E. V. Nurieva, N. A. Zefirov, A. V. Mamaeva, Yu. K. Grishin, S. A. Kuznetsov, O. N. Zefirova, “Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif”, Mendeleev Commun., 2017, Volume 27, Issue 3,Pages <nobr>240

This article is cited in 6 papers

Communications

Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif

E. V. Nurieva^a, N. A. Zefirov^a, A. V. Mamaeva^a, Yu. K. Grishin^a, S. A. Kuznetsov^b, O. N. Zefirova^ac

^a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^b Institute of Biological Sciences, Cell Biology and Biosystems Technology, University of Rostock, Rostock, Germany
^c Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

Abstract: Two pairs of bicyclo[3.3.1]nonane derivatives with 2-methoxyphenol moiety were synthesized as non-steroidal 2-methoxyestradiol mimetics demonstrating noticeable cytotoxicity to human lung carcinoma cell line A549. Compounds with 2-methoxyphenol annulated with bicyclo[3.3.1]nonane fragment were obtained using BF₃-assisted oxirane opening in 5-(4-benzyloxy-3-methoxyphenyl)-1-oxaspiro[2.5]octanes with simultaneous intramolecular cyclization and reduction as the key step. endo-7-Hydroxybicyclo[3.3.1]nonane-exo-3-carboxylic acid was converted into two esters containing 2-methoxyphenol fragment in either acid or alcohol part of the molecule.

Language: English

DOI: 10.1016/j.mencom.2017.05.007

	*Supplementary materials:*
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