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Cinchona combinations

The success of quinine inspired the search for other antimalarials. The greatest impetus for the development of synthetic dmgs came this century when the two World Wars intermpted the supply of cinchona bark to the combatants. A stmcturally related 4-quinolinemethanol is mefloquine (65, Lariam [51773-92-3]) which now serves as an effective alternative agent for chloroquine-resistant P. falciparum. This is a potent substance that requires less than one-tenth the dose of quinine to effect cures. There are some untoward side effects associated with this dmg such as gastrointestinal upset and dizziness, but they tend to be transient. Mefloquine is not recommended for use by those using beta-blockers, those whose job requires fine coordination and spatial discrimination, or those with a history of epilepsy or psychiatric disorders. A combination of mefloquine with Fansidar (a mixture of pyrimethamine and sulfadoxine) is known as Fansimef but its use is not recommended. Resistance to mefloquine has been reported even though the compound has not been in wide use. [Pg.273]

Numerous new salts and additive compounds of cinchona alkaloids, and especially of quinine, have been described, of which only a few can be mentioned as examples quinine additive compounds with sulph-anilamide, t quinine salts of (+) and (—)-pantothenic acid, °( > quinine sulphamate and disulphamate, °( organo-mercury compounds of quinine and cinchonine such as quinine-monomercuric chloride. Various salts and combinations of quinine have also been protected by patent, e.g., ascorbates and nicotinates. [Pg.423]

The cinchona alkaloids on degradation break down into derivatives of (1) quinoline and (2) quinuclidine and the synthesis of any one of them involves the preparation of each of these two halves in a form suitable for combination. [Pg.454]

The most successful modifier is cinchonidine and its enantiomer cinchonine, but some work in expanding the repertoire of substrate/modifier/catalyst combinations has been reported (S)-(-)-l-(l-naphthyl)ethylamine or (//)-1 -(I -naphth T)eth Tamine for Pt/alumina [108,231], derivatives of cinchona alkaloid such as 10,11-dihydrocinchonidine [36,71], 2-phenyl-9-deoxy-10, 11-dihydrocinchonidine [55], and O-methyl-cinchonidine for Pt/alumina [133], ephedrine for Pd/alumina [107], (-)-dihydroapovincaminic acid ethyl ester (-)-DHVIN for Pd/TiOz [122], (-)-dihydrovinpocetine for Pt/alumina [42], chiral amines such as 1 -(1 -naphtln I)-2-(I -pyrro 1 idiny 1) ethanol, l-(9-anthracenyl)-2-(l-pyrrolidinyl)ethanol, l-(9-triptycenyl)-2-(l-pyrrol idi nyl)cthanol, (Z )-2-(l-pyrrolidinyl)-l-(l-naphthyl)ethanol for Pt/alumina [37,116], D- and L-histidine and methyl esters of d- and L-tryptophan for Pt/alumina [35], morphine alkaloids [113],... [Pg.511]

The best studied systems are the Raney Ni/tartaric acid/NaBr combination, for the hydrogenation of / -functionalized ketones, and the Pt- and Pd-on-support/cinchona alkaloid systems for the enantioselective hydrogenation of a-functionalized ketones. [Pg.114]

The catalyst is a combination of a chemo-catalyst and a natural product taken from the cinchona alkaloids giving amazing results. In phosphine catalysed asymmetric catalysis these types of structures are lacking, as nature does not produce phosphines ( ) and the phosphines used in the early years of development of asymmetric homogeneous catalysis lacked the complexity of... [Pg.309]

All the material world is formed of mixtures, aggregates or more complex combinations of pure substances. For example, it is well known that the bark of the Cinchona tree Cinchona calisaya) shows a remarkable antimalarial activity, which is due, not to the bark as such, but to some "pure substance" which forms an integral part of it. In 1820, the French pharmacists Pelletier and Caventou isolated the active principle of the Cinchona bark, which they called quinine, as a pure, crystalline substance, m.p. 177 °C (dec), -169°, and assigned an elemental... [Pg.6]

