Synthesis of a novel prodrug of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoic acid for colon delivery

Massimo Curini; Francesco Epifano; Salvatore Genovese

doi:10.1016/j.bmcl.2005.07.088

Synthesis of a novel prodrug of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoic acid for colon delivery

Bioorg Med Chem Lett. 2005 Nov 15;15(22):5049-52. doi: 10.1016/j.bmcl.2005.07.088.

Authors

Massimo Curini¹, Francesco Epifano, Salvatore Genovese

Affiliation

¹ Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Via del Liceo, 06123 Perugia, Italy. curmax@unipg.it

PMID: 16165357
DOI: 10.1016/j.bmcl.2005.07.088

Abstract

A novel high-yielding and environment-friendly synthesis of the anticancer compound 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoic acid is described. This compound was conjugated to H2N-Ala-Pro dipeptide to give a prodrug to be activated by intestinal ACE and to be used in the treatment of different forms of colon cancer. Data on the chemical and enzymatic stability of this novel prodrug are reported.

Publication types

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

MeSH terms

Colon / drug effects
Colon / metabolism*
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / pharmacology*
Molecular Structure
Prodrugs / administration & dosage*
Prodrugs / chemical synthesis*
Prodrugs / chemistry
Prodrugs / pharmacology
Propionates / chemical synthesis*
Propionates / chemistry
Propionates / pharmacology*

Substances

3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans-propenoic acid
Diterpenes
Prodrugs
Propionates