Straightforward synthesis of bis-tetraazacycloalkanes: towards new potential CXCR4 antagonists?

Nicolas Sok (1, 2) , Isabelle Baglin (3) , Christelle Basset (4) , Fatima Fakkor (5) , Evelyne Kohli (4) , Yoann Rousselin (3) , Claire Bernhard (3) , Frédéric Boschetti (6) , Christine Goze (3) , Franck Denat (3)

1 PAM - Procédés Alimentaires et Microbiologiques [Dijon]
2 PCAV - Physico-Chimie de l'Aliment et du Vin
3 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]
4 LNC - Lipides - Nutrition - Cancer [Dijon - U1231]
5 CHU Dijon - Centre Hospitalier Universitaire de Dijon - Hôpital François Mitterrand
6 CheMatech - Macrocycle Design Technologies

We report herein an efficient and general method for the synthesis of new bismacrocyclic compounds, structural analogues of biscyclam AMD3100, in which the two macrocycles are linked together through carbon atoms of the cycles. Several representatives of this new class of biscyclic derivatives were prepared by reacting C-aminomethyl-13aneN4 with aromatic dialdehydes. Preliminary in vitro studies were performed to evaluate the affinity of these compounds towards the co-receptor CXCR4.

Keywords: Breast-cancer metastasis; Chemokine receptor cxcr4; Inhibitors; Amd3100; Complexes; Discovery; Story; Hiv-1

Domains: Chemical Sciences

Nicolas Sok, Isabelle Baglin, Christelle Basset, Fatima Fakkor, Evelyne Kohli, et al.. Straightforward synthesis of bis-tetraazacycloalkanes: towards new potential CXCR4 antagonists?. RSC Advances, 2017, 7 (45), pp.28291 - 28297. ⟨10.1039/c7ra04218c⟩. ⟨hal-01560414⟩