Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone

N J Lawrence; A T McGown; J Nduka; J A Hadfield; R G Pritchard

doi:10.1016/s0960-894x(00)00686-7

Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone

Bioorg Med Chem Lett. 2001 Feb 12;11(3):429-31. doi: 10.1016/s0960-894x(00)00686-7.

Authors

N J Lawrence¹, A T McGown, J Nduka, J A Hadfield, R G Pritchard

Affiliation

¹ Department of Chemistry, UMIST, Manchester, UK. [email protected]

PMID: 11212128
DOI: 10.1016/s0960-894x(00)00686-7

Abstract

Two series of cytotoxic (IC50, K562 cell line, 1-24 microM) alpha-aminomethyl substituted lactones 3 and 4 were prepared by stereoselective Michael-type addition of amines to alantolactone (1) and isoalantolactone (2). The lactones 1 and 2 and their amine adducts induce apoptosis and act as alkylating agents.

Publication types

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

MeSH terms

Amines / chemistry*
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Apoptosis / drug effects
Cell Cycle / drug effects
Cell Division / drug effects
Combinatorial Chemistry Techniques
Humans
Inhibitory Concentration 50
K562 Cells
Lactones / chemical synthesis
Lactones / pharmacology*
Structure-Activity Relationship
Tumor Cells, Cultured / drug effects

Substances

Amines
Antineoplastic Agents
Lactones
methylene-lactone