PMID: 9557135Apr 29, 1998Paper

Suramin analogues with a 2-phenylbenzimidazole moiety as partial structure; potential anti HIV- and angiostatic drugs, 2: Sulfanilic acid-, benzenedisulfonic acid-, and naphthalenetrisulfonic acid analogues

Archiv der Pharmazie
A KreimeyerA R Gagliardi

Abstract

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.

Citations

Apr 10, 2004·European Journal of Medicinal Chemistry·Matthias U KassackGünter Lambrecht
Jan 22, 2004·The Journal of Biological Chemistry·Daniel F McCainZhong-Yin Zhang
Oct 28, 2005·Journal of Medicinal Chemistry·Heiko UllmannMatthias U Kassack

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