A New and Simple Synthesis of Some 4-Substituted Imidazoles

Kasina, S.; Nematollahi, Jay

doi:10.1055/s-1975-23690

Cited by 16 publications

(5 citation statements)

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“…Ortho-selective SnAr displacement of 81 using ammonia provided 82 , which was then cross-coupled with 2-pyridylzinc chloride under Negishi conditions to give 83 . Sequential introduction of the C5 imidazolylamide under anionic SnAr conditions using 87 (Scheme ) followed by acid catalyzed cleavage of the tert -butyl group yielded 85 . Final conversion to the BI-urea 20 was then achieved via the two-step sequence of reduction and treatment of the resulting phenylenediamine with reagent B .…”

Section: Methodsmentioning

confidence: 99%

Novel Dual-Targeting Benzimidazole Urea Inhibitors of DNA Gyrase and Topoisomerase IV Possessing Potent Antibacterial Activity: Intelligent Design and Evolution through the Judicious Use of Structure-Guided Design and Stucture−Activity Relationships

et al. 2008

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The discovery of new antibacterial agents with novel mechanisms of action is necessary to overcome the problem of bacterial resistance that affects all currently used classes of antibiotics. Bacterial DNA gyrase and topoisomerase IV are well-characterized clinically validated targets of the fluoroquinolone antibiotics which exert their antibacterial activity through inhibition of the catalytic subunits. Inhibition of these targets through interaction with their ATP sites has been less clinically successful. The discovery and characterization of a new class of low molecular weight, synthetic inhibitors of gyrase and topoisomerase IV that bind to the ATP sites are presented. The benzimidazole ureas are dual targeting inhibitors of both enzymes and possess potent antibacterial activity against a wide spectrum of relevant pathogens responsible for hospital- and community-acquired infections. The discovery and optimization of this novel class of antibacterials by the use of structure-guided design, modeling, and structure-activity relationships are described. Data are presented for enzyme inhibition, antibacterial activity, and in vivo efficacy by oral and intravenous administration in two rodent infection models.

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Section: Methodsmentioning

confidence: 99%

Novel Dual-Targeting Benzimidazole Urea Inhibitors of DNA Gyrase and Topoisomerase IV Possessing Potent Antibacterial Activity: Intelligent Design and Evolution through the Judicious Use of Structure-Guided Design and Stucture−Activity Relationships

et al. 2008

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“…The latter was synthesized according to the procedure described by Kasina & Nematollahi (1975). The latter was synthesized according to the procedure described by Kasina & Nematollahi (1975).…”

Section: Methodsmentioning

confidence: 99%

“…Compound (II) was obtained as a secondary product during the synthesis of compound (I). The latter was synthesized according to the procedure described by Kasina & Nematollahi (1975). During the evaporation of the excess of the acetic anhydride used in the synthesis of (I), an enlargement device was inserted between the solution flask and the vacuum pump.…”

Section: Methodsmentioning

confidence: 99%

1-(1H-Imidazol-1-yl)ethanone

Merchán¹,

Stœckli-Evans²

2007

Acta Cryst E

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“…As noted by Kasina & Nematollahi (1975), alkyl 4imidazolecarboxylates and their derivatives are tedious to synthesize. They reported a simple synthesis based on the reaction of diimidazo[1,5-a;1 0 ,5 0 -d]pyrazine-5,10-dione, (I), with a number of reagents such as methanol, hydrazine, methylhydrazine and 1,1-dimethylhydrazine.…”

Section: Commentmentioning

confidence: 99%

“…2. Compound (I) was synthesized according to the procedure described by Kasina & Nematollahi (1975). Imidazole-4,5-dicarboxylic acid (2.0 g, 12.82 mmol) was introduced, under an atmosphere of nitrogen, into a 50 ml three-necked flask equipped with a magetic stirring bar.…”

Section: Commentmentioning

confidence: 99%