Heterocyclic Scaffolds I: ß-Lactams

385 Pages·2010·9.233 MB·English

by  Benito Alcaide, Pedro Almendros (auth.), Bimal K. Banik (eds.)

22
Topics in Heterocyclic Chemistry
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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.
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be pleased to receive suggestions and supplementary information. Papers are accepted for Topics
inHeterocyclicChemistryinEnglish.
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TopicsinHeterocyclicChemistryISSN1861-9282
ISBN978-3-642-12844-8 e-ISBN978-3-642-12845-5
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OrganicSynthesis
DepartmentofChemistry
UniversityofAntwerp
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UniversityofTexas-PanAmerican
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Prof.RyojiNoyoriNL Prof.AlbertPadwa
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RIKEN(TheInstituteofPhysical DepartmentofChemistry
andChemicalResearch) EmoryUniversity
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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.
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vii
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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
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