Über die Darstellung des 3‐[β‐Oxy‐äthyl]‐pyridins

Dornow, Alfred; Schacht, Wilhelm

doi:10.1002/cber.19470800606

Cited by 17 publications

(2 citation statements)

References 7 publications

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“…Por exemplo, a oxidação da 8-hidroxiquinolina 13 pelo ácido nítrico a 0 o C, durante 1 h, permite a formação do ácido quinolínico 6 com um rendimento quantitativo 16,17 …”

Section: Métodos De Preparação Do áCido Quinolínicounclassified

Métodos de preparação e atividade biológica do ácido quinolínico e derivados

Souza¹,

Almeida²,

Hyaric³

et al. 2003

Quím. Nova

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. In 1981 2,3-pyridine dicarboxylic acid (quinolinic acid) was discovery to be a selective agonist for the N-methyl -D-aspartic acid (NMDA) receptor. As a consequence it possesses neurotoxic activity resulting from overstimulation of the receptor. Quinolinic acid is implicated as an etiological factor in a range of neurodegenerative disease including AIDS related dementia, Huntington´s disease and Lyme disease. In the design of novel therapies to treat these diseases, some molecules have been identified as an important target. In this paper we described different methods to prepare quinolinic acid and derivatives.Keywords: quinolinic acid; NMDA receptor; AIDS related dementia. INTRODUÇÃOMais de um terço dos pacientes infectados pelo HIV sofrem de problemas neurológicos. Os sintomas incluem deficiência cognitiva e motora, conhecido como "AIDS dementia complex", mielopatia, neuropatia periférica e disfunções visuais 1 . A proporção de pacientes que sofrem de tais sintomas tende a aumentar à medida que as infecções oportunistas progridem. Segundo a maioria dos especialistas, uma vacina preventiva anti-HIV ou ainda um medicamento ideal é um objetivo a longo prazo e, todavia, incerto, sendo portanto necessário encontrar meios de curar os graves efeitos cognitivos associados à infecção causada pelo HIV. Este artigo aborda um suposto mecanismo da neurotoxicidade ligada ao HIV, assim como méto-dos de preparação do ácido quinolínico e de alguns de seus derivados, visando a prevenção ou a diminuição dos problemas cognitivos e motores provocados pelo HIV. Mecanismo da neurotoxidade associada à infecção pelo HIVOs problemas neurológicos associados ao HIV aparecem mesmo na ausência de infecções oportunistas e não são conseqüências de uma infecção direta dos neurônios pelo HIV 2 . Como se pode constatar a destruição ou danos dos neurônios no decorrer da doença, conclui-se que existe a liberação de um ou mais agente(s) neurotóxico(s) pelas células infectadas. Supõe-se que um destes agentes neurotóxicos seja o ácido quinolínico 6 (Esquema 1). Este composto endogênico, produto da degradação enzimática do triptofano 1, é de concentração particularmente elevada no líquido céfalo-raquidiano de pacientes portadores da AIDS 3 . Além desta evidência, o aumento da taxa de ácido quinolínico resulta em um forte aumento da taxa de cálcio nos neurônios, devido à sua interação direta ou indireta com o receptor ácido-N-metil-Daspártico (NMDA) 4-6 , uma das sub-classes dos receptores do glutamato no cérebro. Receptores do glutamatoO ácido L-glutâmico 7 é o principal neurotransmissor do sistema nervoso central dos mamíferos Entre estes três receptores ionotrópicos do glutamato, o receptor NMDA 8 é o mais estudado. Os receptores do glutamato estão implicados em processos fisiológicos fundamentais, tais como os fenô-menos de plasticidade sináptica e de memória 9 . É também conhecido que os aminoácidos excitadores podem causar efeitos neurotóxicos; estas moléculas provocam uma degenerescência neuronal em razão de uma liberação excessiva de cálcio...

