Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones
Year: 2025
Type: article
Abstract: The acid-catalyzed reaction of benzo[e(g)] derivatives of 2,3,3-trimethylindolines with o-chloranil leads to the new 2-(benzo[e(g)]indolin-2-yl)-5,6,7-trichloro-1,3-tropolones and 2-(benzo[e(g)]indolin-2-yl)-4,5,6,7-tetrachloro-1,3-tropolones. Based on the results of PBE0/6-311+G(d,p) calculations, the structural and energetic characteristics of the tautomeric forms of the obtained 1,3-tropolones were determined. The structure of 2-(3,3-dimethyl-3H-benzo[g]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone was determined by X-ray diffraction analysis. The compounds obtained are capable of switching emission at 420-440 nm and 476–530 nm upon successive exposure to CN- and Hg2+ ions in an acetonitrile solution. 2-(1,1-Dimethyl-1H-benzo[e]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone exhibited high cytotoxic activity in vitro against A431 skin cancer and H1299 lung cancer cell lines.
DOI: 10.3762/bjoc.21.26
Authors: Yurii A. Sayapin, Eugeny A. Gusakov, Inna O. Tupaeva, Alexander D. Dubonosov, Igor V. Dorogan, Valerii V. Tkachev, Anna S. Goncharova, Gennadii V. Shilov, Natalia S. Kuznetsova, Svetlana Y. Filippova, Tatyana A. Krasnikova, Yanis A. Boumber, Alexey Y. Maksimov, Sergey M. Aldoshin, Vladimir I. Minkin
Institutions: Russian Academy of Sciences, Southern Scientific Center, Southern Federal University, Institute of Problems of Chemical Physics, Rostov Research Institute of Oncology, Kazan Federal University, University of Alabama at Birmingham, O'Neal Comprehensive Cancer Center, Lomonosov Moscow State University
Language: English
Subfield: Spectroscopy
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4407665778