Direct metallation of thienopyrimidines using a mixed lithium-cadmium base and antitumor activity of functionalized derivatives

Katia Snégaroff (1) , Frédéric Lassagne (1) , Ghenia Bentabed-Ababsa (1, 2) , Nassar Ekhlass (3) , Ely Sidaty Cheikh Sid (1) , Stéphanie Hesse (4) , Enrico Perspicace (4) , Aïcha Derdour (2) , Florence Mongin (5)

1 CPM - Chimie et Photonique Moléculaires
2 Laboratoire de Synthèse Organique Appliquée
3 ASU - Ain Shams University
4 LIMBP - Laboratoire d'Ingéniérie Moléculaire et Biochimie Pharmacologique
5 ISCR - Institut des Sciences Chimiques de Rennes

A series of thieno[2,3-d]- and thieno[3,2-d]pyrimidines have been easily synthesized using as key step a deproto-cadmiation-trapping sequence. Some of the compounds thus synthesized were screened for anti-cancer (cytotoxic) activities, and (S)-2-(6-iodo-2-phenylthieno[2,3-d]pyrimidin- 4-ylamino)-3-phenylpropanoic acid proved to have a significant activity towards liver, human breast and cervix carcinoma cell lines.

Domaines: Chimie organique

Katia Snégaroff, Frédéric Lassagne, Ghenia Bentabed-Ababsa, Nassar Ekhlass, Ely Sidaty Cheikh Sid, et al.. Direct metallation of thienopyrimidines using a mixed lithium-cadmium base and antitumor activity of functionalized derivatives. Organic & Biomolecular Chemistry, 2009, 7 (22), pp.4782-4788. ⟨10.1039/B915274A⟩. ⟨hal-00785054⟩