Diverse Biological Activity of Benzofuroxan/Sterically Hindered Phenols Hybrids
Elena Chugunova1, Elmira Gibadullina1, Kirill Matylitsky1
1Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, 420088 Kazan, Russia.
Abstract:
Combining two pharmacophores in a molecule can lead to useful synergistic effects. Herein, we show hybrid systems that combine sterically hindered phenols with dinitrobenzofuroxan fragments exhibit a broad range of biological activities. The modular assembly of such phenol/benzofuroxan hybrids allows variations in the phenol/benzofuroxan ratio. Interestingly, the antimicrobial activity only appears when at least two benzofuroxan moieties are introduced per phenol. The most potent of the synthesized compounds exhibit high cytotoxicity against human duodenal adenocarcinoma (HuTu 80), human breast adenocarcinoma (MCF-7), and human cervical carcinoma cell lines. This toxicity is associated with the induction of apoptosis via the internal mitochondrial pathway and an increase in ROS production. Encouragingly, the index of selectivity relative to healthy tissues exceeds that for the reference drugs Doxorubicin and Sorafenib. The biostability of the leading compounds in whole mice blood is sufficiently high for their future quantification in biological matrices.
More Related Videos
Related Concept Videos
Directing and Steric Effects in Disubstituted Benzene Derivatives
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Frost Circles for Different Conjugated Systems
Hydrolysis of Chlorobenzene to Phenol: Dow Process
Combined Effects of Drugs: Synergism
Such synergistic combinations...
Electrophilic Aromatic Substitution: Sulfonation of Benzene

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
