Synthesis and cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework.

Abstract

The synthesis of a family of rebeccamycin analogues in which one indole unit has been replaced by a 7-azaindole moiety is described.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.

• Authors: Samir Messaoudi, Fabrice Anizon, Stéphane Léonce, Alain Pierré, Bruno Pfeiffer, Michelle Prudhomme
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 40 Issue 10 Pg. 961-71 (Oct 2005) ISSN: 0223-5234 [Print] France
• PMID: 15907347 (Publication Type: Journal Article)

Chemical References

• Carbazoles
• Carbohydrates
• Imides
• Indoles
• carbazole
• rebeccamycin
• Nitrogen

Topics

• Animals
• Carbazoles (chemical synthesis, chemistry, toxicity)
• Carbohydrates (chemistry)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Humans
• Imides (chemistry)
• Indoles (chemical synthesis, chemistry, toxicity)
• Mice
• Molecular Structure
• Nitrogen (chemistry)
• Structure-Activity Relationship