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.
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.
Kreimeyer
A
A
Pharmazeutisches Institut, Universität Bonn, Germany.
Müller
G
G
Kassack
M
M
Nickel
P
P
Gagliardi
A R
AR
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001557:Benzenesulfonates / Q000138:chemical synthesis / Q000494:pharmacology; D002478:Cells, Cultured; D004353:Drug Evaluation, Preclinical; D006801:Humans; D009282:Naphthalenesulfonates / Q000138:chemical synthesis / Q000494:pharmacology; D013425:Sulfanilic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D013498:Suramin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D001557:Benzenesulfonates; D009282:Naphthalenesulfonates; D013425:Sulfanilic Acids; D013498:Suramin