Sulfanilyl Derivatives of Pyridine and Quinoline Amines

Winterbottom, Robert

doi:10.1021/ja01858a045

Cited by 12 publications

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“…The compound 6 preparation was divided into six portions for reaction with six different amines in the presence of pyridine to generate sulfonamides 7. The basic hydrolysis of these MeO-PEG sulfonamides completed the construction of an arylsulfonamide library consisting of six members (see Fig. 3 (19), or by heating the reaction mixture in pyridine solvent at 65°C for an hour (method C) (20). The MeO-PEG polymer was precipitated from the homogeneous solution by the addition of diethyl ether, washed with ethanol, and dried under vacuum to give the desired product quantitatively.…”

Section: Methodsmentioning

confidence: 99%

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Liquid-phase combinatorial synthesis.

Han

Wolfe

Brenner

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

169

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Section: Methodsmentioning

confidence: 99%

“…O-(MeO-PEG) N-[4-(alkylaminosulfonyl)phenyl]carbamate (0.45 g) was dissolved in 0.5 M NaOH (10 ml) and heated at 90°C for 30 min (19,20). The reaction mixture was cooled to 4°C and neutralized to pH 6-8 with concentrated HCI.…”

Section: Methodsmentioning

confidence: 99%

Liquid-phase combinatorial synthesis.

Han

Wolfe

Brenner

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

169

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“…(14, 29,190) CH,- (3) W-Heterocyclicsulfanilamides: two or more nitrogen atoms in the heterocyclic system (see table 14) 2-Sulfanilamidopyrimidine ("sulfadiazine") (159) has shown several important advantages over sulfapyridine in preliminary studies. It is very readily absorbed, so that adequate blood levels can be maintained at lower dosage levels.…”

Section: Tablementioning

confidence: 99%

“…-Svlfanilamidoquinolines Ra r/Vn• H,N< )>SOaN-Rt Ri ACTIV-ITY REFERENCES X X ± (42, 54, 132, 183) (190) X X X X + (14, 190) (14,132,190) …”

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confidence: 99%

Stucture and Chemotherapeutic Activities of Sulfanilamide Derivatives.

Northey¹

1940

Chem. Rev.

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“…As a result of the basestrengthening effect of an acidic solvent, strong bases such as diethylamine which couple satisfactorily in water are completely ionized in acetic acid and thus fail to react. 3 The general behavior of the a-and -aminoheteroeycles may be represented by 2-aminopyridine which is unreactive in acetic acid, slightly reactive in water, and quite reactive in pyridine (10). For amines of this basicity (11), lack of reaction would result from the formation of the resonating ion in acetic acid.…”

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confidence: 99%

SULFONAMIDE PREPARATIONS IN GLACIAL ACETIC ACID¹

Shepherd¹

1947

J. Org. Chem.

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The preparation of K1-halophenyl-N4-acetylsulfanilamides in the usual media, pyridine (1) and dimethylaniline (2), was found to be accompanied by undesirable side-reactions. This communication reports the results of an investigation of sulfonamide synthesis carried out in these and other media in an effort to overcome this difficulty. In particular, the scope of application of glacial acetic acid and its limitations with respect to this synthesis will be presented.Interest in the sulfanilanilides was aroused by the reported (IC) activity of the 3',5'-dihalo derivatives in a malarial infection in canaries and this work was undertaken in order to prepare a series of sulfonanilides for antimalarial investigation. The 3', 5'-dihalosulfanilanilides were found to possess activity which was retained in the presence of p-aminobenzoic acid when tested against a Plasmodium Eophurae infection in the duck. This was in marked contrast to other sulfanilamides (3) such as sulfadiazine. Another contrasting Characteristic was their activity against a Plasmodium cathemerium infection in the duck where the usual sulfanilamides are relatively inactive. The details of this work and the activity of a series of sulfonanilides against these two experimental malarial infections are being reported elsewhere (4).The side-reactions in pyridine, in pyridine-acetone or in dimethylaniline were most troublesome with haloanilines. For example, the tenacity of the contaminants is illustrated by the fact that colorless products of sharp melting point showed ultraviolet fluorescence not characteristic of later preparations by a different method. Consideration of the base strength of aniline in glacial acetic acid ( 5 ) and the ready acylation of anilines in this solvent (6) suggested its examination as a medium for the preparation of sulfonamides. Since this work was completed, certain preparations in acetic acid have been reported by Allen et al. (7). X-Acetylsulfanilyl chloride was found to have high solubility (footnote b, Table I) in boiling acetic acid and to be stable to the one-half per cent of water present. In contrast to the rapid decomposition of sulfonyl chlorides in pyridine solution, one mole of added water produced only a slow reaction in hot acetic acid as evidenced by the high recovery of N-acetylsulfanilyl chloride. However, the presence of bases such as sodium acetate or pyridine caused very rapid hydrolysis of the sulfonyl chloride in acetic acid while the effect of acetamide or urea was distinctly less rapid. These results are in general agreement with the base strengths (5) in this medium and with the assumption of an acetate

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Sulfanilyl Derivatives of Pyridine and Quinoline Amines

Cited by 12 publications

References 0 publications

Liquid-phase combinatorial synthesis.

Liquid-phase combinatorial synthesis.

Stucture and Chemotherapeutic Activities of Sulfanilamide Derivatives.

SULFONAMIDE PREPARATIONS IN GLACIAL ACETIC ACID¹

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Sulfanilyl Derivatives of Pyridine and Quinoline Amines

Cited by 12 publications

References 0 publications

Liquid-phase combinatorial synthesis.

Liquid-phase combinatorial synthesis.

Stucture and Chemotherapeutic Activities of Sulfanilamide Derivatives.

SULFONAMIDE PREPARATIONS IN GLACIAL ACETIC ACID1

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SULFONAMIDE PREPARATIONS IN GLACIAL ACETIC ACID¹