Synthesis of (2R,3S)-2-(3,4-Dihydroxy phenyl)chroman-3,5,7-triol Derivative Boron Compounds: Antioxidant, Enzyme, Antimicrobial, and Antibiofilm Activities

(2R,3S)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol compound corresponds to catechin, which is from the flavanol class of flavonoids and has many pharmacological effects such as anticarcinogenic, antioxidant, dermatological, antihypertensive, antiviral, antimutagenic, antidiabetic. The aim of this study is to investigate novel drug candidates for several human diseases composed of catechin and boronic acid derivatives. Catechin was modified by various types of boronic acid compounds. In the derivatization experiment, phenyl boronic acid, 6-methoxy naphthalene boronic acid, 1,4-phenyl diboronic acid, 3-formyl phenyl boronic acid, and 4-methoxy-3-formyl phenyl boronic acid, 4-methoxy phenyl boronic acid were firstly used to modify catechin. The newly obtained compounds were structurally elucidated by 1H NMR, 13C NMR, FTIR, and LC-MS spectral techniques. All novel derivatives were examined for antioxidant (with particular methods such as ABTS, DPPH, and CUPRAC), enzyme, and antibiofilm activities. Most compounds were determined to be more active or effective than those standard compounds. Among all derivatives, CB-2 showed the highest inhibition of enzymes and the highest antioxidant activities. Biological results revealed that the boronic-modified compounds could be designed as potential antioxidants, enzymes, antimicrobials, and antibiofilm agents.