Synthesis and biological evaluation of a conformationally free seco-analogue of the immunosuppressant FR901483

J Bonjoch; F Diaba; G Puigbó; D Solé; V Segarra; L Santamaría; J Beleta; H Ryder; J M Palacios

doi:10.1016/s0968-0896(99)00250-3

Synthesis and biological evaluation of a conformationally free seco-analogue of the immunosuppressant FR901483

Bioorg Med Chem. 1999 Dec;7(12):2891-7. doi: 10.1016/s0968-0896(99)00250-3.

Authors

J Bonjoch¹, F Diaba, G Puigbó, D Solé, V Segarra, L Santamaría, J Beleta, H Ryder, J M Palacios

Affiliation

¹ Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Spain. bonjoch@farmacia.far.ub.es

PMID: 10658593
DOI: 10.1016/s0968-0896(99)00250-3

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Division / drug effects
Humans
Immunosuppressive Agents / chemical synthesis*
Immunosuppressive Agents / chemistry
Immunosuppressive Agents / pharmacology*
In Vitro Techniques
Lymphocytes / cytology
Lymphocytes / drug effects
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Organophosphorus Compounds / chemical synthesis*
Organophosphorus Compounds / chemistry
Organophosphorus Compounds / pharmacology*
Structure-Activity Relationship

Substances

FR 901483
Immunosuppressive Agents
Organophosphorus Compounds