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Novel Anticancer β-Lactams

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Heterocyclic Scaffolds I

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

Abstract

Stereocontrolled synthesis of racemic and chiral novel β-lactams using polyaromatic imines has been accomplished. Domestic and automated microwave-induced reactions have been investigated for the preparation of these types of β-lactams. A preliminary mechanism of this reaction has been advanced. Formation of trans-β-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride with imines in the presence of tertiary base. A donor–acceptor complex pathway has been believed to be involved in the formation of cis-β-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the β-lactams. Structure–activity relationship has identified β-lactams with anticancer activity. The presence of an acetoxy group has proven very important for anticancer activity. The preparation and mechanism of action of several other new anticancer β-lactams have also been explored.

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Abbreviations

DMF:

Dimethyl formamide

DMSO:

Dimethyl sulfoxide

DNA:

Deoxyribonucleic acid

h:

Hour (s)

IC50 :

Cell growth inhibition at 50% concentration

NMR:

Nuclear magnetic resonance

PAH:

Polyaromatic hydrocarbon

SN2 :

Substitution nucleophilic bimolecular

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Acknowledgment

We gratefully acknowledge the financial support for this research project from National Institutes of Health-SCORE (2S06M008038-39).

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Authors and Affiliations

  1. Department of Chemistry, The University of Texas Pan American, 1201 West University Drive, Edinburg, TX, 78539, USA

    Bimal K. Banik

  2. Department of Molecular Pathology, Unit 951, The University of Texas M. D. Anderson Cancer Center, 7435 Fannin Street, Houston, TX, 77504, USA

    Indrani Banik & Frederick F. Becker

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  1. Bimal K. Banik
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  2. Indrani Banik
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Correspondence to Bimal K. Banik .

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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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Banik, B.K., Banik, I., Becker, F.F. (2010). Novel Anticancer β-Lactams. In: Banik, B. (eds) Heterocyclic Scaffolds I. Topics in Heterocyclic Chemistry, vol 22. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_28

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