Novel homologated-apio adenosine derivatives as A3 adenosine receptor agonists: design, synthesis and molecular docking studies

Abstract

Synthesis of a series of novel homologated-apio adenosine analogues including homologated-apio IB-MECA and Cl-IB-MECA has been accomplished from a commercially available, inexpensive starting material D-ribose. The synthetic route includes a controlled oxidative cleavage of vicinal diol and Mitsunobu condensation reactions as the key steps. The molecular docking studies of the synthesized compounds to the A₃ adenosine receptor model indicated them as agonists. Interestingly, some of the molecules showed good binding interactions at the active site as evident by docking scores and MM/GBSA binding affinity.