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“…Por exemplo, a oxidação da 8-hidroxiquinolina 13 pelo ácido nítrico a 0 o C, durante 1 h, permite a formação do ácido quinolínico 6 com um rendimento quantitativo 16,17 …”

Section: Métodos De Preparação Do áCido Quinolínicounclassified

Métodos de preparação e atividade biológica do ácido quinolínico e derivados

Souza¹,

Almeida²,

Hyaric³

et al. 2003

Quím. Nova

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“…151-1520 C/10 mm, N 21 1.5390, yield 74% (13.5 g). Dornow & Schacht (1947) 2-(4-Pyridyl)ethyldialkylamines were prepared by the addition of the appropriate secondary amine to 4-vinylpyridine as described by Magnus & Levine (1956). The dihydrobromide was prepared from the base as described above.…”

Section: -(3-pyridyl)ethanolmentioning

confidence: 99%

Effects of Some Isomers and Analogues of Nicotine on Junctional Transmission

Barlow¹,

Hamilton²

1962

British Journal of Pharmacology and Chemotherapy

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A number of isomers and homologues of nicotine, (2-, 3-and 4-pyridylmethyl)-and [2-(2-, 3-and 4-pyridyl)ethyl]-dialkylamines and trialkylammonium salts, have been prepared. They have been tested for their ability to act like acetylcholine in causing contracture of the chick biventer-cervicis and, some of them, for their ability to stimulate the superior cervical ganglion of the cat, causing contracture of the nictitating membrane. All the compounds have been tested for their ability to block transmission on the superior cervical ganglion of the cat and on the rat diaphragm preparation, and most of them for ability to inhibit the enzymatic hydrolysis of acetylcholine, using an acetone-powder of dog caudate nucleus as a source of acetylcholinesterase. The dissociation constants of the compounds have been measured by electrometric titration. The dissociation constants were used to compute the amount of monovalent ion present in the conditions of the biological tests, and the activities of the compounds have, accordingly, been compared on an ionic, as well as on a molecular, basis. The two sets of figures do not differ greatly. Trimethyl[2-(3-pyridyl)ethyl]ammonium (23) was the most potent compound on the chick and cat preparations. On an ionic basis (that is, compared with the monovalent nicotinium ion) this was 2.6 times as active as nicotine on the chick biventer and 11 times as active on the cat superior cervical ganglion. On the rat diaphragm it was 7.1 times as active as nicotine and less active than 1-methyl-1-(3-pyridylmethyl)-pyrrolidinium (26) (9.5 times the nicotinium ion) and trimethyl(4-pyridylmethyl)-ammonium (21) (11 times). The relationships between structure and dissociation constant, anticholinesterase activity, and activity in the pharmacological tests have been discussed. Dale (1934) used the term " nicotine-like " to describe the actions of acetylcholine at ganglia and at the neuromuscular junction. Hey (1949Hey ( , 1952, reviewing the relationships between the chemical structure of esters and ethers of choline and their ability to stimulate ganglia, suggested that activity depended on the presence in a molecule of two features, the onium group and a suitably placed partial positive charge. In Hey's examples this charge was thought to be located on the ether oxygen atom separated by two carbon atoms from the quaternary nitrogen atom. Hey obtained support for this hypothesis from a study of the effects of a number of substituted phenyl ethers of choline on the blood pressure of cats, anaesthetized with chloralose and treated with atropine. Electron-withdrawing substituents on the benzene ring, which would increase the partial positive charge on the ether *Present address:

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The Synthesis of Aldehydes from Carboxylic Acids

Mosettig

2011

Organic Reactions

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The Rosenmund reduction of acid chlorides to the corresponding aldehydes was discussed in volume 4 of this series. There are a number of other less direct methods by which carboxylic acids can be converted into aldehydes and the purpose of this chapter is to consider the more useful of these procedures. Three of these methods, the hydrolytic decomposition of Reissert's compounds, the method of Grundmann, and the reductive desulfurization of thiol esters require acid chlorides as intermediates and in the respect are competitive with the Rosenmund reduction of acid chlorides. In the fourth method method, the McFadyen and Stevens synthesis, acid chlorides may be used for the preparation of the intermediate acyl hydrazides. Two additional methods, (Sonn and Muller, and Stephen) are based on the intermediate imido chlorides. These methods listed appear to be the one ones developed to the point where further discussion is profitable.

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Über die Darstellung des 3‐[β‐Oxy‐äthyl]‐pyridins

Cited by 17 publications

References 7 publications

Métodos de preparação e atividade biológica do ácido quinolínico e derivados

Métodos de preparação e atividade biológica do ácido quinolínico e derivados

Effects of Some Isomers and Analogues of Nicotine on Junctional Transmission

The Synthesis of Aldehydes from Carboxylic Acids

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