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Spirocyclic β-Lactams: Synthesis and Biological Evaluation of Novel Heterocycles

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Heterocyclic Scaffolds I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 22))

Abstract

β-Lactam rings containing compounds are a group of antibiotics of unparalleled importance in chemotherapy. Considerable effort has been reported in the development of novel, more effective β-lactam compounds as well as their biological evaluation. This article reviews the progress made in the stereoselective synthesis of spiro-β-lactams, a unique class of heterocycles, their biological evaluation, and their applications in various related fields. The introductory paragraph highlights the significance of the β-lactam chemistry and is followed by an overview of monocyclic-, bicyclic-, and tricyclic-β-lactams. The other sections of the article deal with the stereoselective synthesis and biological evaluation of spiro-β-lactams, including their use as synthetic intermediates for β-turn mimics and β-turn nucleators. The potential of spiro-β-lactams as cholesterol absorption inhibitors, β-lactamase inhibitors, and antiviral, antibacterial, and antimicrobial agents has also been described.

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Abbreviations

Ac:

Acetyl

AIBN:

2,2′-Azobisisobutyronitrile

Ar:

Aryl

Bn:

Benzyl

Boc:

tert-Butoxycarbonyl

BSA:

N,O-Bis(trimethylsilyl)acetamide

Bu:

Butyl

t-Bu:

tert-Butyl

Cbz:

Benzyloxycarbonyl

d:

Day(s)

DCC:

N,N-Dicyclohexylcarbodiimide

de:

Diastereomeric excess

DEAD:

Diethyl azodicarboxylate

DIBALH:

Diisobutylaluminum hydride

DIPEA:

N,N-Diisopropylethylamine

DMAP:

4-(Dimethylamino)pyridine

DMF:

N,N-Dimethylformamide

DMSO:

Dimethyl sulfoxide

ee:

Enantiomeric excess

Et:

Ethyl

h:

Hour(s)

HATU:

O-(7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluranium tetrafluroborate

IR:

Infrared

KHMDS:

Potassium hexamethyldisilazide

LDA:

Lithium diisopropylamide

LHMDS:

Lithium hexamethyldisilazide

MCPBA:

m-Chloroperoxybenzoic acid

Me:

Methyl

MIC:

Minimal inhibitory concentration

min:

Minute(s)

mL:

Milliliter(s)

Ms:

Mesityl

NCS:

N-Chlorosuccinimide

NMP:

N-Methylpyrrolidone

NMR:

Nuclear magnetic resonance

NOE:

Nuclear overhauser effect

Nu:

Nucleophile

PCC:

Pyridinium chlorochromate

Ph:

Phenyl

i-Pr:

Isopropyl

PTC:

Phase transfer catalyst

p-TSA:

p-Toluenesulfonic acid

f:

Room temperature

TBAF:

Tetrabutylammonium fluoride

TBAI:

Tetrabutylammonium iodide

TCNE:

Tetracyanoethylene

TEA:

Triethylamine

THF:

Tetrahydrofuran

TMS:

Tetramethylsilane

Ts:

Tosyl

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Authors and Affiliations

  1. Department of Chemistry, Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160 014, India

    Shamsher S. Bari & Aman Bhalla

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  1. Shamsher S. Bari
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  2. Aman Bhalla
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Correspondence to Shamsher S. Bari .

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Editors and Affiliations

  1. Dept. Chemistry, University of Texas-Pan American, W. University Drive 1201, Edinburg, 78539, USA

    Bimal K. Banik

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Bari, S.S., Bhalla, A. (2010). Spirocyclic β-Lactams: Synthesis and Biological Evaluation of Novel Heterocycles. In: Banik, B. (eds) Heterocyclic Scaffolds I. Topics in Heterocyclic Chemistry, vol 22. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_8

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