Reformatsky reactions with N-arylpyrrolidine-2-thiones: synthesis of tricyclic analogues of quinolone antibacterial agents
TL;DR: In this article, a zinc-mediated reformatsky reaction between diethyl bromomalonate and N -arylpyrrolidine-2-thiones was used to synthesize quinolone antibiotics.
About: This article is published in Tetrahedron.The article was published on 2001-11-19. It has received 82 citations till now. The article focuses on the topics: Reformatsky reaction.
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196 citations
TL;DR: Enaminoketones and enaminonitriles have proven to be versatile building blocks for the synthesis of various heterocycles such as pyridine, pyrimidine and pyrrole derivatives.
165 citations
TL;DR: The enriched SAR paves the way to the further rational development of 4-quinolones with a unique mechanism of action different from that of the currently used drugs to overcome the resistance, well-tolerated and low toxic profiles.
130 citations
TL;DR: A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide.
Abstract: A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.
126 citations
TL;DR: In this article, the performance of different supported heteropoly acids (HPAs) in the synthesis of β-enaminones and βenamino esters from various substituted amines and β-diketones or β-keto esters has been studied.
70 citations
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TL;DR: Improved bioavailability is one target achieved with most of the more recent compounds allowing for once-daily dosing, and improvements in pharmacokinetic properties, greater activity against gram-positive cocci and anaerobes, activity against fluoroquinolone-resistant strains, and improved in activity against non-fermentative gram-negative species.
540 citations
TL;DR: In this article, it was shown that sulfide contraction via alkylative coupling (see scheme p. 729) is a potentially general method for the synthesis of secondary vinylogous amides and enolizable β-dicarbonyl compounds.
Abstract: The experiments described in reaction schemes 1–12 indicate that sulfide contraction via alkylative coupling (see scheme p. 729) is a potentially general method for the synthesis of secondary vinylogous amides and enolizable β-dicarbonyl compounds.
256 citations
254 citations
TL;DR: This review will discuss the mechanistic basis for drug efficacy and interactions between these compounds and their topoisomerase targets, as well as cultured mammalian cells and in vivo tumor models.
Abstract: Quinolones are a very important family of antibacterial agents that are widely prescribed for the treatment of infections in humans. Although the founding members of this drug class had little clinical impact, successive generations include the most active and broad spectrum oral antibacterials currently in use. In contrast to most other anti-infective drugs, quinolones do not kill bacteria by inhibiting a critical cellular process. Rather, they corrupt the activities of two essential enzymes, DNA gyrase and topoisomerase IV, and induce them to kill cells by generating high levels of double-stranded DNA breaks. A second unique aspect of quinolones is their differential ability to target these two enzymes in different bacteria. Depending upon the bacterial species and quinolone employed, either DNA gyrase or topoisomerase IV serves as the primary cytotoxic target of drug action. While this unusual feature initially stymied development of quinolones with high activity against Gram-positive bacteria, it ultimately opened new vistas for the clinical use of this drug class. In addition to the antibacterial quinolones, specific members of this drug family display high activity against eukaryotic type II topoisomerases, as well as cultured mammalian cells and in vivo tumor models. These antineoplastic quinolones represent a potentially important source of new anticancer agents and provide an opportunity to examine drug mechanism across divergent species. Because of the clinical importance of quinolones, this review will discuss the mechanistic basis for drug efficacy and interactions between these compounds and their topoisomerase targets.
174 citations
157 citations