Pyrrolo[2,1-c][1,2,4]triazines from 2-diazopyrroles: synthesis and antiproliferative activity.
Pyrrolo[2,1-c][1,2,4]triazines 4a-g were directly obtained from the reaction of 2-diazopyrroles 1a and b with the sodium salts of beta-diketones, beta-carbonitriles, and beta-dinitriles. Only when the 2-diazopyrroles were coupled with ethyl cyanoacetate, it was possible to isolate, together with the pyrrolotriazines, the intermediate hydrazones 3 which, in turn, cyclised to the title ring system. Pyrrolotriazines 4a-e were evaluated for cytotoxic activity against a panel of 60 human cancer cell lines by the National Cancer Institute and some of them demonstrated inhibitory effects in the growth of a wide range of cancer cell lines generally at 10(-5) M level and in some cases at micromolar concentrations.
Diana
Patrizia
P
Dipartimento Farmacochimico Tossicologico e Biologico dell'Università, Via Archirafi 32, 90123 Palermo, Italy.
Barraja
Paola
P
Lauria
Antonino
A
Montalbano
Alessandra
A
Almerico
Anna Maria
AM
Dattolo
Gaetano
G
Cirrincione
Girolamo
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000627:therapeutic use; D002455:Cell Division / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000627:therapeutic use; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D011758:Pyrroles