Anionic polyhedral boron clusters conjugates with 7-diethylamino-4-hydroxycoumarin. Synthesis and lipophilicity determination

A series of water-soluble conjugates of 7-diethylamino-4-hydroxycoumarin with four different anionic polyhedral boron clusters was synthesized. The distribution coefficients (log D 7.4 ) as a measure of the ability to pass through the cell membrane for novel compounds were determined via a shake-flask methodology in n-octanol/aqueous (pH 7.4) buffer solution system. For two closo-dodecaborate modifications log D 7.4 displayed negative lipophilicity values. Conjugates of metallacarboranes containing Co and Fe as long as two 7,8-dicarba-nido-undecaborate coumarin anions were found to have appropriate lipophilicity for medicinal applications. (c) 2021 Elsevier B.V. All rights reserved.

Automated summary

A series of water-soluble conjugates of 7-diethylamino-4-hydroxycoumarin with four different anionic polyhedral boron clusters were synthesized and tested for their ability to pass through the cell membrane. The results showed two compounds with negative lipophilicity values, while conjugates of metallacarboranes containing Co and Fe were found to be suitable for medicinal applications.