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B.","year":"1974","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"3974","DOI":"10.1073\/pnas.77.7.3974","volume":"77","author":"McMurry L.","year":"1980","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"1648","DOI":"10.1128\/AAC.31.10.1648","volume":"31","author":"McMurry L.","year":"1987","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"564","DOI":"10.1128\/jb.165.2.564-569.1986","volume":"165","author":"Burdett V.","year":"1986","journal-title":"J. Bacteriol."},{"key":"ref7\/cit7b","doi-asserted-by":"crossref","first-page":"1218","DOI":"10.1093\/nar\/16.3.1218","volume":"16","author":"Sanchez-Pescador R.","year":"1988","journal-title":"Nucleic Acids Res."},{"key":"ref7\/cit7c","doi-asserted-by":"crossref","first-page":"3675","DOI":"10.1128\/AAC.47.12.3675-3681.2003","volume":"47","author":"Connell S. R.","year":"2003","journal-title":"Antimicrob. Agents Chemother."},{"issue":"6","key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1021\/jm00340a014","author":"Spencer J. L.","year":"1963","journal-title":"J. Med. Chem."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"2643","DOI":"10.1021\/ja00900a027","volume":"85","author":"Stephens C. R.","year":"1963","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8c","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1021\/jm00313a009","volume":"10","author":"Martell M. J.","year":"1967","journal-title":"J. Med. Chem."},{"key":"ref8\/cit8d","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1021\/jo00804a025","volume":"36","author":"Church R. F. R.","year":"1971","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1021\/jm00027a023","volume":"37","author":"Sum P.-E.","year":"1994","journal-title":"J. Med. Chem."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1358\/dot.2005.41.10.937460","volume":"41","author":"Jones C. H.","year":"2005","journal-title":"Drugs Today"},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1179\/joc.2008.20.Supplement-1.3","volume":"20","author":"French G. L.","year":"2008","journal-title":"J. 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Chem."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"3704","DOI":"10.1021\/jm1015395","volume":"54","author":"Sun C.","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"3674","DOI":"10.1021\/jo01057a501","volume":"27","author":"Hlavka J. J.","year":"1962","journal-title":"J. Org. Chem."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"256","DOI":"10.1093\/jac\/dkl224","volume":"58","author":"Agwuh K. N.","year":"2006","journal-title":"J. Antimicrob. Chemother."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"355","DOI":"10.2165\/00003088-198815060-00001","volume":"15","author":"Saivin S.","year":"1988","journal-title":"Clin. Pharmacokinet."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1002\/bdd.2510140610","volume":"14","author":"Cook H. J.","year":"1993","journal-title":"Biopharm. Drug Dispos."},{"key":"ref20\/cit20","unstructured":"Ronn, M.; Dunwoody, N.; Sutcliffe, J.Pharmacokinetics of TP-434 in mouse, rat, dog, monkey, and chimpanzee. Presented at the50th Interscience Conference on Antimicrobial Agents and Chemotherapy Conference,Boston, MA,September 12\u201315, 2010, paper F1\u20132163."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"2849","DOI":"10.1021\/ja01568a050","volume":"79","author":"McCormick J. R. D.","year":"1957","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22a","doi-asserted-by":"crossref","first-page":"1599","DOI":"10.1002\/adsc.200404216","volume":"346","author":"Schlummer B.","year":"2004","journal-title":"Adv. Synth. Catal."},{"key":"ref22\/cit22b","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/S0022-328X(98)01054-7","volume":"576","author":"Yang B. H.","year":"1999","journal-title":"J. Organomet. Chem."},{"key":"ref23\/cit23a","doi-asserted-by":"crossref","first-page":"1611","DOI":"10.1086\/652759","volume":"50","author":"Sengstock D. M.","year":"2010","journal-title":"Clin. Infect. Dis."},{"key":"ref23\/cit23b","doi-asserted-by":"crossref","first-page":"939","DOI":"10.1038\/nrmicro1789","volume":"5","author":"Dijkshoorn L.","year":"2007","journal-title":"Nature Rev. Microbiol."},{"key":"ref24\/cit24","unstructured":"Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically,8thed.Approved Standard M07-A8, Vol.29, no. 2;Clinical and Laboratory Standards Institute:Wayne, PA, 2009."},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1021\/jm201465w"}],"container-title":["Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jm201467r","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,14]],"date-time":"2023-04-14T07:48:12Z","timestamp":1681458492000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jm201467r"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,1,6]]},"references-count":45,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2012,1,26]]}},"alternative-id":["10.1021\/jm201467r"],"URL":"https:\/\/doi.org\/10.1021\/jm201467r","relation":{},"ISSN":["0022-2623","1520-4804"],"issn-type":[{"value":"0022-2623","type":"print"},{"value":"1520-4804","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,1,6]]}}}