Heterocyclic Scaffolds I: ß-Lactams PDF
Preview Heterocyclic Scaffolds I: ß-Lactams
22 Topics in Heterocyclic Chemistry Series Editor: Bert U. W. Maes Editorial Board: D. Enders S.V. Ley G. Mehta K.C. Nicolaou l l l l R. Noyori L.E. Overman A. Padwa S. Polanc l l l Topics in Heterocyclic Chemistry SeriesEditor:BertU.W.Maes RecentlyPublishedandForthcomingVolumes SynthesisofHeterocyclesvia SynthesisofHeterocyclesvia MulticomponentReactionsI CycloadditionsI VolumeEditors:R.V.A.Orru,E.Ruijter VolumeEditor:A.Hassner Volume23,2010 Volume12,2008 HeterocyclicScaffoldsI:b-Lactams BioactiveHeterocyclesV VolumeEditor:M.T.H.Khan VolumeEditor:B.Banik Volume11,2007 Volume22,2010 BioactiveHeterocyclesIV PhosphorousHeterocyclesII VolumeEditor:M.T.H.Khan VolumeEditor:R.K.Bansal Volume10,2007 Volume21,2010 BioactiveHeterocyclesIII PhosphorousHeterocyclesI VolumeEditor:M.T.H.Khan VolumeEditor:R.K.Bansal Volume9,2007 Volume20,2009 BioactiveHeterocyclesII VolumeEditor:S.Eguchi AromaticityinHeterocyclicCompounds Volume8,2007 VolumeEditors:T.Krygowski,M.Cyran´ski Volume19,2009 HeterocyclesfromCarbohydrate Precursors HeterocyclicSupramoleculesI VolumeEditor:E.S.H.ElAshry VolumeEditor:K.Matsumoto Volume7,2007 Volume17,2008 BioactiveHeterocyclesI BioactiveHeterocyclesVI VolumeEditor:S.Eguchi FlavonoidsandAnthocyaninsinPlants, Volume6,2006 andLatestBioactiveHeterocyclesI VolumeEditor:N.Motohashi MarineNaturalProducts Volume15,2008 VolumeEditor:H.Kiyota Volume5,2006 HeterocyclicPolymethineDyes QSARandMolecularModelingStudiesin Synthesis,PropertiesandApplications HeterocyclicDrugsII VolumeEditor:L.Strekowski VolumeEditor:S.P.Gupta Volume14,2008 Volume4,2006 SynthesisofHeterocyclesvia QSARandMolecularModelingStudiesin CycloadditionsII HeterocyclicDrugsI VolumeEditor:A.Hassner VolumeEditor:S.P.Gupta Volume13,2008 Volume3,2006 Heterocyclic Scaffolds I b -Lactams Volume Editor: Bimal K. Banik With contributions by (cid:1) (cid:1) (cid:1) (cid:1) B. Alcaide P. Almendros A. Arrieta B.K. Banik (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) I. Banik S.S. Bari B. Basu F.F. Becker A. Bhalla F.P. Coss´ıo (cid:1) P. Ghosh (cid:1) C. Granito (cid:1) B. Lecea (cid:1) B. Mandal (cid:1) (cid:1) (cid:1) (cid:1) M. Oiarbide C. Palomo E. Pindinelli L. Troisi TheseriesTopicsin HeterocyclicChemistrypresentscriticalreviewson“HeterocyclicCompounds” withintopic-relatedvolumesdealingwithallaspectssuchassynthesis,reactionmechanisms,structure complexity, properties, reactivity, stability, fundamental and theoretical studies, biology, biomedical studies,pharmacologicalaspects,applicationsinmaterialsciences,etc.Metabolismwillalsobeincluded whichwillprovideinformationusefulindesigningpharmacologicallyactiveagents.Pathwaysinvolving destructionofheterocyclicringswillalsobedealtwithsothatsynthesisofspecificallyfunctionalized non-heterocyclicmoleculescanbedesigned. Theoverallscopeistocovertopicsdealingwithmostoftheareasofcurrenttrendsinheterocyclic chemistrywhichwillsuittoalargerheterocycliccommunity. Asarule,contributionsarespeciallycommissioned.Theeditorsandpublisherswill,however,always be pleased to receive suggestions and supplementary information. Papers are accepted for Topics inHeterocyclicChemistryinEnglish. In references, Topics in Heterocyclic Chemistry is abbreviated Top Heterocycl Chem and is cited asajournal. Springerwwwhomepage:springer.com VisittheTHCcontentatspringerlink.com