Structure–Activity Relationships of Antitubercular Nitroimidazoles. 3. Exploration of the Linker and Lipophilic Tail of ((S)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-Amino PA-824).

Cherian, Joseph; Choi, Inhee; Nayyar, Amit; Manjunatha, Ujjini H.; Mukherjee, Tathagata; Lee, Yong Sok; Boshoff, Helena I.; Singh, Ramandeep; Ha, Young Hwan; Goodwin, Michael; Lakshminarayana, Suresh B.; Niyomrattanakit, Pornwaratt; Jiricek, Jan; Ravindran, Sindhu; Dick, Thomas; Keller, Thomas H.; Dartois, Véronique; Barry, Clifton E.

doi:10.1021/jm1010644

Cited by 38 publications

(41 citation statements)

References 23 publications

(50 reference statements)

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“…: 9 To a 250 mL round-bottom flask containing a Teflon-coated magnetic stir bar, were added (2-cyclopropoxyphenyl)methanol (S10) (899 mg, 5.44 mmol) and DCM (50 mL). PCC (2.35 g, 10.88 mmol) was added in a single portion.…”

Section: -Cyclopropoxybenzaldehyde (14)mentioning

confidence: 99%

Origins of Initiation Rate Differences in Ruthenium Olefin Metathesis Catalysts Containing Chelating Benzylidenes

et al. 2015

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A series of second-generation ruthenium olefin metathesis catalysts was investigated using a combination of reaction kinetics, X-ray crystallography, NMR spectroscopy, and DFT calculations in order to determine the relationship between the structure of the chelating oalkoxybenzylidene and the observed initiation rate. Included in this series were previously reported catalysts containing a variety of benzylidene modifications as well as four new catalysts containing cyclopropoxy, neopentyloxy, 1-adamantyloxy, and 2-adamantyloxy groups. The initiation rates of this series of catalysts were determined using a UV/vis assay. All four new catalysts were observed to be faster-initiating than the corresponding isopropoxy control, and the 2-adamantyloxy catalyst was found to be among the fastest-initiating Hoveyda-type catalysts reported to date. Analysis of the X-ray crystal structures and computed energy-minimized structures of these catalysts revealed no correlation between the Ru−O bond length and Ru−O bond strength. On the other hand, the initiation rate was found to correlate strongly with the computed Ru−O bond strength. This latter finding enables both the rationalization and prediction of catalyst initiation through the calculation of a single thermodynamic parameter in which no assumptions about the mechanism of the initiation step are made.

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Section: -Cyclopropoxybenzaldehyde (14)mentioning

confidence: 99%

Origins of Initiation Rate Differences in Ruthenium Olefin Metathesis Catalysts Containing Chelating Benzylidenes

et al. 2015

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“…When fluorine atoms or trifluoromethyl groups were introduced into either the peptidic chain or the C-terminal end of cationic pentapeptides, the antimicrobial activity always improved by diminishing the minimal inhibitory concentration (MIC) [17]. A recent report on the structure activity relationships of antitubercular nitroimidazoles highlighted the high activity achieved by the inclusion of trifluoromethoxybenzyl substituents in the nitroimidazoles [18]. Carbon films with a high fluorine content exhibited excellent antibacterial properties against E. coli growth [19].…”

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confidence: 99%

A Study of Fluorinated β-Nitrostyrenes as Antimicrobial Agents

Cornell

Nicoletti

et al. 2012

Applied Sciences

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Abstract:The effect of variously fluorine-substituted β-methyl-β-nitrostyrenes on their antimicrobial activity was investigated. Their efficacy was determined by minimum inhibition concentration (MIC) in cultures of Gram positive and Gram negative bacteria and a fungus. Highest activity against the Gram negative bacterium, E.coli, was achieved with 4-fluorine-aryl substituted β-methyl-β-nitrostyrenes, while most compounds gave excellent results against gram positive bacteria. Importantly, the addition of the β-methyl group profoundly enhanced the antibacterial activity of the compounds tested. The comparative K D values for the most potent compounds against E.coli were much lower than those required for the gram positive and fungus counterparts. This investigation illustrated that fluorine substituted nitropropenylarenes have enhanced antimicrobial activity suitable for antibiotic applications.

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“…44 Já no trabalho de Meng e colaboradores foram sintetizados os maleatos ou cloridratos de derivados de SQ-109, onde foi observado que a presença de um átomo de flúor ou de uma metoxila no carbono terciário da adamantila vizinha ao nitrogênio do grupo etilenodiamino aumenta a atividade, em especial com o átomo de flúor onde a potência é duplicada (54 e 55 Figura 12). Outras modificações no grupo geranila e adamantila não aumentaram a atividade (56)(57)(58)Figura 12). 45 O esquema 11 mostra um resumo da relação estrutura-atividade para compostos desta série.…”

Section: Figura 11 Resultados Da Avaliação In Vitro Da Sq-109 E Análunclassified

The Medicinal Chemistry of Novel Molecules in Clinical Trials for Tuberculosis Treatment

Branco¹,

Pinto²,

Boechat³

2012

Revista Virtual De Química

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Tuberculosis is a serious public health problem, especially in underdeveloped or developing countries. The first line anti-TB treatment was developed more than 40 years ago. In addition to the development of strains of Mycobacterium tuberculosis resistant to multiple drugs and co-infection with the AIDS virus, has worsened the situation of this disease worldwide. The urgent need for new therapeutic options active against multidrug-resistant strains and concurrently capable to be used with AIDS treatment has led industries, governments and nongovernmental organizations to develop new drugs. This review describes the process of developing new anti-TB drugs and the chemistry of new molecules drug candidates that are in clinical trials for this disease listed in the global portfolio of Stop TB Partnership.Keywords: Tuberculosis; clinical trial; medicinal chemistry; drug design. ResumoA tuberculose é um grave problema de saúde pública, especialmente em países subdesenvolvidos ou em desenvolvimento. O tratamento anti-TB de primeira escolha foi desenvolvido há mais de 40 anos. Isto, aliado ao desenvolvimento de cepas de Mycobacterium tuberculosis resistentes a múltiplos fármacos e a coinfecção com o vírus da AIDS, tem agravado o quadro desta doença em todo o mundo. A urgente necessidade de tratamentos mais efetivos contra cepas multirresistentes e que possam ser utilizados concomitantemente com medicamentos contra a AIDS, tem estimulado as indústrias, governos e organizações não governamentais a buscar novos fármacos. Esta revisão descreve o processo de desenvolvimento de novos fármacos anti-TB e a química medicinal de novas moléculas em fase clínica para esta patologia, listadas no portfólio global da Stop TB Partnership. Palavras-chave:Tuberculose; fase clínica; química medicinal; planejamento.

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Structure–Activity Relationships of Antitubercular Nitroimidazoles. 3. Exploration of the Linker and Lipophilic Tail of ((S)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-Amino PA-824).

Cited by 38 publications

References 23 publications

Origins of Initiation Rate Differences in Ruthenium Olefin Metathesis Catalysts Containing Chelating Benzylidenes

Origins of Initiation Rate Differences in Ruthenium Olefin Metathesis Catalysts Containing Chelating Benzylidenes

A Study of Fluorinated β-Nitrostyrenes as Antimicrobial Agents

The Medicinal Chemistry of Novel Molecules in Clinical Trials for Tuberculosis Treatment

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