Brønsted acid- and Ni(ii)-catalyzed C-H oxidation/rearrangement of cyclotriveratrylenes (CTVs) to cyclic and acyclic quinones as potential anti-cancer agents
| Title | Brønsted acid- and Ni(ii)-catalyzed C-H oxidation/rearrangement of cyclotriveratrylenes (CTVs) to cyclic and acyclic quinones as potential anti-cancer agents |
| Publication Type | Journal Article |
| Year of Publication | 2024 |
| Authors | Darole, RS, Choudhary, SSingh, Sharma, H, Mali, BP, Gopu, B, Vanka, K, Senthilkumar, B |
| Journal | Organic and biomolecular chemistry |
| Volume | 22 |
| Issue | 5 |
| Pagination | 1038-1046 |
| Date Published | JAN |
| Type of Article | Article |
| ISSN | 1477-0520 |
| Abstract | This paper describes a simple and practical protocol for the direct synthesis of acyclic and cyclic quinone derivatives via an acid-promoted nickel(ii)-catalyzed inner rim C-H oxidation of cyclotriveratrylene (CTV) and its analogues. The cyclic quinone derivatives resulted from trimethoxy-cyclotriveratrylene (TCTV) through C-C bond formation via intramolecular ipso substitution followed by subsequent anionic rearrangement containing stereo-vicinal quaternary centers. The DFT calculations strongly support the experimental findings and reveal the role of Bronsted acids in the C-H bond activation of CTV. All the newly synthesized compounds were screened for their in vitro anti-cancer activity using colorimetric SRB assay analysis. Among them, compounds 3a, 3d, 3h, 4a, 4b, 4c and 4e exhibited moderate anticancer activity against A549, HCT-116, PC-3, MDA-MB-231, HEK-293 and SW620 human cancer cell lines. |
| DOI | 10.1039/d3ob01428b |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.2 |