Studies on semi-synthetic 7.ALPHA.-formamidocephalosporins. III. Synthesis and antibacterial activity of some 7.BETA.-(D-2-(aryl)-2-((4-ethyl-2,3-dioxopiperazin-1-yl)-carbonylamino)acetamido)-7.ALPHA.-formamido-ceph-3-em-4-carboxylate derivatives.

Cl, Branch; Mj, Basker; Sc, Finch; Aw, Guest; Fp, Harrington; Ac, Kaura; Sj, Knott; Ph, Milner; Mj, Pearson

doi:10.7164/antibiotics.40.646

Cited by 20 publications

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Cephalosporins

Roberts¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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CEPHALOSPORINSThe cephalosporins, a subgroup of β-lactam antibiotics, consist of a 4-membered lactam ring fused through the nitrogen and the adjacent tetrahedral carbon atom to a second heterocycle forming a 6-membered dihydrothiazine ring. Other structural features common to all the cephalosporins are a carboxyl group on the dihydrothiazine ring on the carbon next to the ring nitrogen and a functionalized amino group on C-7, the carbon of the β-lactam ring opposite the nitrogen. These features are evidenced in 7-aminocephalosporanic acid [957-68-6] (7-ACA), C 10 H 12 N 2 O 5 S 1. Cephalosporins, like all β-lactam antibiotics, exert their antibacterial effect by interfering with the synthesis of the bacterial cell wall. These antibiotics tend to be "irreversible" inhibitors of cell wall biosynthesis and they are usually bactericidal at concentrations close to their bacteriostatic levels. Cephalosporins are widely used for treating bacterial infections. They are highly effective antibiotics and have low toxicity.

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Cephalosporins

Roberts¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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β‐Lactam Antibiotics

Andreotti

Biondi

Modugno

2003

Burger's Medicinal Chemistry and Drug Discovery

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This chapter reviews the history of β‐lactams from the discovery of penicillin in 1928 to the more recently studied and the current trends in the field. The most relevant aspects related to the mechanism of action of β‐lactams are covered, and the various mechanisms of resistance to currently available β‐lactams that bacteria have adopted since the introduction of penicillin are described. A classification of β‐lactamases and their relevance in clinics is also provided. Applications of β‐lactams both in the hospital and in the community are reported, with particular attention to their pharmacokinetic properties, related side effects, and their therapeutic indications. The history and discovery of β‐lactams are described and all major classes are covered: penicillins, cephalosporins, oxacephems, carbacephems, penems, monobactams and nocardicins, carbapenems and trinems, classical (e.g., clavulanic acid, sulbactam, tazobactam), and the more recently disclosed β‐lactamase inhibitors. Several aspects related to the most recent developments in β‐lactams are also covered: new molecules active against difficult Gram‐positive strains or endowed with an antibacterial broad spectrum of action; potent orally active β‐lactams; injectable β‐lactams; and β‐lactamase inhibitors. The chapter concludes with a continuing analysis of the industry‐driven trends and the most recent new application of β‐lactams as inhibitors of protein export in bacteria. Finally, a few very interesting Web addresses and a comprehensive reference list are also provided.

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β‐Lactam Antibiotics

Testero

Fisher

Mobashery

2010

Burger's Medicinal Chemistry and Drug Discovery

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The β‐lactam classes of antibacterials are preeminent in the treatment of bacterial infection due to their unparalleled clinical efficacy and clinical safety. Following the discovery of the penicillins, successive β‐lactam drug discovery has added the cephalosporin, penem cephamycin, clavulanate, monobactam, nocardicin, and carbapenem subclasses. The driving force behind much of this era of discovery is the staggering ability of pathogenic bacteria to adapt previous generations of the β‐lactam by the acquisition and expression of resistance mechanisms. Although many factors contribute to β‐lactam resistance, alterations to the molecular targets of the β‐lactams (the penicillin binding proteins) and the use of enzymes (the β‐lactamases) capable of the hydrolytic deactivation of the β‐lactams are paramount. This review traces the historical development of β‐lactam drug discovery, with emphasis on the most recent progress in the medicinal chemistry, biochemistry, and microbiology of the β‐lactams leading to the discovery of new generation β‐lactam antibacterials effective against the Gram‐negative and ‐positive bacterial pathogens of current medical concern.

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Studies on semi-synthetic 7.ALPHA.-formamidocephalosporins. III. Synthesis and antibacterial activity of some 7.BETA.-(D-2-(aryl)-2-((4-ethyl-2,3-dioxopiperazin-1-yl)-carbonylamino)acetamido)-7.ALPHA.-formamido-ceph-3-em-4-carboxylate derivatives.

Cited by 20 publications

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Cephalosporins

Cephalosporins

β‐Lactam Antibiotics

β‐Lactam Antibiotics

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