Abstract:
1-(2-Aminoethylsulfonyl)-2-phosphorylpyrrolidines have been synthesized via boron trifluoride-catalyzed Arbuzov reaction of 2-ethoxy-1-(vinylsulfonyl)pyrrolidine with triethyl phosphite followed by aza-Michael reaction of thus obtained 2-phosphoryl-1-(vinylsulfonyl)pyrrolidine with secondary amines. The cytotoxicity of the prepared 1-(2-aminoethylsulfonyl)-2-phosphorylpyrrolidines against M-Hela tumor cell line is comparable with that of tamoxifen, whereas the cytotoxicity against normal cell line is twofold lower.
Citation:
R. Kh. Bagautdinova, L. I. Vagapova, A. V. Smolobochkin, A. S. Gazizov, A. R. Burilov, M. A. Pudovik, A. D. Voloshina, “Synthesis of 1-(2-aminoethylsulfonyl)-2-phosphorylpyrrolidines via consecutive Arbuzov and aza-Michael reactions and their antitumor activity”, Mendeleev Commun., 29:6 (2019), 686–687
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https://www.mathnet.ru/eng/mendc1631
https://www.mathnet.ru/eng/mendc/v29/i6/p686
This publication is cited in the following 5 articles:
Alexander Yu. Rulev, “Aza‐Michael Reaction: A Decade Later – Is the Research Over?”, Eur J Org Chem, 26:26 (2023)
A. Yu. Nikonov, I. V. Sterkhova, N. F. Lazareva, “2,2-Dimethyl-3-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1,3,2-benzoxazasilole: synthesis, properties, and structure”, Russ Chem Bull, 70:2 (2021), 386
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
Andrey V. Smolobochkin, Rakhymzhan A. Turmanov, Almir S. Gazizov, Alexandra D. Voloshina, Julia K. Voronina, Anastasiia S. Sapunova, Alexander R. Burilov, Michail A. Pudovik, “One-pot imination / Arbuzov reaction of 4-aminobutanal derivatives: Synthesis of 2-phosphorylpyrrolidines and evaluation of anticancer activity”, Tetrahedron, 76:33 (2020), 131369
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
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