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Beta-Lactams pp 1–39Cite as

Synthesis of Diverse β-Lactams: Role of Appended Hetero Moiety on Its Activity

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Abstract

β-Lactam, a four membered ring, found in the core structure of large number of clinically used antibiotics and served as synthon for the synthesis of amino acids, alkaloids and taxoids. Their biological behaviour of β-lactam is derived from its unique structure and reactivity. Monocyclic β-lactams, one of its major classes is popular due their wide range of pharmacological applications and the recent interest in this field is towards the monocyclic β-lactams appended with hetero moieties. In this regard, this chapter reviews the recent progress, particularly in the last 5 years, made in the synthesis of diverse hetrocyclic β-lactams and the role of appended hetero moieties on enhancing their biological aspects. The introductory part highlights the significance of β-lactam antibiotics and is followed by an overview of biologically active monocyclic-β-lactams. The other sections of chapter deal with the importance and recently developed methodologies for the synthesis of variety of heterocyclic β-lactams. Further, the biological potentials of novel heterocyclic β-lactams have also been described.

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Abbreviations

Å:

Angstrom

Ac:

Acetyl

Ar:

Aryl

iBu:

iso-Butyl

Bz/Bn:

Benzyl

[bmIm]:

1-Butyl-3-methylimidazolium

c-hex:

Cyclohexyl

c-hep:

Cycloheptyl

°C:

Degree centigrade

CAC:

Chloroacetyl chloride

CNS:

Central nervous system

CHCl3 :

Chloroform

DCC:

N,N-Dicyclohexylcarbodiimide

DCM:

Dichloromethane

DMF:

N,N-Dimethylformamide

DMSO:

Dimethylsulfoxide

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

ERGs:

Electron releasing groups

G:

Gram

GST:

Glutathione-S-transferase

H:

Hour

HLE:

Human leukocyte elastase

HOBt:

Hydroxybenzotriazole

MAOS:

Microwave assisted organic synthesis

MeOH:

Methyl alcohol

MWI:

Microwave irradiation

Μg:

Microgram

MIC:

Minimum inhibitory concentration

Min:

Minute

mL:

Millilitre

Mmol:

Millimole

MRSA:

Methicillin-resistant Staphylococcus aureus

MTT:

3-(4′,5′-dimethylthiazol-2′-yl)-2,5-diphenyltetrazolium bromide

Ph:

Phenyl

PMP:

p-Methoxyphenyl

POCl3 :

Phosphorous oxychloride

iPr:

iso-propyl

PTZ:

Pentylenetetrazole

TEA:

Triethylamine

THF:

Tetrahydrofuran

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Acknowledgements

We would like to apologize to those scientists whose work may not have appeared in this review either due to the limited scope of the review or oversight. We gratefully acknowledge the financial support for our heterocyclic β-lactam research programme from Department of Science and Technology (DST), New Delhi, Government of India, Project No. SR/FT/CS-037/2010 dated 28-10-2010, and University Grants Commission (UGC), India, vide sanction No. F.17-7(J)/2004 (SA-I) dated 03-10-2011.

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Authors and Affiliations

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

    Aman Bhalla, Shamsher S. Bari & Jitender Bhalla

Authors
  1. Aman Bhalla
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  2. Shamsher S. Bari
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  3. Jitender Bhalla
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Correspondence to Aman Bhalla .

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Editors and Affiliations

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

    Bimal K. Banik

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Bhalla, A., Bari, S.S., Bhalla, J. (2017). Synthesis of Diverse β-Lactams: Role of Appended Hetero Moiety on Its Activity. In: Banik, B. (eds) Beta-Lactams. Springer, Cham. https://doi.org/10.1007/978-3-319-55621-5_1

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