Substituted 2-Sulfanilamidopyrimidines

Abstract

The pharmacological activity and low toxicity of sulfapyrimidine2 have led us to continue3 the preparation of a number of higher homologs and related derivatives, some of which we wish to describe at this time. Five of the requisite substituted 2-aminopyrimidines were prepared by refluxing the appropriate hydroxymethylene ketones with guanidine carbonate in alcohol.4 R-C=0Na R-C=0

Liquid-phase combinatorial synthesis.

“…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.…”

“…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.…”

Synthesis of typical sulfonamide antibiotics with [14C]- and [13C]-labeling on the phenyl ring for use in environmental studies

“…The methods for purification described herein are appropriate for [ 14 C]-compounds produced in small amounts as they result in a high purity. Both crystallization in water, as a purification procedure, and the direct use of the reaction mixture without further purification are applicable to the synthesis of unlabeled SAs at a gram scale [ 26 , 27 ], but not to the synthesis of [ 14 C]-labeled SAs at a milligram scale, because impurities may affect the next reaction in the absence of purification, but recrystallization may result in the recovery of smaller amounts of product. In this study, we used classic chromatographic separation methods, such as flash column chromatography and preparative TLC, to purify small amounts of [ 14 C]-products.…”

Drugs Originating from the Screening of Dyes

“…Sulfadimidine is also known as sulfamezathine and was first synthesized at Temple University in Philadelphia by William Caldwell and two of his Masters students. 44 It had even greater solubility in urine than sulfadiazine, though it was less potent.…”