title: Synthesis of desaza analogues of annomontine and canthin-4-one alkaloids.
abstract: 1-Acetylcarbazoles are readily converted to 3-desazacanthin-4-ones upon treatment with Bredereck's reagent, but in contrast to canthin-4-ones, these do not undergo ring transformation reactions with guanidine. Only after N-protection (methyl or 2-(trimethylsilyl)ethoxymethyl group), 2-desaza analogues of the alkaloid annomontine are accessible via the enaminoketones obtained by condensation with Bredereck's reagent. One of the annomontine analogues is an inhibitor of the Plasmodium falciparum CDC-like kinases (CLK) and shows antimalarial activity.
authors: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians-University of Munich, Munich, Germany.
authors: Benjamin
authors: B
authors: Strödke
authors: André P
authors: AP
authors: Gehring
authors: Franz
authors: F
authors: Bracher
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D015195:Drug Design; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects* / Q000201:enzymology; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D017346:Protein Serine-Threonine Kinases / Q000037:antagonists & inhibitors / Q000378:metabolism; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors / Q000378:metabolism; D015800:Protozoan Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000962:Antimalarials; D002243:Carbolines; D047428:Protein Kinase Inhibitors; D015800:Protozoan Proteins; D011743:Pyrimidines; C508838:annomontine; C066780:Clk dual-specificity kinases; D011505:Protein-Tyrosine Kinases; D017346:Protein Serine-Threonine Kinases
keywords: Alkaloids; Antimalarial activity; Desaza analogues; Kinase inhibitor