Abstract:
The Friedel–Crafts-type reaction of 5-allyl-2,3,5-trichlorocyclopent-2-enones with mono-, di- and trimethoxybenzenes affords the arene ketovinylation products with the cleavage of C3–Cl bond in the starting trichlorocyclopentenones. The cytotoxocity of the products toward normal HEK293 cell lines and three cancer cell lines, SH-SY5Y, A549 and MCF-7, was evaluated.
Citation:
V. A. Egorov, F. A. Gimalova, Z. R. Zileeva, L. F. Zainullina, Yu. V. Vakhitova, M. S. Miftakhov, “2,3,5-Trichlorocyclopent-2-enone derivatives in the Friedel–Crafts reaction with methoxybenzenes and the anticancer activity of the products”, Mendeleev Commun., 29:2 (2019), 174–175
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https://www.mathnet.ru/eng/mendc1461
https://www.mathnet.ru/eng/mendc/v29/i2/p174
This publication is cited in the following 9 articles:
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov, “Synthesis of (Carboxymethylidene)cyclopentenedione Derivatives via the Oxidative Cleavage of the Allylic Double Bond in 2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione”, Russ J Org Chem, 60:11 (2024), 2298
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov, “Double Acylation Product in the SnCl4-promoted Reaction of 4,5-Dichlorocyclopent-4-en-1,3-dione with 1,3,5-Trimethoxybenzene”, Russ J Org Chem, 59:8 (2023), 1449
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov, “Double acylation product in the snsl<sub>4</sub>-promoted reaction of 4,5-dichlorocyclopent-4-en-1,3-dione with 1,3,5-trimethoxybenzene”, Žurnal organičeskoj himii, 59:8 (2023), 1096
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, D. V. Ishmetova, M. S. Miftakhov, “Zinc-promoted Reactions of (2Z,E)-[2-Aryl(hetaryl)methylidene]-4-chloro-5-phenyl(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-diones with Methyl Bromoacetate”, Russ J Org Chem, 58:11 (2022), 1668
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, A. N. Lobov, D. V. Ishmetova, V. A. Vakhitov, M. S. Miftakhov, “Cytotoxicity of novel cross-conjugated arylated cyclopentene-1,3-diones”, Mendeleev Commun., 32:2 (2022), 183–185
V. A. Egorov, L. M. Khalilov, E. S. Mescheryakova, F. A. Gimalova, M. S. Miftakhov, “2,4-Dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione derivatives in the reaction with CrCl2”, Russ Chem Bull, 70:1 (2021), 128
Alexander S. Bunev, Dmitry A. Khochenkov, Yulia A. Khochenkova, Yulia S. Machkova, Elena V. Varakina, Rovshan E. Gasanov, Marina A. Troshina, Olga S. Avdyakova, “Synthesis and anticancer activity of novel 2-alkylthio-4-amino-5-(thiazol-2-YL)pyrimidines”, Synthetic Communications, 51:16 (2021), 2521
D. A. Khochenkov, Yu. A. Khochenkova, Yu. S. Machkova, R. E. Gasanov, E. V. Stepanova, A. S. Bunev, “Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines”, Mendeleev Commun., 30:5 (2020), 604–606
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov, “New Differently Functionalized Cyclopentenediones”, Russ J Org Chem, 55:12 (2019), 1869
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