Synthesis of bioactive sesterterpenolides from ent-halimic acid. 15-epi-ent-Cladocoran A and B

I S Marcos; A B Pedrero; M J Sexmero; D Diez; P Basabe; N García; R F Moro; H B Broughton; F Mollinedo; J G Urones

doi:10.1021/jo034663l

Synthesis of bioactive sesterterpenolides from ent-halimic acid. 15-epi-ent-Cladocoran A and B

J Org Chem. 2003 Sep 19;68(19):7496-504. doi: 10.1021/jo034663l.

Authors

I S Marcos¹, A B Pedrero, M J Sexmero, D Diez, P Basabe, N García, R F Moro, H B Broughton, F Mollinedo, J G Urones

Affiliation

¹ Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain.

PMID: 12968906
DOI: 10.1021/jo034663l

Abstract

The bioactive sesterterpenoid gamma-hydroxybutenolides 15,18-bisepi-ent-Cladocoran A and B, 1 and 2, and 15-epi-ent-Cladocoran A and B, 57 and 55, were synthesized from ent-halimic acid. The synthesized sesterterpenolids 2, 55, 57, and 59 inhibited cellular proliferation (IC(50) congruent with 2 micro M) of a number of human leukaemic and solid tumor cell lines.

Publication types

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

MeSH terms

4-Butyrolactone / analogs & derivatives
4-Butyrolactone / chemistry
4-Butyrolactone / pharmacology
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Cell Division / drug effects
Cell Line, Tumor
Humans
Inhibitory Concentration 50
Protein Tyrosine Phosphatases / antagonists & inhibitors
Sesterterpenes
Stereoisomerism
Structure-Activity Relationship
Terpenes / chemical synthesis*
Terpenes / pharmacology*

Substances

Antineoplastic Agents
Sesterterpenes
Terpenes
cladocoran A
Protein Tyrosine Phosphatases
dysidiolide
4-Butyrolactone