Asymmetric Synthesis of a New Monocyclic β-Lactam as a potential biological active compound

Jarrahpour, Aliasghar; Jahaniani, A. R.

doi:10.3390/m439

Cited by 2 publications

(1 citation statement)

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“…The Schiff base obtained by (S)-(À)-tyrosine ethyl ester hydrochloride with 2-hydroxybenzaldehyde has been reported to be transformed, via Staudinger reaction, into the chiral monocyclic b-lactam by treatment with achiral ketene prepared in situ from phthaloylglycyl chloride and triethylamine [107]. Ketene-imine cycloaddition reactions of ethoxycarbonyl(phenylthio)ketene with various imines and subsequent desulfurization reactions have been reported in 2006 to synthesize 3-ethoxycarbonyl b-lactam derivatives [108].…”

Section: General Synthetic Methodologies Of B-lactam's Preparationmentioning

confidence: 99%

Novel and Recent Synthesis and Applications of β-Lactams

Troisi

Granito

Pindinelli

2010

Topics in Heterocyclic Chemistry

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In this chapter, a comprehensive overview of the most significant and interesting contributions published from 2000 until now, concerning the preparation of novel b-lactam structures is presented. Among the different synthetic strategies available, either novel or already known but efficient and versatile methodologies are covered. The simple modifications of one or more substituents linked to the nitrogen N-1, the C-3, and the C-4 carbon atoms of the b-lactam nucleus were considered as an alternative synthetic protocol of more complex and polyfunctionalized molecules. Indeed, it is well known and extensively reviewed that the biological activity of this strained four-membered heterocycle is strictly dependent on the nature of the substituent groups that affect the reactivity towards the molecular active sites, increasing or lowering the possibility of interaction with the substrates. Finally, a synthetic survey of the most significant biological and pharmacological applications of the 2-azetidinones is reported.

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Section: General Synthetic Methodologies Of B-lactam's Preparationmentioning

confidence: 99%