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Sulfanilic Acid‐, Benzenedisulfonic Acid‐, and Naphthalenetrisulfonic Acid Analogues
Author(s) -
Kreimeyer Annett,
Müller Guido,
Kassack Matthias,
Nickel Peter,
Gagliardi Antonio R. T.
Publication year - 1998
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/(sici)1521-4184(199803)331:3<97::aid-ardp97>3.0.co;2-f
Subject(s) - chemistry , sulfanilic acid , suramin , benzimidazole , phosgene , moiety , yield (engineering) , chloride , organic chemistry , stereochemistry , bicyclic molecule , biochemistry , in vitro , materials science , metallurgy
The synthesis of suramin analogues bearing a 2‐phenyl‐benzimidazole moiety is described. Aminoarene sulfonic acids 2a–e are acylated with 3,4‐dinitrobenzoyl chloride 3 yielding the amides 4a‐e which are hydrogenated to the corresponding diamines 5a‐e . These are treated with 3‐nitrobenzaldehyde, yielding the azomethines 7a‐e and their isomers 8a‐e and 9a‐e . Key step in the synthesis of the target compounds 12a‐e is the oxidation of the azomethines with oxygen to the benzimidazoles 10a‐e . These are hydrogenated to the amines 11a‐e reacting with phosgene to yield the symmetric ureas 12a‐e . Results of the anti‐HIV, cytostatic, and antiangiogenic screening are presented.