Synthesis and cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework.
The synthesis of a family of rebeccamycin analogues in which one indole unit has been replaced by a 7-azaindole moiety is described. Substitutions have been carried out on the imide nitrogen, on the carbazole framework and on the sugar part. Compounds with a lactam upper heterocycle have also been prepared. The cytotoxicities of the newly synthesized compounds toward four tumor cell lines, one murine leukemia (L1210) and three human tumor cell lines (prostate carcinoma DU145, colon carcinoma HT29, and non-small cell lung carcinoma A549) have been evaluated and compared to those of rebeccamycin and parent non-aza and aza compounds.
Messaoudi
Samir
S
Université Blaise Pascal, Synthèse et Etude de Systèmes à Intérêt Biologique, UMR 6504 du CNRS, 63177 Aubière, France.
Anizon
Fabrice
F
Léonce
Stéphane
S
Pierré
Alain
A
Pfeiffer
Bruno
B
Prudhomme
Michelle
M
D000818:Animals; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity*; D002241:Carbohydrates / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D007094:Imides / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D051379:Mice; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013329:Structure-Activity Relationship
D002227:Carbazoles; D002241:Carbohydrates; D007094:Imides; D007211:Indoles; C041514:carbazole; C053339:rebeccamycin; D009584:Nitrogen