125744-14-1Relevant articles and documents
New antifolate 4,4'-diaminodiphenyl sulfone substituted 2,4-diamino-5-benzylpyrimidines. Proof of their dual mode of action and autosynergism
Wiese,Schmalz,Seydel
, p. 161 - 168 (2007/10/03)
New 4,4'-diaminodiphenylsulfone substituted 2,4-diamino-5-benzylpyrimidines were synthesized. These compounds are highly active inhibitors of both bacterial dihydrofolate reductase (DHFR) and dihydropteroic acid synthase (SYN). The simultaneous inhibition
Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase
-
, (2008/06/13)
Disclosed are substituted bis(4-aminophenyl-sulfonees of general formula STR1 wherein R1 is hydrogen, alkyl or cycloalkyl; group, R2 is hydrogen or C1 -C3 alkyl, R3 is nitrile, C1 -C3 alkylaminocarbonyl, di C1 -C3 alkylaminocarbonyl, C3 -C7 N-cycloalkyl-C1 -C3 alkylaminocarbonyl C1 -C3 alkylamino, C1 -C3, di alkylaminocarbonyl alkoxy, alkylaminosulfonyl, di C1 -C3 alkylaminono, diC1 -C3 alkylaminosulfonyl, hydroxy C1 -C3 alkyl, C1 -C3 alkylcarbonyl, amino C1 -C3 alkyl or C1 -C3 alkoxy C1 -C3 alkyl group or, when R1 and R2 are each hydrogen, R3 can be hydroxy, hydroxycarbonyl C1 -C3 alkoxy or di C1 -C3 aminocarbonylalkoxy; or, when R1 is C1 -C3 alkyl or C1 -C3 cycloalkyl and R2 is hydrogen or C1 -C3 alkyl, R3 can also be halogen, trifluoromethyl, nitro, amino, aminosulfonyl, aminocarbonyl, C1 -C3 alkylo, carboxy or C1 -C3 akoxycarbonyl; and R4 is hydrogen or, when R1 and R2 are each hydrogen and R3 is halogen or hydroxy, R4 can also be halogen, hydroxy or C1 -C3 alkoxy; or a nontoxic, pharmaceutically acceptable salt thereof. Also disclosed are pharmaceutical compositions comprising such compounds alone and in combination with dihydrofolic acid-reductage inhibitors. The compounds and compositions are useful for their inhibiting effect on bacteria, mycobacteria and plasmodia.
Preparation and biological activity of new substituted antimalarial diaminodiphenylsulfones
Pieper,Seydel,Kruger,Noll,Keck,Wiese
, p. 1073 - 1080 (2007/10/02)
Starting from 4,4'-diamino-diphenylsulfone (DDS) as a lead structure, new 2-substituted analogues as well as new 2-substituted 4-alkylamino-4'-amino diphenylsulfones have been designed and synthesized in different ways. This has led to compounds the inhibitory activity of which against 7,8-dihydropteroic acid synthase of plasmodia and mycobacteria is clearly superior to that of sulfadoxine and in most cases to that of DDS. Of special interest is 4'-amino-4-n-propylamino-2-methyl-diphenylsulfone. Together with inhibitors of 7,8-dihydrofolate reductase in vitro and in vivo it possesses a marked synergistic inhibitory activity against plasmodia. In contrast to DDS in doses up to 200 mg/kg p.o. (cat) no methemoglobin formation is observed. The compound has been selected for further studies.
Substituted bis-(4-aminophenyl)-sulfones
-
, (2008/06/13)
Disclosed are substituted bis(4-aminophenyl)-sulfones of general formula STR1 wherein R1 is hydrogen, alkyl or cycloalkyl; group, R2 is hydrogen or C1 -C3 alkyl, R3 is nitrile, C1 -C3 alkylaminocarbonyl, di C1 -C3 alkylaminocarbonyl, C3 -C7 N-cycloalkyl-C1 -C3 alkylaminocarbonyl C1 -C3 alkylamino, C1 -C3, di alkylaminocarbonyl alkoxy, alkylaminosulfonyl, di C1 -C3 alkylaminono, diC1 -C3 alkylaminosulfonyl, hydroxy C1 -C3 alkyl, C1 -C3 alkylcarbonyl, amino C1 -C3 alkyl or C1 -C3 alkoxy C1 -C3 alkyl group or, when R1 and R2 are each hydrogen, R3 can be hydroxy, hydroxycarbonyl C1 -C3 alkoxy or di C1 -C3 aminocarbonylalkoxy; or, when R1 is C1 -C3 alkyl or C1 -C3 cycloalkyl and R2 is hydrogen or C1 -C3 alkyl, R3 can also be halogen, trifluoromethyl, nitro, amino, aminosulfonyl, aminocarbonyl, C1 -C3 alkyl, carboxy or C1 -C3 alkoxycarbonyl; and R4 is hydrogen or, when R1 and R2 are each hydrogen and R3 is halogen or hydroxy, R4 can also be halogen, hydroxy or C1 -C3 alkoxy; or a nontoxic, pharmaceutically acceptable salt thereof. Also disclosed are pharmaceutical compositions comprising such compounds alone and in combination with dihydrofolic acid-reductase inhibitors. The compounds and compositions are useful for their inhibiting effect on bacteria, mycobacteria and plasmodia.