Uozumi has explored a series of (25, 4/ )-4-hydroxyproline-derived 2-aryl-6-hydroxy-hexahydro-lFf-pyrrolo[l,2-c]imidazolones as potential alternatives to cinchona alkaloid-based catalysts for the alcoholative ASD of meio-anhydrides (Fig. 16) [226]. Uozumi screened a small library of catalysts prepared by a four-step, two-pot reaction sequence from 4-hydroxyproline in combination with an aldehyde and an aniline. The most selective member, compound 67, mediated the methanolytic ASD of cw-hexahydrophthalic anhydride in 89% ee when employed at the 10 mol% level for 20 h at -25 °C in toluene [226]. [Pg.272]

Other Cinchona Alkaloids Dissolve about 2.5 g of sample in 60 mL of water contained in a separator, add 10 mL of 6 A ammonium hydroxide, extract the mixture successively with 30 mL and 20 mL of chloroform, and evaporate the combined chloroform extracts to dryness on a steam bath. Dissolve 1.5 g of the residue in 25 mL of alcohol dilute the solution with 50 mL of hot water add 1 A sulfuric acid (about 5 mL) until the solution is acid, using 2 drops of methyl red TS as the indicator and neutralize the excess acid with 1 A sodium hydroxide. Evaporate the solution to dryness on a steam bath,... [Pg.380]

The cinchona tree, from the bark of which these alkaloids are obtained, was originally found only on the eastern slope of the Andes in South America. The cultivation of this species, and other species of the same genus, was introduced into Java, India, Ceylon, Jamaica and Australia. At present the production of bark in Java is greater than in any other country. As early as 1639 the cinchona bark was introduced into Europe but it was not until 1792 that an impure alkaloid was isolated and a little later given the name quina. In 1820 this impure alkaloid was separated into two compounds named quinine and cinchonine. The bark contains about 3 per cent quinine combined with acids, tannic and quinic, from which it is set free by the action of lime. The free base is then extracted with petroleum ether or... [Pg.888]

The Sharpless asymmetric epoxidation of allyl alcohol gives the glycidol derivative 61 in 90% ee after in situ tosylation of 60 [63]. This process is working on a multiton-a-year scale (Arco Co., USA), facilitating the synthesis of a variety of /0-blockers. Asymmetric dihydroxylation of the allyl ether 63 catalyzed by a combined system of OSO4 and the cinchona alkaloid-based ligand 65 allows the commercial synthesis of the propranolol intermediate 64 in 91 % (Sepracor Co., USA) [64]. [Pg.571]

Alkylations. Highly enantioselective alkylation of t-butyl 4,4-bis (p-dimethyl-aminophenyl)-3-butenoate and t-butyl A -diphenylmethyleneglycine in the presence of a quatemized cinchona alkaloid results. The salt plays a dual role in asymmetric induction and as a phase-transfer catalyst. The products from the former reaction can be cleaved at the double bond to furnish chiral malonaldehydic esters which have many obvious synthetic applications. A combination of PTC, LiCl, and an organic base (e.g., DBU) favors the enantioselective alkylation of a chiral A-acylimidazolidinone in which the acyl side chain is derived from glycine. ... [Pg.302]


See other pages where Cinchona combinations is mentioned: [Pg.319]    [Pg.681]    [Pg.110]    [Pg.240]    [Pg.242]    [Pg.259]    [Pg.89]    [Pg.278]    [Pg.147]    [Pg.265]    [Pg.196]    [Pg.263]    [Pg.569]    [Pg.19]    [Pg.565]    [Pg.569]    [Pg.175]    [Pg.84]    [Pg.198]    [Pg.362]    [Pg.35]    [Pg.35]    [Pg.189]    [Pg.110]    [Pg.207]    [Pg.163]    [Pg.195]    [Pg.247]    [Pg.217]    [Pg.5446]    [Pg.235]    [Pg.59]    [Pg.131]    [Pg.135]    [Pg.136]    [Pg.291]    [Pg.1180]    [Pg.87]   
See also in sourсe #XX -- [ Pg.93 ]




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