Hydrocuprein‐aminoalkyl‐äther

Slotta, K. H.; Behnisch, R.

doi:10.1002/cber.19350680503

Cited by 15 publications

(11 citation statements)

References 4 publications

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“…CCDC 1496937 [for 6a(SbF 6 )] contains the supplementary crystallographic data for this paper. 3053,3014,2949,1454,1209,922,806,760,656,484,459,413 General Procedure for Preparation of Piperidinium Salts N,N-Diethylpiperidinium Chloride [6 b(Cl)]: [35] At est tube was charged with sodium tetrafluoroborate (16.9 mg, 0.154 mmol) and dried under vacuum for 30 min. To the test tube were added anhydrous CH 3 CN (1.3 mL), 2-chloro-4,6-dimethoxy-1,3,5-triazine (27.3 mg, 0.155 mmol), and N,N-diethyl-N',N'-dimethyl-1,5-pentanediamine (2b,2 4.2 mg, 0.130 mmol) at room temperature.…”

Section: Preparation Of Diamides 14mentioning

confidence: 99%

Alcohol‐ and Amine‐Tolerant Synthesis of Six‐Membered Cyclic Quaternary Ammonium Salts by Using a Triazine‐Based Reagent

et al. 2016

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Six-membered cyclic quaternary ammonium salts, which are widely used in materials for both science and industry,w ere synthesized by using the triazine-based reagent 2-chloro-4,6-dimethoxy-1,3,5-triazine. The combination of sodium tetrafluoroborate as an additive and acetonitrile as as olvent was shown to be effective in the prevention of side reactions. Significantly,t his method is tolerant toward hydroxy and amino groups, whicha re labile under conventional reactionc onditions for the synthesiso fc yclic quaternary ammonium salts. Moreover,asterically hindered piperidinium salt was successfully prepared.Scheme2.Synthesis of vecuronium bromide containingbothamonoammonium salt andana mino groupb yp recipitation to prevent over-alkylation.[a] Dr.

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Section: Preparation Of Diamides 14mentioning

confidence: 99%

Alcohol‐ and Amine‐Tolerant Synthesis of Six‐Membered Cyclic Quaternary Ammonium Salts by Using a Triazine‐Based Reagent

et al. 2016

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“…Slotta & Behnisch (1935) found that the combination of dialkylarninoalkyl groups, of the type occurring in synthetic antimalarial compounds of known activity, with hydrocupreine resulted in a decrease in antimalarial activity.…”

Section: Atebrin and Related Compoundsmentioning

confidence: 98%

“…An increase in the molecular weight of the 2-alkoxy group led to a loss of activity due to increased toxicity, and the substitution of a methyl group for the 2-methoxy group had the same result. Slotta & Behnisch (1935) found that the combination of dialkylarninoalkyl groups, of the type occurring in synthetic antimalarial compounds of known activity, with hydrocupreine resulted in a decrease in antimalarial activity.…”

Section: Atebrin and Related Compoundsmentioning

confidence: 99%

Chemotherapy and avian malaria

Bishop

1942

Parasitology

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Malaria is endemic over a wide area of the earth's surface. Although popularly associated with tropical or subtropical countries, it occurs as far north as the south of Sweden and Lake Ladoga in Russia and as far south as Bechuanaland, Swaziland and Natal in South Africa and the Argentine in South America. Though most frequent in low-lying districts it may be found at altitudes as great as 6000–9000 ft.

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“…Among the general factors which have been variously emphasized in considering the mode of action of cinchonas are molecular weight (61,106,114), greater effectiveness at a somewhat alkaline pH (62, 78), and surface tension, which is lower in neutral or alkaline solution (17,78). Ostromislensky (93) stressed the importance of the colloidal nature of a medicinal and thought that the quinoline residue gives colloidal properties and bacterial specificity.…”

Section: )mentioning

confidence: 99%

Structure and Antipneumococcic Activity in the Cinchona Series.

Renfrew¹,

Cretcher²

1942

Chem. Rev.

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The present survey gives particular emphasis to recent studies of the antipneumococcic action of some cinchona derivatives. A brief historical survey is presented and reference is made to speculations concerning the mode of action of cinchonas in the animal body. Antipneumococcic action is analyzed with regard to isomeric and structural modifications of the cinchona molecule. A summary of recent data on bacteriostasis, toxicity, animal protection, pharmacologic testing, and clinical studies is given. Synthetic analogs are discussed in relation to significant structural factors.Cinchona alkaloids have been used as antimalarials since 1630, but evidence of the specific antipneumococcic action of these compounds dates only from 1911. RIorgenroth's (84) study of cinchonas as antipneumococcic agents has been described as "the first striking instance of the successful application of a chemical to the treatment of a bacterial infection in a laboratory animal" (53). Because Morgenroth had been studying quinine in relation to trypanosome infections in animals and was acquainted with the capsule-formation characteristic of trypanosomes, spirilla, and the pneumococcus, he was led to investigate the action of the alkaloid in pneumococcic septicemia in mice. There followed an extensive study of hydrocupreine ethers with the synthesis of the well-known optochin, vuein, and eucupin. Between 1919 and 1924 Heidelberger and Jacobs (42, 54) a t the Rockefeller Institute and Giemsa (32, 33) in Germany published the results of further studies in the hydrocupreine series. These results have been reviewed by von Oettingen (111) and by Houben (50), and the clinical findings have been discussed by Moore and Chesney (87), by Kolmer (63), and by Solis-Cohen (107).The remarkable antipneumococcic action of optochin has been a spur to reinvestigation of this field. In again studying cinchona derivatives the search was not so much for a compound of greater power but rather for a compound free from deleterious side-effects. The last decade has brought extensive synthesis in the field of apocinchonas. In the early 1930's methylapocupreinel [or 1 At the time the term apocupreine (8) was suggested, its use was based firstly on the similarities of apocupreine (formula 11) and cupreine (formula I), which differ chemically only in the 3-substituent of ethylidene or vinyl, respectively, and secondly on the established usage of Leger (59, 66) in applying the terms apocinchonine and apocinchonidine (characterized by the ethylidene side chain) to the corresponding substances derived from cinchonine and cinchonidine. In the case of quinine, demethylation is accomplished by boiling with 60 per cent sulfuric acid; a shift of the double bond also occurs. The product, called apoquinine by Hesse (49), consists of substances of different toxicities and antipneumococcic powers and these give derivatives of various biological properties. The name 49

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Hydrocuprein‐aminoalkyl‐äther

Cited by 15 publications

References 4 publications

Alcohol‐ and Amine‐Tolerant Synthesis of Six‐Membered Cyclic Quaternary Ammonium Salts by Using a Triazine‐Based Reagent

Alcohol‐ and Amine‐Tolerant Synthesis of Six‐Membered Cyclic Quaternary Ammonium Salts by Using a Triazine‐Based Reagent

Chemotherapy and avian malaria

Structure and Antipneumococcic Activity in the Cinchona Series.

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