PMID: 11312925Apr 21, 2001Paper

New selective cytotoxic diterpenylquinones and diterpenylhydroquinones

Journal of Medicinal Chemistry
José M Miguel Del CorralArturo San Feliciano

Abstract

A new series of diterpenylquinone/hydroquinones has been prepared by Diels-Alder cycloaddition between three labdanic diterpenoids (myrceocommunic acid, methyl myrceocommunate, and myrceocommunyl acetate) and p-benzoquinone or 1,4-naphthoquinone. Influences of the quinone/hydroquinone fragment and other structural features, such as the different functionalities in the terpenic core, are considered in relation to the cytotoxicity toward neoplastic cells and the selectivity of these diterpenylnaphthoquinones/hydroquinones and anthraquinones. Several compounds showed IC50 values under the micromolar level, and four of these derivatives were evaluated at the NCI screening panel. The results showed an important selectivity toward renal cancer lines, identifying these compounds as a very promising group of antineoplastics.

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Citations

Feb 23, 2002·European Journal of Medicinal Chemistry·Aurora MolinariArturo San Feliciano
Mar 14, 2012·Marine Drugs·Marina Gordaliza
May 15, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joan VillenaLuis Espinoza
Jul 21, 2004·Il Farmaco·Aurora MolinariArturo San Feliciano
Oct 27, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dusan Sladić, Miroslav J Gasić
Sep 14, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luis Espinoza CatalánKaren Catalán Marín
Feb 9, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luis Espinoza CatalánMaría Cristina Chamy
Sep 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luis Espinoza CatalánJoan Villena García
Apr 5, 2008·Archiv der Pharmazie·Aurora MolinariArturo San Feliciano
Aug 24, 2018·Marine Drugs·Pablo A GarcíaMª Ángeles Castro
Nov 5, 2019·International Journal for Parasitology. Drugs and Drug Resistance·Yolanda Pérez-PertejoMaría-Ángeles Castro
Jan 23, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ángela P HernándezMª Ángeles Castro
Apr 29, 2021·Chemical Communications : Chem Comm·Thomas Varlet, Géraldine Masson
Apr 20, 2018·ACS Medicinal Chemistry Letters·Ángela P HernándezMa Ángeles Castro
Oct 10, 2002·Journal of the American Chemical Society·Taotao LingEmmanuel A Theodorakis

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