Synthesis and biological activity of amides of 28-methoxy-28-oxo-1-cyano-2, 3-seco-lup-20(29)-en-3-oic acid

摘要

New A-seco-lupane C-3 amide conjugates were prepared by the reaction of 28-methoxy-28-oxo-1-cyano- 2, 3-seco-lup-20(29)-en-3-oic acid chloride with primary amines and synthetic and natural amino acids. Ethyl-N-[28-methyl-28-oxo- 1-cyano-2, 3-seco-lup-20(29)-en-3-oyl]β-alaninate, which was cytotoxic against rhabdomyosarcoma tumor cells (IC50 47.5 -M), in addition to ethyl-N-[28-methoxy-28-oxo-1-cyano-2, 3- seco-lup-20(29)-en-3-oyl]glycinate and N-[28-methyl-28-oxo-1-cyano-2, 3-seco-lup-20(29)-en-3-oyl]-2- aminothiazole, which inhibited reproduction of herpes simplex virus type 1 (EC50 35.1 and 30.9 -M, respectively), were selected.