Novel and Recent Synthesis and Applications of β-Lactams

  • Luigino Troisi
  • Catia Granito
  • Emanuela Pindinelli
Chapter
First Online:
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 22)

Abstract

In this chapter, a comprehensive overview of the most significant and interesting contributions published from 2000 until now, concerning the preparation of novel β-lactam structures is presented. Among the different synthetic strategies available, either novel or already known but efficient and versatile methodologies are covered. The simple modifications of one or more substituents linked to the nitrogen N-1, the C-3, and the C-4 carbon atoms of the β-lactam nucleus were considered as an alternative synthetic protocol of more complex and polyfunctionalized molecules. Indeed, it is well known and extensively reviewed that the biological activity of this strained four-membered heterocycle is strictly dependent on the nature of the substituent groups that affect the reactivity towards the molecular active sites, increasing or lowering the possibility of interaction with the substrates. Finally, a synthetic survey of the most significant biological and pharmacological applications of the 2-azetidinones is reported.

Keywords

Beta-lactam Cyclization reaction Enzyme inhibitor 

Abbreviations

ACAT

Acyl coenzyme A cholesterol transferases

Bn

Benzyl

Boc

tert-butoxycarbonyl

bpy

2,2′-bipyridyl

BQ

Benzoylquinine

BSA

Bis-trimethylsilylacetamide

BTPP

tert-butylimino-tri(pyrrolidino)phosphorane

n-BuLi

normal-butyllithium

s-BuLi

sec-butyllithium

CAD

Coronary artery disease

CAI

Cholesterol absorption inhibitor

CAIBP

Cholesterol absorption inhibitor binding protein

Cbz

Benzyloxycarbonyl

CH3OTf

Methyl triflate

CNS

Central nervous system

CSI

Chlorosulfonyl isocyanate

DABCO

1,4-diazabicyclo[2.2.2]octane

DBU

1,8-diazabicyclo[5.4.0]undec-7-ene

DCC

Dicyclohexylcarbodiimide

DEAD

Diethyl azodicarboxylate

DIPEA

N,N-diisopropylethylamine

DME

1,2-dimethoxyethane

DMF

N,N-dimethylformamide

DMSO

Dimethyl sulfoxide

ECM

Extracellular matrix

EDG

Electron-donating group

EWG

Electron-withdrawing group

Fmoc

9-fluorenylmethoxycarbonyl

GPCR

G protein-coupled receptor

HCMV

Human cytomegalovirus

HIU

High intensity ultrasound

HLE

Human leukocyte elastase

HMDA

Hexamethylendiamine

LDA

Lithium diisopropylamide

LE

Leukocyte elastase

LHMDS

Lithium bis(trimethylsilyl)amide

MCBA

meta-chloroperbenzoic acid

MMP

Matrix metalloproteinase

MMPP

Magnesium monoperoxyphthalate

MRSA

Methicillin-resistant Staphylococcus aureus

MW

Microwave

NMP

N-methylpyrrolidone

NMR

Nuclear magnetic resonance

OMP

ortho-methoxyphenyl

PBP

Penicillin-binding proteins

Pmb

para-methoxybenzaldehyde

PMN

Polymorphonuclear

PMP

para-methoxyphenyl

PPE

Porcine pancreatic elastase

PPY

4-(pyrrolidino)pyridine

SAR

Structure-activity relationship

SET

Single-electron-transfer

TBAF

Tetrabutylammonium fluoride

TBDMSCl

tert-butyl dimethylsilyl chloride

TBS

tert-butyldimethylsilyl

TFA

Trifluoroacetic acid

TIPS

Triisopropylsilyl

TMEDA

N,N,N′,N′-tetramethyl-1,2-ethylenediamine

TMSCl

Trimethylsilyl chloride

TPA

Tripyridylamine

TS

Transition state

Ts

Tosyl, 4-toluenesulfonyl

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Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Luigino Troisi
    • 1
  • Catia Granito
    • 1
  • Emanuela Pindinelli
    • 1
  1. 1.Dipartimento di Scienze e Tecnologie Biologiche ed AmbientaliUniversity of SalentoLecceItaly

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