Penicillins

Marchand‐Brynaert, Jacqueline; Brulé, Cédric

doi:10.1016/b978-008044992-0.00203-0

Cited by 18 publications

(7 citation statements)

References 453 publications

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“…We focus instead on some of the most relevant reactions [181,222]. The most important transformation for the amino function in penicillins and cephalosporins is the protection, which is introduced in general as amide by acylating the 6-APA or 7-ACA [223].…”

Section: Reactions For the Transformation Of Functional Groups In Sidmentioning

confidence: 99%

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The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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The large number of recent reports on b-lactam chemistry demonstrates the increasing interest in this important class of compounds. Monocyclic b-lactams frequently serve as precursors for the synthesis of classical bicyclic b-lactam antibiotics. The cyclic 2-azetidinone skeleton has been extensively used as a template on which to build the heterocyclic structure fused to the four-membered ring, using the chirality and functionalization of the b-lactam nucleus as a stereocontrolling element. The discovery of nonclassical b-lactam antibiotics, such as monobactams and nocardicins, coupled with ever-growing new applications such as enzyme inhibition has triggered a renewed interest in the building of new monocyclic b-lactam derivatives. Besides the utility of b-lactams as biologically active agents, they are used as intermediates in a-and b-amino acid synthesis, as well as building blocks for alkaloids, heterocycles, taxoids and other types of compounds of biological and medicinal interest. Physicochemical Data Computational ChemistryTheoretical studies show that b-lactams are weaker bases, in the gas phase, than acyclic amides [1]. The attenuation of basicity upon cyclization is stronger than that found for cyclic ketones of similar size due to the existence of a negative hyperconjugation effect that is present in b-lactams but not in cyclic ketones. Ab initio calculations indicate that both b-lactams and acyclic amides are oxygen bases, but the gap between the oxygen and nitrogen intrinsic basicities is much smaller in the former due to the aforementioned cyclization effects. This decrease of the oxygen Modern Heterocyclic Chemistry, First Edition. Edited

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Section: Reactions For the Transformation Of Functional Groups In Sidmentioning

confidence: 99%

“…The antibacterial effect of b-lactam antibiotics such as penicillins (70) and cephalosporins (71) is due to their capacity to disrupt bacterial cell wall biosynthesis [181]. This is achieved by the antibiotics acting as inhibitors of penicillin binding proteins (PBPs), which are membrane bound serine peptidases.…”

Section: Introductionmentioning

confidence: 99%

The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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“…The 2-azetidinone ring (b-lactam) as a synthetic intermediate has been widely recognized in organic synthesis. It is an active moiety present in most widely used antibiotics, such as penicillins [13], cephalosporins [14], carbapenems [15], nocardicins [16] and monobactams [17]. Moreover, it showed many other interesting biological properties, such as cholesterol absorption inhibitors [18], human cytomegalovirus protease inhibitors [19], thrombin inhibitors [20], anti-hyperglycemic [21], anti-tumour [22], anti-HIV [23], anti-inflammatory, analgesic activities [24] and serine-dependent enzyme inhibitors [25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-formylated β-lactams using nano-sulfated TiO2 as catalyst under solvent-free conditions

Hosseini‐Sarvari

Safary

Jarrahpour

et al. 2012

Comptes Rendus. Chimie

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“…The 2-azetidinone template (β-lactam) has been widely described as a lead structure for the inhibition of serine hydrolases such as human leukocyte elastase (HLE), prostate specific antigen (PSA), thrombin, human cytomegalovirus, and mainly d , d -peptidases and β-lactamases, the bacterial target-enzymes of penicillin-type drugs used in antibiotherapy . Generally, enzyme inhibition results from the interaction between the 2-azetidinone carbonyl and the active serine of the catalytic triad Ser-His-Asp.…”

Section: Introductionmentioning

confidence: 99%

β-Lactams Derived from a Carbapenem Chiron Are Selective Inhibitors of Human Fatty Acid Amide Hydrolase versus Human Monoacylglycerol Lipase

et al. 2009

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A library of 30 beta-lactams has been prepared from (3R,4R)-3-[(R)-1'-(tbutyldimethylsilyloxy)-ethyl]-4-acetoxy-2-azetidinone, and the corresponding deacetoxy derivative, by sequential N- and O-functionalizations with various omega-alkenoyl and omega-arylalkanoyl chains. All compounds were selective inhibitors of hFAAH versus hMGL, and IC(50) values in the nanomolar range (5-14 nM) were recorded for the best representatives. From time-dependent preincubation and rapid dilution studies, and from docking analyses in a homology model of the target enzyme, a reversible mechanism of inhibition of hFAAH is proposed.

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Penicillins

Cited by 18 publications

References 453 publications

The Chemistry of 2‐Azetidinones (β‐Lactams)

The Chemistry of 2‐Azetidinones (β‐Lactams)

Synthesis of N-formylated β-lactams using nano-sulfated TiO2 as catalyst under solvent-free conditions

β-Lactams Derived from a Carbapenem Chiron Are Selective Inhibitors of Human Fatty Acid Amide Hydrolase versus Human Monoacylglycerol Lipase

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