Monocyclic antibiotic .beta.-lactams

Abdulla, Riaz F.; Fuhr, Kenneth H.

doi:10.1021/jm00240a022

Cited by 32 publications

(14 citation statements)

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“…In the past there was relatively little interest in monocyclic P-lactam antibacterial agents because the biological activity of some of these compounds [4] appeared only modest compared to penicillins and cephalosporins [5]. However, the discovery of the excellent in uiuo activity of nocardicin [6] …”

Section: IImentioning

confidence: 99%

MINDO/3 Study of N-Substituted Monocyclic β-Lactam Structures

Boyd

2009

Int. J. Quantum Chem.

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Molecular orbital computer experiments are used to determine the conformational preferences of N-R-3-aminoazetidin-2-ones. where R is methyl or vinyl. These structures, which model both monocyclic and bicyclic antibacterial agents, are found to be most stable when the R substituent is coplanar with the four-membered ring. Only 1-2 kcal/mole and 5-7 kcal/mole are required to twist the model structures into conformations with the CC-NCR dihedral angle around the &lactam C-N bond equal to that in A3-cephalosporins and penicillins, respectively. Twisting is shown to weaken the C-N bond and to make the carbonyl more susceptible to nucleophilic attack. Implications of the results to understanding structure-activity relationships of p-lactam antibiotics are discussed. The MIND0/3 method predicts the inversion barrier of NH3 satisfactorily at about 6 kcal/mole.

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Section: IImentioning

confidence: 99%

MINDO/3 Study of N-Substituted Monocyclic β-Lactam Structures

Boyd

2009

Int. J. Quantum Chem.

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“…The drugs with 2-azetidinone scaffold are penicillins, cephalosporins, carbapenems, nocardicins, monobactams, clavulanic acid, sulbactams and tazobactams. These drugs had been used widely as chemotherapeutic agents to treat various microbial diseases [9][10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents

Kayarmar

Nagaraja

Naik

et al. 2017

Journal of Saudi Chemical Society

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A new series of N-substituted azetidinones (9a-h) synthesized by condensation of 4-arylidene hydrazino 1-isobutyl-1H-imidazo[4,5-c]quinolines (8a-h) with chloroacetyl chloride afforded 4-arylazetidin-2-ones (9a-h). The synthesized compounds were characterized by 1 H NMR, 13 C NMR, mass spectral and elemental analyses. All synthesized compounds were screened for their in vitro antimicrobial and anticancer activities. The hydrazone derivatives (8a-h) showed good antibacterial activity. Compounds 9a and 9b exhibited good anticancer activity. In a molecular docking study compounds 9a and 9b showed minimum binding energy and good affinity towards the active pocket. Thus, are believed to be good inhibitors of b-tubulin.

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“…An emerging strategy within drug discovery programs comprises pharmacophore hybridization, in which two bioactive moieties are covalently linked and available as a single hybrid entity. Among pharmacologically important heterocyclic compounds, the β‐lactams are one of the key units in the most widely used class of antibacterial agents due to their interesting biological properties , which have stimulated exceptional interest in biochemistry and pharmacology . Many other biological activities have been associated with β‐lactam‐containing structures as well, such as inhibition of HIV‐1 protease , cholesterol absorption inhibition , antitumor activity , and antimalarial activity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structure of Novel β‐Lactam Derivatives Bearing Quinoline Moiety via [2 + 2] Cycloaddition

Lin

Peng

Fei

et al. 2015

Journal of Heterocyclic Chem

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A series of new β‐lactam derivatives 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l were synthesized from [2 + 2] cycloaddition reaction of imines containing quinoline moiety 3a, 3b, 3c, 3d, 3e, 3f with ketene generated in situ from chloroacetyl chloride in dry Et3N. The structures of the prepared compounds were characterized by IR, MS, 1H NMR, and elemental analysis. In addition, the structure of (4i) was determined by single crystal X‐ray crystallography.

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Monocyclic antibiotic .beta.-lactams

Cited by 32 publications

References 0 publications

MINDO/3 Study of N-Substituted Monocyclic β-Lactam Structures

MINDO/3 Study of N-Substituted Monocyclic β-Lactam Structures

Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents

Synthesis and Crystal Structure of Novel β‐Lactam Derivatives Bearing Quinoline Moiety via [2 + 2] Cycloaddition

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