Recent Advances in the Synthesis of Antibacterial Quinolones

Rádl, S.; Bouzard, D.

doi:10.3987/rev-92-446

Cited by 48 publications

(13 citation statements)

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“…[54] Solvent-Free Jacobs-Gould Reaction A key step in the synthesis of quinolone antibacterial agents is formation of a ring possessing an oxo group. [56,57] The vehicle is often a Jacobs-Gould reaction employing elevated temperatures over several hours. [58,59] An environmentally undesirable eutectic mixture of diphenyl ether and biphenyl usually doubles as a diluent and heat transfer medium.…”

Section: Kinetic Productsmentioning

confidence: 99%

A Strategic, 'Green' Approach to Organic Chemistry with Microwave Assistance and Predictive Yield Optimization as Core, Enabling Technologies

Strauss¹

2009

Aust. J. Chem.

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Since 1988, we have pursued enabling technologies and methods as tools for 'green' synthetic chemistry. The developed technologies comprise hardware including catalytic membranes and continuous and batch microwave reactors that have established global markets, as well as interactive, predictive software for optimization of yields and translation of conditions. New methods include 'green' reactions such as a catalytic symmetrical etherification, Pd-catalyzed coupling processes and a multi-component cascade for aniline derivatives. Reactions and workup were facilitated through solvent-free conditions, aqueous media at high temperature and dimethylammonium dimethylcarbamate (dimcarb) as a 'distillable' protic ionic liquid, as well as by non-extractive techniques for product isolation. The technologies and methods were designed for use alone or in various combinations as desired. Consolidation of individual operations or processes into unit steps was achieved through multi-tasking: media, reactants, catalysts, and conditions were selected to serve several purposes at various stages of a reaction. The tools were used to establish a technology platform comprising structurally diverse oligomers, macrocycles, and rod-like molecules supplementary to those available through phenolformaldehyde chemistry. Dienone precursors were assembled from versatile building blocks containing complementary 'male' or 'female' fittings that were connected through inherently 'green' Claisen-Schmidt-type reactions. Isoaromatization afforded Horning-crowns, macrocyclic phenolic derivatives that were hybrids of calixarenes and crown ethers. Preliminary studies of organic substrates in salt water, with and without CO 2 , called into question proposals for disposal of anthropogenic CO 2 by deep-sea dispersal.

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Section: Kinetic Productsmentioning

confidence: 99%

A Strategic, 'Green' Approach to Organic Chemistry with Microwave Assistance and Predictive Yield Optimization as Core, Enabling Technologies

Strauss¹

2009

Aust. J. Chem.

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“…Recently sitafloxacin has been under phase III trials in Japan with oral and injectable formulations and this new fluoroquinolone is expected to be launched in 2006 [48][49][50][51][52]. Basically, there are two principal strategies for the construction of the quinolin-4-one nucleus both proceeding via enaminones intermediates, the Bayer and the Gould-Jacobs route [53] (Scheme 1). Basically, there are two principal strategies for the construction of the quinolin-4-one nucleus both proceeding via enaminones intermediates, the Bayer and the Gould-Jacobs route [53] (Scheme 1).…”

Section: Dw-116mentioning

confidence: 99%

New Fluoroquinolones: A Class of Potent Antibiotics

Souza

2005

MRMC

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The discovery of antibiotics opened a new era in the treatment against several pathogenic microorganisms that can disable or kill humans. The appearance of the fluoroquinolones (based on nalidixic acid, 4-quinolone-3-carboxylates), in the early 1980's, gave a new impetus in the treatment of infectious diseases. Despite these favourable properties, the earlier fluoroquinolones had limited potency against some clinically important organisms, especially Gram-positive pathogens so that the development of resistance to these organisms has become a serious problem. Thus the development of new fluoroquinolones with a better pharmacokinetic profile, potency, broad spectrum of activity, solubility, prolonged serum half-life and oral and parenteral routes of administration has been a major focus on recent research. The increasing interest in this class led me to review the promising new fluoroquinolones in clinical trials.

