4- Aminobenzene sulfonamide

In their synthesis of potential antipsychotic agent analogues, Navas et al. used 2-aminobenzene sulfonamide 30 to open the azoniaspirodecane bromide 29 (Equation 8) <1998BMC811>. 

ChlorO 7-methoxyna ph-thalene-l-snlfonamide 2 Aminobenzene sulfonamide... 

In 1935, his daughter Hildegarde developed a severe septicemia after pricking her finger with a needle, and her life was saved by protonsil rubrum. It turned out that the azo link in this red dye was cleaved in the patient s body to form colorless 4-aminobenzene sulfonamide, which is really the active principle. This led to... 

The mode of action of sulfanilamides became known around 1947, when the structure and biosynthesis of folic acid were elucidated. This compound is built by bacteria from the heterocyclic pteroyl moiety, p-aminobenzoate, and glutamate. p-Aminobenzene-sulfonamide (9.89, sulfanilamide) is a competitive inhibitor of the synthase enzyme, acting as an antimetabolite of p-aminobenzoate. Occasionally, the sulfanilamide can even be incorporated into the modified folate, resulting in an inactive compound and thus an inactive enzyme. This theory, proposed by Woods and Fildes in 1940, became the first molecular explanation of drug action. 

SYNS ALBEXAN ALBOSAL AMBESIDE p-.UIINOBENZENESULFAMIDE p-AMINO-BENZENESULFONAMIDE 4-AMINOBENZENE-SULFONAMIDE p-AMINOPHENYLSULFONAMIDE 4-AMINOPHENYLSULFONAMIDE p-ANILINE-SULFONAMIDE ANILINE-p-SULFONIC AMIDE ANTISTREPT BACTERAMID COLLOMIDE COLSULANYDE COPTICIDE DIPRON ESTREPTOCEDA F 1162 FOURNEAU 1162 GERISON GOMBARDOL LUSIL LYSOCOCCINE... 

The second is a comparably contemporary study94 on both the parent p-aminobenzene-sulfonamide and p-amino-fV-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide, known in the medicinal community as sulfanilamide and sulfisoxazole, respectively. As solids, the enthalpies of formation are —458.3 1.6 and —180.1 3.8 k.l mol 1, respectively. The former species may be compared with benzenesulfonamide, for which we cite only the most recent enthalpy of formation95, —320.1 1.6 k.l mol 1. As has been so often the case, we cannot reconcile the two sets of values. We are immediately thwarted in the comparison of the latter species. We lack the desired data for the desamino species or for any isoxazolamine-containing species. 

The classic case is that of Prontosil (Figure 7.1) in which the compound is active against bacterial infection in animals although inactive against the bacteria in pure culture. The toxicity in animals is the result of reduction to the sulfanilamide (4-aminobenzene-sulfonamide) that competitively blocks the incorporation of 4-ami-nobenzoate into the vitamin folic acid. 

Sulfonamides are known for their abihty to form antibacterial drugs, and the derivatives of 4-aminobenzene sulfonamide serve a number of medical apphcations. Analytical pyrolysis of these compounds proceeds in a manner similar to that of amino acids. 

FIGURE 9.7 Typical pH-responsive polyacids (a) poly(acrylic acid) (PAAc) (b) poly(methacrylic acid) (PMAAc) (c) poly(2-ethyl acrylic acid) (PEAAc) (d) poly(2-propyl acrylic acid) (PPAAc) (e) poly(methacrylic amide) contains p-aminobenzene sulfonamide. 

By heating the diacetyl compound with sodium hydroxide solution partial saponification of the acetyl groups takes place. 25.6 grams of diacetyl compound are heated to boiling for some hours with 100 cc of 2 N sodium hydroxide solution. The precipitate produced by acidification of the solution with acetic acid is filtered off and treated with dilute sodium carbonate solution. The 4-aminobenzene-sulfonacetylamide passes into solution while the simultaneously formed 4-acetylaminobenzene-sulfonamide remains undissolved. It is filtered with suction and the filtrate again acidified with acetic acid. The 4-aminobenzene-sulfon-acetamide separates out and is recrystallized from water. It forms colorless lustrous rhombic crystals Of MP 1B1°C. 

Chloroquinoxaline derivatives undergo facile nucleophilic displacement with am-amines,3tf>-38o hydrazine, - - with 4-aminobenzene-l-sulfonamide to give 2-[(4-aminophenyl)sulfonamido]quinoxaline, with alkoxides" or phenolates. -... 

Other problems of cross-reactivity frequently encountered include the aminoglycoside antibiotics (streptomycin, kanamycin, neomycin, gentamycin), the p-aminobenzene derivatives (sulfonamides, sulfonylureas, procaine, procainamide, thiazide, carbonic anhydrase inhibitors), local anesthetics containing the p-aminophenyl group, and iodinated contrast media. 

Sulfanilamide (CgHgN202S) = White, odorless crystalline sulfonamide, used in the treatment of various bacterial infections. Synonyms Albexan albosol ambeside p-aminobenzene sulfamide sulfanilamide purified bacteramid 4-amino-benzenesulfonamide. 

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