Design and synthesis of analogues of ionomycin

Article abstract of DOI:10.1139/v94-187

Based on the analysis of the crystal structure of the Ca²⁺ salt of ionomycin and the chemical and physical data on ionomycin, a number of ionomycin analogues have been synthesized to study the structural features affecting the Ca²⁺ binding and transport. Compounds 2, 3, and 4 were synthesized to study the effect of additional intramolecular oxygen coordination sites on Ca²⁺ transport. Compounds 5a-5d were prepared to study the effect of lipid solubility on Ca²⁺ binding and transport. Compounds 6a-6c were prepared to study the effect of the distance between the β-diketone and the carboxyl group on Ca²⁺ transport. A general synthetic route to these compounds has been developed. The key reactions in this route are the consecutive regioselective alkylations of the dianion of 2,4-pentanedione with the appropriate bromides.