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Enaminoketones - functional derivatives based on 7-hydroxy-3′,3′-dimethyl-3′H-spiro[chromen-2,1′-isobenzofuran]-8-carbaldehyde with aromatic amines. physicochemical studies and biological activity

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1. Title Title of document Enaminoketones - functional derivatives based on 7-hydroxy-3′,3′-dimethyl-3′H-spiro[chromen-2,1′-isobenzofuran]-8-carbaldehyde with aromatic amines. physicochemical studies and biological activity
2. Creator Author's name, affiliation, country X. T Nguyen; Southern Federal University;Institute of Chemistry, Vietnam Academy of Science and Technology
2. Creator Author's name, affiliation, country A. A Zantman; Southern Federal University
2. Creator Author's name, affiliation, country A. O Bulanov; Southern Federal University
2. Creator Author's name, affiliation, country T. T.T Nguyen; Institute for Tropical Technology, Vietnam Academy of Science and Technology
2. Creator Author's name, affiliation, country L. D Tran; Institute for Tropical Technology, Vietnam Academy of Science and Technology
2. Creator Author's name, affiliation, country H. D Vu; Hanoi University of Science and Technology
2. Creator Author's name, affiliation, country B. N Duong; Institute for Tropical Technology, Vietnam Academy of Science and Technology;Office of the State Council for Professorship, Ministry of Education and Training
2. Creator Author's name, affiliation, country V. A Lazarenko; National Research Center “Kurchatov Institute”
2. Creator Author's name, affiliation, country I. N Shcherbakov; Southern Federal University
3. Subject Discipline(s)
3. Subject Keyword(s) enaminoketones; spiropyrans; DFT calculations; anticancer activity
4. Description Abstract This research focuses on studying derivatives of 2-oxaindane spiropyran by its condensation with aromatic amines. The results showed that all the synthesized compounds are enaminoketones form in both solution and solid state. This is explained by the fact that during the formation of Schiff bases, the proton of the 7-hydroxyl group of the benzopyran part migrates to the azomethine nitrogen, which leads to the transition of the cyclic form of spiropyran into the corresponding enaminoketone. In the DMSO solution, the enaminoketones dynamic equilibrium of the E , Z -isomeric forms were observed. The structure of enaminoketone based on 3,4-dimethylaniline was proved by the X-ray diffraction method. The synthesized compounds were studied for their in vitro anticancer activity against human hepatocellular carcinoma (HepG2), breast carcinoma (MCF-7), lung cancer (A549), and carcinoma cells (KB). Enaminoketone with R = 3,4-СH3Ph is characterized by the highest activity, with IC50 values of 13.38 μM (KB). The results in vitro antioxidant activity test using 1,1-diphenyl-2-picrylhydrazyl (DPPH) indicated that enaminoketones were inactive.
5. Publisher Organizing agency, location ФИЦ КазНЦ РАН
6. Contributor Sponsor(s)
7. Date (DD-MM-YYYY) 15.05.2023
8. Type Status & genre Peer-reviewed Article
8. Type Type Research Article
9. Format File format
10. Identifier Uniform Resource Identifier https://journals.eco-vector.com/0044-460X/article/view/666987
10. Identifier Digital Object Identifier (DOI) 10.31857/S0044460X23050037
10. Identifier eLIBRARY Document Number (EDN) DBMYIR
11. Source Title; vol., no. (year) Žurnal obŝej himii; Vol 93, No 5 (2023)
12. Language English=en ru
13. Relation Supp. Files
14. Coverage Geo-spatial location, chronological period, research sample (gender, age, etc.)
15. Rights Copyright and permissions Copyright (c) 2023 Russian Academy of Sciences