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.
Citation:
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., 27:3 (2017), 240–242
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https://www.mathnet.ru/eng/mendc1954
https://www.mathnet.ru/eng/mendc/v27/i3/p240
This publication is cited in the following 6 articles:
Enrika Celitan, Albinas Zilinskas, Jolanta Sereikaite, “Screening of some vegetables for the biotransformation of bicyclo[3.3.1]nonane-2,6-diol diacetate”, Green Chemistry Letters and Reviews, 15:1 (2022), 45
Kseniya N. Sedenkova, Olga V. Ryzhikova, Svetlana A. Stepanova, Alexei D. Averin, Sergei V. Kositov, Yuri K. Grishin, Igor P. Gloriozov, Elena B. Averina, “Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3”, Molecules, 27:20 (2022), 6889
N. S. Baleeva, V. B. Rybakov, E. A. Ivleva, V. A. Shiryaev, Yu. N. Klimochkin, “Synthesis and Chemical Transformations of 7-Hydroxybicyclo[3.3.1]nonane-3-carbohydrazide”, Russ J Org Chem, 56:11 (2020), 1942
E. A. Lavrushkina, V. M. Shibilev, N. A. Zefirov, E. F. Shevtsova, P. N. Shevtsov, S. A. Kuznetsov, O. N. Zefirova, ““Triple” mutual prodrug based on 2-methoxyestradiol: synthesis and biotesting in vitro”, Russ Chem Bull, 69:3 (2020), 558
E. V. Nurieva, N. A. Zefirov, A. V. Mamaeva, B. Wobith, S. A. Kuznetsov, O. N. Zefirova, “Synthesis of steroid analogs of tubuloclustin, their cytotoxicity and effect on microtubules of A549 carcinoma cells”, Russ Chem Bull, 67:4 (2018), 688
N. A. Zefirov, A. Kruth, B. Wobith, E. V. Nurieva, S. Riyaz, Ch. Venkata Ramana Reddy, S. A. Kuznetsov, O. N. Zefirova, “Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship”, Mendeleev Commun., 28:5 (2018), 475–478
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