Sulfonamide derivatives

Special mention obviously must be given to sulfonamide derivatives of the thiazole ring. A complete coverage of the field is beyond the scope of this review however, some examples of their activity may be given here ... 

Sulfonamides derived from sulfanilamide (p-arninoben2enesulfonainide) are commonly referred to as sulfa dmgs. Although several dmg classes are characterized by the presence of a sulfonamide function, eg, hypoglycemics, carbonic anhydrase inhibitors, saluretics, and tubular transport inhibitors, the antibacterial sulfonamides have become classified as the sulfa dmgs. Therapeutically active derivatives are usually substituted on the N nitrogen the position is generally unsubstituted. These features are illustrated by the stmctures of sulfanilamide (1) and sulfadiazine (2)... 

Thiadiazole, 2-amino-5-methyl-melting point, 6, 555 sulfonamide derivatives... 

Tosyl azide reacts differently to give sulfonamide derivatives 134). The morpholine enamine from dibenzylketone (196) for instance reacted with tosylazide to give 197 and phenyldiazomethane (198), which was trapped with acetic acid giving benzyl acetate 134). 

The initial studies of LSDAs were carried out with oleochemicals because of their structural similarity to soap. However, since the molecular structure of an efficient LSDA is characterized by a bulky hydrophilic polar head attached to a long hydrophobic tail, it is also possible to prepare LSDAs from petrochemicals. Sulfated sulfonamide derivatives of alkylbenzenes, such as commercially available detergent alkylates, were synthesized as follows [17] ... 

Palladium-catalysed asymmetrie allylations of various carbonyl compounds have been studied by Hiroi et al. using various types of chiral sulfonamides derived from a-amino acids. In particular, the chiral bidentate phosphinyl sulfonamide derived from (5)-proline and depicted in Scheme 1.63 was employed in the presence of palladium to eatalyse the allylation of methyl aminoacetate diphenyl ketimine with allyl aeetate, leading to the eorresponding (7 )-product with a moderate enantioseleetivity of 62% ee. This ligand was also applied to the allylation of a series of other nueleophiles, as shown in Seheme 1.63, providing the eorresponding allylated produets in moderate enantioseleetivities. 

A number of other bis(sulfonamides) derived from tran.s-l,2-diaminocyclo-hexane have been developed by several groups and successfully applied to these reactions. Thus, Walsh et al. have reported the use of a series of these ligands in the enantioselective addition of ZnEt2 to benzaldehyde giving excellent enan-tioselectivities, as shown in Scheme 3.39. ... 

Among various amino alcohols used as ligands, derivatives of simple and easily available carbohydrates are only rarely reported and remain underestimated. In this context, a-hydroxy sulfonamides derived from D-glucosa-mine have been used by Bauer et al. for addition of ZnEt2 to aldehydes, providing the corresponding products in high enantioselectivities of up to 97% ee, as shown in Scheme 3.47. ... 

On the other hand, several examples of chiral sulfonamides derived from ehiral a-amino acids have been successfully employed as ligands for enantio-seleetive Diels-Alder reactions. Thus, Yamamoto and Takasu have easily prepared new chiral Lewis acids from borane and sulfonamides of various ehiral a-amino acids, which were further studied for their abilities to promote the enantioselective Diels-Alder reaction between methacrolein and 2,3-dime-thyl-1,3-butadiene. Since 2,4,6-triisopropylbenzenesulfonamide of a-amino-butyric acid gave the highest enantioseleetivity, this eatalyst was applied to the... 

Similar reactions were also developed by Helmchen et al. using sulfonamides derived from L-valine." Among Lewis acids such as borane, dialkylaluminum... 

Several catalytic systems have been reported for the enantioselective Simmons Smith cyclopropanation reaction and, among these, only a few could be used in catalytic amounts. Chiral bis(sulfonamides) derived from cyclo-hexanediamine have been successfully employed as promoters of the enantioselective Simmons-Smith cyclopropanation of a series of allylic alcohols. Excellent results in terms of both yield and stereoselectivity were obtained even with disubstituted allylic alcohols, as shown in Scheme 6.20. Moreover, this methodology could be applied to the cyclopropanation of stannyl and silyl-substituted allylic alcohols, providing an entry to the enantioselective route to stannyl- and silyl-substituted cyclopropanes of potential synthetic intermediates. On the other hand, it must be noted that the presence of a methyl substituent at the 2-position of the allylic alcohol was not well tolerated and led to slow reactions and poor enantioselectivities (ee<50% ee). ... 

