Synthesis and biological evaluation of a conformationally free seco-analogue of the immunosuppressant FR901483.
The synthesis of an azaspirocyclic analogue of FR901483, phosphate 2, is described based on the implementation of a key 5-endo aminocyclization promoted by iodine for direct functionalization of the 1-azaspiro[4.5]decane ring at the C-3 atom. Compound 2 has no inhibitory activity in the cell proliferation assays reported.
Bonjoch
J
J
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Spain. bonjoch@farmacia.far.ub.es
Diaba
F
F
Puigbó
G
G
Solé
D
D
Segarra
V
V
Santamaría
L
L
Beleta
J
J
Ryder
H
H
Palacios
J M
JM
D002455:Cell Division / Q000187:drug effects; D006801:Humans; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066298:In Vitro Techniques; D008214:Lymphocytes / Q000166:cytology / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
C098358:FR 901483; D007166:Immunosuppressive Agents; D009943:Organophosphorus Compounds