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Recent Approaches Toward Solid Phase Synthesis of β-Lactams

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Heterocyclic Scaffolds I

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

Abstract

Since the discovery of penicillin in 1929, β-lactam antibiotics have been recognized as potentially chemotherapeutic drugs of incomparable effectiveness, conjugating a broad spectrum of activity with very low toxicity. The primary motif azetidin-2-one ring (β-lactam) has been considered as specific pharmacophores and scaffolds. With the advent of combinatorial chemistry and automated parallel synthesis coupled with ample interests from the pharmaceutical industries, recent trends have been driven mostly by adopting solid phase techniques and polymer-supported synthesis of β-lactams. The present survey will present an overview of the developments on the polymer-supported and solid phase techniques for the preparation of β-lactam ring or β-lactam containing antibiotics published over the last decade. Both unsubstituted and substitutions with different functional groups at various positions of β-lactams have been synthesized using solid phase technology. However, Wang resin and application of Staudinger [2+2] cycloaddition reaction have remained hitherto the major choice. It may be expected that other solid phase approaches involving different resins would be developed in the coming years.

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Abbreviations

AM-resin:

Aminomethylated polystyrene

BAL:

Backbone amide linker

BEMP resin:

Resin 2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro- 1,3,2-diazaphosphorine immobilized on polystyrene resin

BOBA:

Benzyloxybenzyl amine

BQ:

Benzoylquinine

CAN:

Cerric ammonium nitrate

DCC:

N,N′-Dicyclo-hexylcarbodiimide

DEAD:

Diethylazodicarboxylate

DIPEA:

Diisopropylethyl amine

DMAP:

4-Dimethylaminopyridine

DMF:

N,N-Dimethylformamide

DMTMM:

(4,6-Dimethoxy-[1,3,5]-triazin-2-yl)-4-methyl-morpholinium chloride

EDC:

N-Ethyl-N′-[3-(dimethylamino)propyl]-carbodiimide hydrochloride

FDPP:

Pentafluoro phenyldiphenyl phosphate

Fmoc:

9-Fluorenylmethoxycarbonyl

HOBt:

Hydroxybenzotriazol

LiHMDS:

Lithium hexamethyldisilazane

MAMP:

Merrifield, alpha methoxy phenyl resin

MCPBA:

m-Chloroperbenzoic acid

MeOPEG:

Methoxy polyethylene glycol

NCA:

N-Carboxy α-aminoacid anhydride

NMP:

N-Methylpyrrolidone

PAL:

Peptide amide linker

PASP:

Polymer assisted solution phase

PBP:

Penicillin-binding proteins

PEG:

Polyethylene glycol

SASRIN:

Super acid sensitive resin

TEA:

Triethylamine

TFA:

Trifluoroacetic acid

TMAD:

Tetramethylamine azodicarboxylate.

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Acknowledgments

Partial financial support from the Department of Science & Technology, New Delhi, India (Grant No. SR/S1/OC–49/2006) is gratefully acknowledged. BM thanks CSIR, New Delhi for Senior Research Fellowship.

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  1. Department of Chemistry, North Bengal University, Darjeeling, 734 013, India

    Bablee Mandal, Pranab Ghosh & Basudeb Basu

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  1. Bablee Mandal
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  2. Pranab Ghosh
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  3. Basudeb Basu
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Correspondence to Basudeb Basu .

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

    Bimal K. Banik

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Mandal, B., Ghosh, P., Basu, B. (2010). Recent Approaches Toward Solid Phase Synthesis of β-Lactams. In: Banik, B. (eds) Heterocyclic Scaffolds I. Topics in Heterocyclic Chemistry, vol 22. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_9

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