Sayapin Yurii A, Gusakov Eugeny A, Tupaeva Inna O, Dubonosov Alexander D, Dorogan Igor V, Tkachev Valery V, Goncharova Anna S, Shilov Gennady V, Kuznetsova Natalia S, Filippova Svetlana Y, Krasnikova Tatyana A, Boumber Yanis A, Maksimov Alexey Y, Aldoshin Sergey M, Minkin Vladimir I
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, Rostov-on-Don 344006, Russian Federation.
Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don 344090, Russian Federation.
Beilstein J Org Chem. 2025 Feb 17;21:358-368. doi: 10.3762/bjoc.21.26. eCollection 2025.
The acid-catalyzed reaction of benzo[()] derivatives of 2,3,3-trimethylindolenines with -chloranil leads to new 2-(benzo[()]indolin-2-yl)-5,6,7-trichloro-1,3-tropolones and 2-(benzo[()]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-3-benzo[]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 Hg ions in an acetonitrile solution. 2-(1,1-Dimethyl-1-benzo[]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone exhibited high in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines.
2,3,3-三甲基吲哚啉的苯并[()]衍生物与四氯对苯二醌的酸催化反应生成了新的2-(苯并[()]吲哚-2-基)-5,6,7-三氯-1,3-氧杂环庚三烯酮和2-(苯并[()]吲哚-2-基)-4,5,6,7-四氯-1,3-氧杂环庚三烯酮。基于PBE0/6-311+G(d,p)计算结果，确定了所得1,3-氧杂环庚三烯酮互变异构体的结构和能量特征。通过X射线衍射分析确定了2-(3,3-二甲基-3-苯并[]吲哚-2-基)-5,6,7-三氯-1,3-氧杂环庚三烯酮的结构。所得化合物在乙腈溶液中依次暴露于CN和Hg离子时，能够在420 - 440 nm和476 - 530 nm处切换发射。2-(1,1-二甲基-1-苯并[]吲哚-2-基)-5,6,7-三氯-1,3-氧杂环庚三烯酮对A431皮肤癌和H1299肺癌细胞系表现出高体外细胞毒性活性。
