Acediasulfone

Acediasulfone

Systematic (IUPAC) name
2-([4-(4-aminophenyl)sulfonylphenyl]amino)acetic acid
Identifiers
CAS Number	80-03-5
ATC code	None
PubChem	CID 66451
ChemSpider	59823
UNII	30YP2YHH8W
ChEMBL	CHEMBL48396
Chemical data
Formula	C14H14N2O4S
Molar mass	306.337 g/mol
SMILES C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NCC(=O)O
InChI InChI=1S/C14H14N2O4S/c15-10-1-5-12(6-2-10)21(19,20)13-7-3-11(4-8-13)16-9-14(17)18/h1-8,16H,9,15H2,(H,17,18) Key:FKKUMFTYSTZUJG-UHFFFAOYSA-N
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Acediasulfone (INN) is an antimicrobial drug, which also has antimalarial activity. It is a long-acting prodrug of dapsone, which is used for treating leprosy.

Synthesis

Dapsone is somewhat inconvient to administer to patients because of its rather low water solubility.

Acediasulfone synthesis:^[1] CH 254803  and CH 278482  (1949, 1952, to Cilag Ltd.); Rawlins, U.S. Patent 2,589,211 (1952 to Parke Davis).

In the search for more easily administered drugs, 1 was reacted with bromoacetic acid to give acediasulfone (3) which can be adminsistered as a water soluble salt.

References

1. Jackson, Ernest L. (1948). "Certain N-Alkyl, N-Carboxyalkyl and N-Hydroxyalkyl Derivatives of 4,4'-Diamino-diphenyl Sulfone". Journal of the American Chemical Society 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.