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“…15 A primeira delas foi desenvolvida por químicos da Bayer AG, sendo o anel quinolônico formado pela ciclização de intermediários 3-aminoacrilatos-2-(2-halobenzoil) 16 (Esquema 1). A outra estratégia sintética é conhecida como ciclização de Gould-Jacobs 17 , que é baseada na ciclização térmica ou catalisada, em meio ácido, de malonatos anilinometilênicos (Esquema 1).…”

Section: Estratégia Geral Que Permite a Obtenção De Diferentes Fluorqunclassified

Fármacos no combate à tuberculose: passado, presente e futuro

Souza¹,

Vasconcelos²

2005

Quím. Nova

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Recebido em 23/6/04; aceito em 15/10/04; publicado na web em 17/2/05 DRUGS AGAINST TUBERCULOSE: PAST, PRESENT AND FUTURE. Approximately every minute, somewhere in the world four people die from tuberculosis (TB), an infection of Mycobacterium tuberculosis with about 3 million deaths per year. In spite of these problems, unfortunaly, it is about 40 years that a novel drug was last introduced on the market. Due to the rapid spread of multi-drug resistant TB strains, resistant against all major anti-tuberculosis drugs, and the recent resurgence of the incidence of tuberculosis in association with the human immunodeficiency virus (HIV) infection and AIDS, we need urgently the development of new drugs to fight tuberculosis. This is covered in the present article.Keywords: tuberculosis, drugs, antibacterial. INTRODUÇÃOA tuberculose (TB) é uma doença contagiosa grave, com relatos de médicos na Grécia e na Roma antiga e, atualmente, acreditase que esta doença já era conhecida também no antigo Egito, já que pesquisadores encontraram lesões de tuberculose em múmias No decorrer do século XIX e até meados do século XX, era uma doença comum entre artistas e intelectuais, sendo relacionada a um estilo de vida boêmio considerada, uma "doença romântica" 1 . A TB é transmitida basicamente pelo ar e pode atingir todos os órgãos do corpo, porém como o BK se reproduz e se desenvolve rapidamente em áreas do corpo com muito oxigênio, o pulmão é o principal órgão atingido pela doença 2 . O espirro ou tosse de uma pessoa infectada joga no ar cerca de dois milhões de bacilos que permanecem em suspensão durante horas. Os sintomas da tuberculose, geralmente, são tosse crônica, febre, suor noturno, dor no tórax, anorexia (perda de apetite) e adinamia (falta de disposição) 3,4 . Os exames usados na tentativa do diagnóstico de certeza são a baciloscopia do escarro, a radiologia do tórax, o teste tuberculínico (PPD), que evidencia o contato prévio com o bacilo e a cultura do escarro ou outros líquidos em meio apropriado 1 . A tuberculose continua sendo um grave problema de saúde pública, especialmente em países em desenvolvimento, voltando a ocupar papel de destaque entre as principais doenças infectocontagiosas. Muitos foram os fatores que contribuíram para isso, podendo-se destacar a desigualdade social, os aglomerados populacionais, os movimentos migratórios, o envelhecimento da população, o aparecimento cada vez mais comum de cepas de bacilos resistentes aos fármacos conhecidos e o surgimento, na década de 80, da "Síndrome de Imunodeficiência Adquirida (SIDA)" ou "Acquired Immuno Deficiency Syndrome (AIDS)". DADOS ESTATÍSTICOSAtualmente a tuberculose mata no mundo aproximadamente 3,0 milhões de pessoas por ano, incluindo mais adultos que a AIDS, a malária e as doenças tropicais combinadas. Estima-se que cerca de 1,7 bilhões de indivíduos em todo o mundo estejam infectados pelo M. tuberculosis, o que corresponde a 30% da população mundial 5 , sendo que em países pobres, a estimativa é que 70% da população esteja infectada pelo bacilo de Ko...

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Recent Advances in the Synthesis of Antibacterial Quinolones

Cited by 48 publications

References 0 publications

A Strategic, 'Green' Approach to Organic Chemistry with Microwave Assistance and Predictive Yield Optimization as Core, Enabling Technologies

A Strategic, 'Green' Approach to Organic Chemistry with Microwave Assistance and Predictive Yield Optimization as Core, Enabling Technologies

New Fluoroquinolones: A Class of Potent Antibiotics

Fármacos no combate à tuberculose: passado, presente e futuro

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