Synthesis of Flavin-Calix[4]arene Conjugate Derivatives

The synthesis of two new flavin substituted calix[4]arene derivatives, 9 and 10, is described. The first flavin substituted calix[4]arene derivative 9 was synthesized by the reaction of 3-methylalloxazine (5) with 25,27-bis(3-bromopropoxy)-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl) calix[4] arene (4) in high yield (92%). The other derivative 10 was prepared from 3-methylalloxazine-1-acetic acid (7) and 25,27-bis(3-cyanopropoxy)calix[4]arene (3). All new compounds were characterized by a combination of FTIR and H-1-NMR spectroscopy, and elemental-analysis techniques.