Synthesis of biaryl-based carbazoles via C-H functionalization and exploration of their anticancer activities

• Published in: Organic & biomolecular chemistry 2024-11, Vol.22 (45), p.8916-8944
• Main Authors: Kaur, Ramandeep, Dilip, Haritha, Kirubakaran, Sivapriya, Babu, Srinivasarao Arulananda
• Format: Article
• Language: English
• Subjects: Anticancer properties; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Cancer; Carbazole; Carbazoles; Carbazoles - chemical synthesis; Carbazoles - chemistry; Carbazoles - pharmacology; Cell Line, Tumor; Cell Proliferation - drug effects; Cell Survival - drug effects; Cervical cancer; Chemical synthesis; Colon cancer; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HEK293 Cells; Humans; Lead compounds; Molecular Structure; Pharmaceutical sciences; Structure-Activity Relationship; Tumor cell lines
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d4ob01392a

The synthesis of a library of new biaryl-based carbazoles bidentate directing group-assisted C-H functionalization and preliminary screening of the anticancer properties of biaryl-based carbazoles is reported. While various classes of modified carbazoles are known for their applications in materials and medicinal chemistry, to our knowledge, the biological activities of designed biaryl-based carbazoles have been rarely known. Given the prominence of carbazoles in research in medicinal chemistry, we envisioned the scope for new scaffolds of carbazole-based biaryl structures. We screened the synthesized biaryl-based carbazoles for their anticancer properties against various cancer cell lines such as HeLa (cervical cancer), HCT116 (colon cancer), MDA-MB-231 and MDA-MB-468 (breast cancer). In addition, the hits were also tested in the human embryonic kidney cell line HEK293T to assess their impact on the viability of normal human cells in the presence of these compounds. In this preliminary study, we identified some of the biaryl-based carbazoles as lead compounds with anticancer activities.