Aza-analogues of the marine pyrroloquinoline alkaloids wakayin and tsitsikammamines: synthesis and topoisomerase inhibition.
Two aza-analogues of the marine pyrroloquinoline alkaloids wakayin and tsitsikammamines A and B have been synthesized. The strategy used was based on a 1,3-dipolar cycloaddition reaction between indole 4,7-dione and a diazo-aminopropane derivative. One of the two analogues partially inhibits human topoisomerase I, whereas synthetic intermediates inhibit the enzyme DNA cleavage activity at a concentration comparable to that of the control drug camptothecin.
Legentil
Laurent
L
Laboratoire SPCMIB, UMR-CNRS 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cédex 4, France.
Lesur
Brigitte
B
Delfourne
Evelyne
E
D000818:Animals; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D006801:Humans; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D059004:Topoisomerase I Inhibitors
D001372:Aza Compounds; D026121:Indole Alkaloids; D011758:Pyrroles; D011804:Quinolines; D059004:Topoisomerase I Inhibitors; C410406:pyrroloquinoline; C508209:tsitsikammamine A; C508210:tsitsikammamine B; C508208:wakayin