Discovery of <i>meta</i>-Amido Bromophenols as New Antitubercular Agents

Abstract

A series of meta-amido bromophenol derivatives were designed and synthesized. The compounds were found to potently inhibit the growth of Mycobacterium tuberculosis H37Ra. They also exhibited moderate inhibitory activity against Mycobacterium tuberculosis H37Rv and multidrug-resistant strains. The compounds did not show inhibitory activity against normal Gram-positive and Gram-negative bacteria. Moderate cytotoxicities and good metabolic stability were observed for the selected compounds. The results demonstrated meta-amido bromophenols as a new class of antitubercular agents with good potentials.

Progress of Bromophenols in Marine Algae from 2011 to 2020: Structure, Bioactivities, and Applications

“…A series of meta -amido BPs have been designed and synthesized in recent years, which had good inhibitory effects on mycobacterium tuberculosis bacteria and multidrug resistant strains [ 101 ]. Compounds 4.10–4.13 ( Scheme 4 ) all showed powerful inhibition against the growth of mycobacterium tuberculosis bacteria H37Ra strain ( Table 4 ; MIC = 0.25–12.5 μg/mL), while they could not inhibit normal Gram-positive and Gram-negative bacteria, indicating their high specificity in the inhibition of tubercle bacillus.…”

“…Compounds 4.12 and 4.13 also exhibited moderate inhibitory activity against MDR-TB strains of Mycobacterium tuberculosis . Furthermore, these BPs showed good metabolic stability in rat livers [ 101 ]. Considering the above results, meta -amido BPs can become a novel type of anti-tubercular agents.…”

Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions

“…meta -Aminophenol derivatives are frequently used in pharmaceutical science ( Figure 1 ) [ 1 , 2 , 3 , 4 , 5 ]. For example, SEA0400 exhibits inhibitory activity on the Na + /Ca 2+ exchanger [ 1 ], while tetrapetalone A [ 2 ] and tenaspimycin [ 3 ] inhibit lipoxygenase and Hsp90, respectively.…”