Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• neuronal cells. Keywords: calcium mobilization; cIDPR analogues; cyclic ADP-ribose (cADPR); cyclization; Introduction Nucleosides and nucleotides (NNs) are widely used as key intermediates and important core structures in the field of synthetic medicinal chemistry [1][2]. They represent versatile

• synthesis of a variety of cIDPR analogues. In particular, the N1, N9 and C8-substituted cIDPR were the most interesting [24][25][26][27][28][29][30][31][32][33]. In the last few years several cIDPR analogues were also synthesized in our laboratory [34][35][36][37]. Among these, the N1-pentyl analogue cpIDP

• transient increase of intracellular concentration of Ca2+ when added to the cells, thus demonstrating their ability to cross the plasma membrane. Results and Discussion Chemistry The key step for the preparation of all cADPR/cIDPR analogues is the macrocyclization via pyrophosphate bond formation, which is