Stucture and Chemotherapeutic Activities of Sulfanilamide Derivatives.

Northey, E. H.

doi:10.1021/cr60086a006

Cited by 37 publications

(8 citation statements)

References 30 publications

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“…The products were extracted by a solvent such as hot water, ethanol or THF. The yields of these reactions were higher (70-95%) and the reaction times were shorter (5-20 min) than conventional methods [6][7][8][9][10] (Table 1).…”

Section: Resultsmentioning

confidence: 92%

“…5 Different methods for the preparation of these compounds have been reported. [6][7][8][9][10] In some of these methods the yields of products are not high, 6,7 the solvent is toxic (pyridine), 6 the reaction times are longer, 6,9 and also the starting materials (sulfinic acid salt) are not commercially available. 10 Recently, considerable attention has been paid to solvent-free reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

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An Efficient Synthesis of Sulfonylhydrazides and Sulfonylsemicarbazides by Utilizing Alumina as a Catalyst

Safaei‐Ghomi

2007

J Chinese Chemical Soc

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Section: Resultsmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Sulfonylhydrazides and Sulfonylsemicarbazides by Utilizing Alumina as a Catalyst

Safaei‐Ghomi

2007

J Chinese Chemical Soc

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“…g. Sulfonamide structure. It is not within the scope of this review to consider in any great detail the tremendous mass of literature dealing with the effect of chemical structure on sulfonamide activity (212). The theoretical approaches to this problem supplied by Bell and Roblin and byKumler and Daniels have already been presented.…”

Section: The Biphasic Action Of Sulfonamidesmentioning

confidence: 99%

“…It was soon discovered that other bacterial infections are also susceptible to Prontosil. Today, with the thousands of derivatives which have been prepared, it is seen that any one drug, which possesses any activity at all, varies tremendously in effectiveness on different bacteria, although probably no organism is completely insensitive (84,212).…”

Section: Delay Vs No Delay In Sulfonamide Actionmentioning

confidence: 99%

The Mode of Action of the Sulfonamides

Henry

1944

JAMA

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“…Attempts to combine the sulfanilamide molecule and an aminoquinoline have not been productive (88,99) in the simple derivatives, but in the testing of N4-alkylaminoacetylsulfanilamidoquinolines Juneja (58) has cIaimed results "comparing favorably with sulfapyridine." Synthetic derivatives of 6-methoxyquinoline in which a pyrryl (60) or a piperidyl (1) nucleus or a 0-dialkylaminomethyl group (61) has been substituted for the quinuclidine portion of the cinchonas have shown action on paramecia or antimalarial power, but no study of the antipneumococcic action has been reported.…”

Section: A Simple Substituted Quinolinesmentioning

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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Stucture and Chemotherapeutic Activities of Sulfanilamide Derivatives.

Cited by 37 publications

References 30 publications

An Efficient Synthesis of Sulfonylhydrazides and Sulfonylsemicarbazides by Utilizing Alumina as a Catalyst

An Efficient Synthesis of Sulfonylhydrazides and Sulfonylsemicarbazides by Utilizing Alumina as a Catalyst

The Mode of Action of the Sulfonamides

Structure and Antipneumococcic Activity in the Cinchona Series.

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