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Pure Appl. Chem. Vol. 73, No. 9, pp. 1437-1444 (2001)

Pure and Applied Chemistry

Vol. 73, Issue 9


Retinoic acid and analogs as potent inducers of differentiation and apoptosis. New promising chemopreventive and chemotherapeutic agents in oncology*

Daniele Simoni1,#, Riccardo Rondanin1, Riccardo Baruchello1, Marinella Roberti2, Marcello Rossi1, Stefania Grimaudo3, Natale D'Alessandro4, Francesco Paolo Invidiata5, and Manlio Tolomeo3

1Dipartimento di Scienze Farmaceutiche, Via Fossato di Mortara 17-19, Università di Ferrara, 44100 Ferrara, Italy; 2Dipartimento di Scienze Farmaceutiche, Università di Bologna, Italy; 3Divisione di Ematologia e Servizio AIDS, Policlinico di Palermo, Italy; 4Dipartimento di Scienze Farmacologiche, Università di Palermo, Italy; 5Dipartimento Farmacochimico Tossicologico e Biologico, Università di Palermo, Italy

Abstract: In this report we will describe the preparation and the biological activity of a novel class of heterocyclic arotinoids endowed with potent cytotoxic and apoptotic acitivity. Structure­activity relationship studies revealed that the different stereochemistry at the C9 double bond of retinoids seems associated with a different biological activity: potent apoptotic activity for the cis-isomers, whereas differentiating activity for the trans structures. An interesting modified Wittig procedure that allows easily to arotinoids will also be described. The substitution of the alkenyl portion with a more flexible oxymethyl or aminomethyl moiety gave compounds with poor activity, whereas isoxazole-bridged arotinoids allowed compounds active also on multidrug-resistant (MDR) leukemia cell lines.

*Plenary lecture presented at the Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry, Budapest, Hungary, 2 –6 September 2001. Other presentations are published in this issue, pp. 1387-1509.
# Corresponding author.

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