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Recent Approaches Toward the Generation of Molecular Diversity Based on β-Lactam Structures

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Beta-Lactams

Abstract

One of the most significant strategies in the search of biologically promising structures is the generation of scaffold diversity. Varying molecular scaffolds yielded useful small molecule tools for chemical genetic studies of cellular protein functions, apart from “classic” drug discovery approaches. In this chapter, the latest developments for the transformation of β-lactam monocyclic moieties into complex and diverse structures are discussed. The significance of the 2-azetidinones as starting material for the synthesis of libraries of fused and non-fused multicyclic β-lactams, multicyclic (non-β-lactamic) scaffolds, as well as new heterocyclic derivatives of pyrroles, γ-lactones, γ-lactams, oxazinones, imidazolidines, piperazines, piperidines, among others. Finally, the importance of β-lactam-based hybrids as a new source of potential biologically active compounds, have been also highlighted.

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Abbreviations

Ac:

Acetyl

AIBN:

2,2′-azobisisobutyronitrile

Bn:

Benzyl

Bz:

Benzoyl

CAN:

Ceric ammonium nitrate

DCC:

N,N′-dicyclohexylcarbodiimide

DCE:

Dichloroethane

DIC:

N,N′-diisopropylcarbodiimide

DMF:

Dimethylformamide

DMS:

Dimethyl sulfide

HOBt:

1-hydroxybenzotriazole

MOM:

Methoxymethyl ether

Ms:

Mesityl

MW:

Microwave

NBS:

N-bromosuccinimide

NOE:

Nuclear Overhauser effect

Ph:

Phenyl

PMB:

p-methoxybenzyl

PMP:

p-methoxyphenyl

PTSA:

p-toluenesulfonic acid

TBAF:

Tetrabutylammonium fluoride

TBS:

tert-Butyldimethylsilyl

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

Ts:

Tosyl, 4-toluenesulfonyl

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Acknowledgements

We gratefully acknowledge financial support from Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT) and Universidad Nacional de Rosario, Argentina. M.M.A. thanks CONICET for fellowship.

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Authors and Affiliations

  1. Instituto de Química Rosario (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000, Rosario, Argentina

    Carina M.L. Delpiccolo, Maitena Martinez-Amezaga & Ernesto G. Mata

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  1. Carina M.L. Delpiccolo
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  2. Maitena Martinez-Amezaga
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  3. Ernesto G. Mata
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Correspondence to Ernesto G. Mata .

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  1. Community Health System of South Texas, Edinburg, Texas, USA

    Bimal K. Banik

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Delpiccolo, C.M., Martinez-Amezaga, M., Mata, E.G. (2017). Recent Approaches Toward the Generation of Molecular Diversity Based on β-Lactam Structures. In: Banik, B. (eds) Beta-Lactams. Springer, Cham. https://doi.org/10.1007/978-3-319-55621-5_5

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