Synthesis of argentatin A derivatives as growth inhibitors of human cancer cell lines in vitro

Hortensia Parra-Delgado; Teresa Ramírez-Apan; Mariano Martínez-Vázquez

doi:10.1016/j.bmcl.2004.12.038

Synthesis of argentatin A derivatives as growth inhibitors of human cancer cell lines in vitro

Bioorg Med Chem Lett. 2005 Feb 15;15(4):1005-8. doi: 10.1016/j.bmcl.2004.12.038.

Authors

Hortensia Parra-Delgado¹, Teresa Ramírez-Apan, Mariano Martínez-Vázquez

Affiliation

¹ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Circuito Exterior, Coyoacán C. P. 04510, México, DF.

PMID: 15686901
DOI: 10.1016/j.bmcl.2004.12.038

Abstract

The syntheses of nine argentatin A analogs are described. These compounds were assessed for their ability to inhibit growth in vitro in four human cancer cell lines. Our results showed that the presence of either a double bond at C-1/C-2, or a bromine atom or formyl moiety at C-2 as well as the presence of an isoxazol ring in argentatin A enhanced its potency in all cell lines tested. In addition, an X-ray study of (16S,17R,20S,24R)-3-oxime-20,24-epoxy-16,25-dihydroxy-cycloartan-3-one led to the determination of the correct stereochemistry of argentatin A.

Publication types

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

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Cell Proliferation / drug effects*
Humans
Inhibitory Concentration 50
Molecular Structure
Triterpenes / chemical synthesis*
Triterpenes / pharmacology

Substances

Antineoplastic Agents
Triterpenes
argentatin A