5570430625_ftp.pdf
dc.identifier.doi10.1002/jhet.5570430625en_US
dc.identifier.sourceJournal of Heterocyclic Chemistryen_US
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dc.identifier.citedreferenceAll inquiries regarding X‐ray data of 2b should be directed to A. Michel.en_US
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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