Saleh, M. and Pok, F., Separation of primary and secondary amines as their sulfonamide derivatives by reversed-phase high-performance liquid chromatography, /. Chromatogr. A, 763, 173, 1997. 

NVP—see NVP SJS APV, f-APV, TPV—sulfonamide derivative, potential for cross-reactivity with other sulfa drugs EFV—t incidence in children... 

Moy FJ, Chanda PK, Chen JM, Cosmi S, Edris W, Skotnicki JS, Wilhelm J, Powers P. NMR solution structure of the catalytic fragment of human fibroblast collagenase complexed with a sulfonamide derivative of a hydroxamic acid compound. Biochemistry 1999 38 7085-7096. 

Polytopic macrocyclic receptors 1, 2 (Figure 10.1) are able to complex the zwitterionic form of the amino acids by a double non-covalent charge interaction [28,29]. The unsymmetrical benzocrown sulfonamide derivative, 2 which contains benzo-18-crown-6 and benzo-15-crown-5 moieties was used as a ditopic receptor for multiple molecular recognition of the amino acids, by combining two non-covalent interactions ammonium-crown hydrogen bonding and carboxylate- complexed Na+-benzo-15-crown-5 charge interactions [28,33]. 

The reaction of diethylzinc or dimethylzinc with prochiral ketones, in the presence of a stoichiometric amount of Ti(OPr )4 and a catalytic amount (20%) of camphor-sulfonamide derivative 136, leads to the formation of the corresponding tertiary alcohols with enantiomeric ratios of up to 94.5 5.5. 

With sulfonamide-derived chloramine salts bearing smaller organic substituents on the sulfur, for example, methanesulfonamide-derived chloramine salt 111 (chloramine-M) as the oxidant, better results are obtained. This reagent can be prepared separately and added to the reaction mixture as the stable anhydrous... 

Sulfonamide derivatives of a-amino acids and the similar bissulfonamide derivatives of diamines can be used to prepare reactive Lewis acid complexes. Corey20 reported the Lewis acid (R,R)- or (5,5 )-complex 69, which can be employed at 10 mol% level to catalyze the Diels-Alder reaction of cyclopentadiene and imide. Reactions catalyzed by this complex give an endo.exo ratio of over 50 1, as well as a high ee (91%) at —78°C, and this can be further improved to 95% by carrying out the reaction at 90°C.20 The related aluminum complex 69b shows very similar reactivity at —78°C, with generally higher ee values, typically over 95%, for the reaction of cyclopentadiene derivatives with imide.20,21... 

Amino-l,5-diphenyltriazole is deaminated by diazotization in ethanolic solution and warming. 1-Aminotriazoles are deaminated in high yield by treatment with nitrous acid. Removal of a toluene-p-sulfonamido group can be accomplished in two steps by acid hydrolysis followed by diazotization, or in one step by treatment of the 1-toluene-p-sulfonamide derivative with sodium in liquid ammonia. ... 

Ammonium dinitramide has been synthesized from the nitration of ammonium sulfamate with strong mixed acid at -35 to -45 °C followedby neutralization of the resulting dinitraminic acid with ammonia. The yield is 45 % when the mole ratios of sulfuric acid to nitric acid is 2 1 and ammonium sulfamate to total acid is 1 6. The nitration of other sulfonamide derivatives, followed by hydrolysis with metal hydroxides, also yields dinitramide salts. ... 

Finn, A., Hollinshead, R., Khan, N. et al. (2005) Novel sulfonamide derivatives as inhibitors of histone deacetylase. Helvetica Chimica Acta, 88, 1630-1657. 

Anuria renal decompensation hypersensitivity to thiazides or related diuretics or sulfonamide-derived drugs hepatic coma or precoma (metolazone). 

Cross-sensitivity Cross-sensitivity between antibacterial sulfonamides and sulfonamide derivative diuretics, including acetazolamide and various thiazides, has been reported. 

Furosemide, torsemide, and bumetanide are sulfonamide derivatives, hence chemically related to the thiazides. They share the thiazides adverse effects of serum uric acid elevation and diabetogenic potential. Ethacrynic acid (Edecrin) is chemically unrelated to other diuretics and does not appear to have diabetogenic potential. 

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