TopicsinHeterocyclicChemistryISSN1861-9282 ISBN978-3-642-12844-8 e-ISBN978-3-642-12845-5 DOI10.1007/978-3-642-12845-5 SpringerHeidelbergDordrechtLondonNewYork LibraryofCongressControlNumber:2010927759 #Springer-VerlagBerlinHeidelberg2010 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting, reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationofthispublication orpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLawofSeptember9, 1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfromSpringer.Violations areliabletoprosecutionundertheGermanCopyrightLaw. Theuseofgeneraldescriptivenames,registerednames,trademarks,etc.inthispublicationdoesnot imply, even in the absence of a specific statement, that such names are exempt from the relevant protectivelawsandregulationsandthereforefreeforgeneraluse. Coverdesign:WMXDesignGmbH,Heidelberg,Germany Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Series Editor Prof.Dr.BertU.W.Maes OrganicSynthesis DepartmentofChemistry UniversityofAntwerp Groenenborgerlaan171 B-2020Antwerp Belgium Volume Editor Prof.BimalK.Banik UniversityofTexas-PanAmerican DepartmentofChemistry W.UniversityDrive1201 78539EdinburgTexas USA [email protected] Editorial Board Prof.D.Enders Prof.K.C.Nicolaou RWTHAachen Chairman Institutfu¨rOrganischeChemie DepartmentofChemistry 52074,Aachen,Germany TheScrippsResearchInstitute [email protected] 10550N.TorreyPinesRd. LaJolla,CA92037,USA Prof.StevenV.LeyFRS [email protected] and BP1702Professor ProfessorofChemistry andHeadofOrganicChemistry DepartmentofChemistryandBiochemistry UniversityofCambridge UniversityofCA DepartmentofChemistry SanDiego,9500GilmanDrive LensfieldRoad LaJolla,CA92093,USA Cambridge,CB21EW,UK [email protected] Prof.G.MehtaFRS Director DepartmentofOrganicChemistry IndianInstituteofScience Bangalore560012,India [email protected] vi EditorialBoard Prof.RyojiNoyoriNL Prof.AlbertPadwa President WilliamP.TimmieProfessorofChemistry RIKEN(TheInstituteofPhysical DepartmentofChemistry andChemicalResearch) EmoryUniversity 2-1Hirosawa,Wako Atlanta,GA30322,USA Saitama351-0198,Japan [email protected] and UniversityProfessor Prof.SlovenkoPolanc DepartmentofChemistry ProfessorofOrganicChemistry NagoyaUniversity FacultyofChemistryandChemical Chikusa,Nagoya464-8602,Japan Technology [email protected] UniversityofLjubljana Askerceva5 Prof.LarryE.Overman SI-1000Ljubljana DistinguishedProfessor Slovenia DepartmentofChemistry [email protected] 516RowlandHall UniversityofCalifornia,Irvine Irvine,CA92697-2025 [email protected] Topics in Heterocyclic Chemistry Also Available Electronically TopicsinHeterocyclicChemistryisincludedinSpringer’seBookpackageChemistry and Materials Science. If a library does not opt for the whole package the book series may be bought on a subscription basis. Also, all back volumes are available electronically. For all customers who have a standing order to the print version of Topics in Heterocyclic Chemistry, we offer the electronic version via SpringerLink free of charge. Ifyoudonothaveaccess,youcanstillviewthetableofcontentsofeachvolume andtheabstractofeacharticlebygoingtotheSpringerLinkhomepage,clickingon “Chemistry and Materials Science,” under Subject Collection, then “Book Series,” underContentTypeandfinallybyselectingTopicsinHeterocyclicChemistry. Youwillfindinformationaboutthe –EditorialBoard –AimsandScope –InstructionsforAuthors –SampleContribution at springer.com using the search function by typing in Topics in Heterocyclic Chemistry. ColorfiguresarepublishedinfullcolorintheelectronicversiononSpringerLink. Aims and Scope The series Topics in Heterocyclic Chemistry presents critical reviews on “Heterocyclic Compounds” within topic related volumes dealing with all aspects suchassynthesis,reactionmechanisms,structurecomplexity,properties,reactivity, stability, fundamental and theoretical studies, biology, biomedical studies, pharma- cologicalaspects,applicationsinmaterialsciencesetc.Metabolismisalsoincluded which provides information useful in designing pharmacologically active agents. Pathways involving destruction of heterocyclic ring are also dealt with so that synthesisofspecificallyfunctionalizednon-heterocyclicmoleculescanbedesigned. Overallscopeistocovertopicsdealingwithmostoftheareasofcurrenttrendsin heterocyclicchemistrywhichsuitsalargerheterocycliccommunity. The individual volumes of Topics in Heterocyclic Chemistry are thematic. Reviewarticlesaregenerallyinvitedbythevolumeeditors. In references Topics in Heterocyclic Chemistry is abbreviated Top Heterocycl Chemandiscitedasajournal. vii . Preface The significance of the stereocontrolled synthesis of chiral and achiral b-lactams with their mechanism of formation has gained attention in connection with the structure–activity relationship study and the development of b-lactam antibiotics, b-lactam anticancer agents, cholesterol-lowering drugs, nitrogen-containing hete- rocycles and inhibitors of b-lactamases. However, b-lactam antibiotics have still occupiedamajorroleinthetreatmentagainstpathogenicbacteriaandthusimprove inqualityofhumanlife.But,theextensiveuseofcommonb-lactamantibiotics(e.g., penicillinsandcephalosporins)inmedicinehascreatedsevereobstaclesbecauseof anincreasingnumberofresistantstrainsofbacteriathroughmutationandb-lacta- masegenetransfer.Duetotheincreasedbacterialaswellastumorcellresistance, there has been enormous effort devoted to prepare new structural types of com- pounds having the 2-azetidinone ring as a common feature. The diversity of this bookbySpringer“HeterocyclicScaffoldsI:b-Lactams”in“TopicsinHeterocyclic Chemistry”isconfirmedinthewiderangeofsignificanttopicswrittenbyexpertsin thisfield. Each one of the seven chapters presented in this book has focused on the very recent aspects in the b-lactam research. Alcaide and Almendros as well as Bari and Bhalla have described very powerfulstrategies for the preparation of unusual spirocyclic b-lactams. Troisi et al. and Palomo and Oiarbide have described the synthesis and application of b-lactams for the preparation of nitrogen-containing molecules.Basuetal.describethepreparationofb-lactamsusingsolid-supported reagents.Cossio’sgrouphasstudiedcomputationalapproachtoidentifythemecha- nistic routes on the synthesis of a variety of b-lactams. Development of novel anticancerb-lactamsalongwiththeir mechanismsofaction hasbeen provided by ourgroup. I take this opportunity to sincerely thank and congratulate the authors for their verysignificantandusefulcontribution.Thisbookprovidesadeeperunderstanding of the art of b-lactam research to the chemists, biologists, pharmacologists, and cliniciansatindustrialand/oracademicresearchinstitutionsthroughouttheworld. Edinburg,TexasTX,USA BimalK.Banik April2010 ix .
The list of books you might like
