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Mendeleev Communications, 2008, Volume 18, Issue 4, Pages 183–185
DOI: https://doi.org/10.1016/j.mencom.2008.07.003
(Mi mendc3289)
 

This article is cited in 22 scientific papers (total in 22 papers)

Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives

O. N. Zefirovaa, E. V. Nurievaa, H. Lemckeb, A. A. Ivanovc, N. V. Zyka, D. G. Weissb, S. A. Kuznetsovb, N. S. Zefirova

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: Four specially designed bicyclo[3.3.1]nonane-based structures were synthesised and found to be cytotoxic at micromolar concentrations and to cause slight non-specific tubulin aggregation.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (82.1 Kb)


Citation: O. N. Zefirova, E. V. Nurieva, H. Lemcke, A. A. Ivanov, N. V. Zyk, D. G. Weiss, S. A. Kuznetsov, N. S. Zefirov, “Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives”, Mendeleev Commun., 18:4 (2008), 183–185
Linking options:
  • https://www.mathnet.ru/eng/mendc3289
  • https://www.mathnet.ru/eng/mendc/v18/i4/p183
  • This publication is cited in the following 22 articles:
    1. Vadim A. Shiryaev, Irina V. Sokolova, Anastasiya M. Gorbachova, Victor B. Rybakov, Andrey K. Shiryaev, Yuri N. Klimochkin, “Convenient synthesis of endo,endo- and endo,exo-bicyclo[3.3.1]nonane diamines”, Tetrahedron, 117-118 (2022), 132828  crossref
    2. 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  crossref
    3. 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  crossref
    4. Marco Cianfanelli, Giorgio Olivo, Michela Milan, Robertus J. M. Klein Gebbink, Xavi Ribas, Massimo Bietti, Miquel Costas, “Enantioselective C–H Lactonization of Unactivated Methylenes Directed by Carboxylic Acids”, J. Am. Chem. Soc., 142:3 (2020), 1584  crossref
    5. Dmitry A. Vasilenko, Evgenia V. Dueva, Liubov I. Kozlovskaya, Nikolay A. Zefirov, Yuri K. Grishin, Gennady M. Butov, Vladimir A. Palyulin, Tamara S. Kuznetsova, Galina G. Karganova, Olga N. Zefirova, Dmitry I. Osolodkin, Elena B. Averina, “Tick-borne flavivirus reproduction inhibitors based on isoxazole core linked with adamantane”, Bioorganic Chemistry, 87 (2019), 629  crossref
    6. 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  mathnet  crossref
    7. Olga N. Zefirova, Evgeniya V. Nurieva, Birgit Wobith, Vladimir V. Gogol, Nikolay A. Zefirov, Andrei V. Ogonkov, Dmitrii V. Shishov, Nikolay S. Zefirov, Sergei A. Kuznetsov, “Novel antimitotic agents related to tubuloclustin: synthesis and biological evaluation”, Mol Divers, 21:3 (2017), 547  crossref
    8. N. A. Zefirov, E. V. Nurieva, Yu. A. Pikulina, A. V. Ogon´kov, B. Wobith, S. A. Kuznetsov, O. N. Zefirova, “Adamantane acid esters with alkoxyaryl alcohols: Synthesis, antiproliferative activity, and influence on microtubule network of tumor cells”, Russ Chem Bull, 66:8 (2017), 1503  crossref
    9. D. A. Vasilenko, E. B. Averina, N. A. Zefirov, B. Wobith, Yu. K. Grishin, V. B. Rybakov, O. N. Zefirova, T. S. Kuznetsova, S. A. Kuznetsov, N. S. Zefirov, “Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties”, Mendeleev Commun., 27:3 (2017), 228–230  mathnet  crossref
    10. 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  mathnet  crossref
    11. James A. Bull, Rosemary A. Croft, Owen A. Davis, Robert Doran, Kate F. Morgan, “Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry”, Chem. Rev., 116:19 (2016), 12150  crossref
    12. Guan Wen, Xiao-Xia Qu, Dan Wang, Xing-Xiu Chen, Xin-Chuan Tian, Feng Gao, Xian-Li Zhou, “Recent advances in design, synthesis and bioactivity of paclitaxel-mimics”, Fitoterapia, 110 (2016), 26  crossref
    13. E. V. Nurieva, N. A. Zefirov, N. S. Zefirov, S. A. Kuznetsov, O. N. Zefirova, “Synthesis and antiproliferative activity of combretastatin derivatives with adamantane fragment”, Russ Chem Bull, 64:9 (2015), 2248  crossref
    14. N. A. Zefirov, Ya. S. Glazkova, I. V. Kuznetsova, E. V. Nurieva, O. N. Zefirova, “Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane”, Moscow Univ. Chem. Bull., 70:2 (2015), 69  crossref
    15. O. N. Zefirova, E. V. Nurieva, Ya. S. Glazkova, N. A. Zefirov, A. V. Mamaeva, B. Wobith, V. I. Romanenko, N. A. Lesnaya, E. M. Treshchalina, S. A. Kuznetsov, “Antiproliferative Activity of Tubuloclustin and its Steroid Analogs”, Pharm Chem J, 48:6 (2014), 373  crossref
    16. Kunal Nepali, Sahil Sharma, Manmohan Sharma, P.M.S. Bedi, K.L. Dhar, “Rational approaches, design strategies, structure activity relationship and mechanistic insights for anticancer hybrids”, European Journal of Medicinal Chemistry, 77 (2014), 422  crossref
    17. David G. I. Kingston, James P. Snyder, “The Quest for a Simple Bioactive Analog of Paclitaxel as a Potential Anticancer Agent”, Acc. Chem. Res., 47:8 (2014), 2682  crossref
    18. D. V. Shishov, E. V. Nurieva, N. S. Zefirov, A. V. Mamaeva, O. N. Zefirova, “Synthesis of 5-hydroxy-4-methoxytricyclo[7.3.1.02,7]trideca-2,4,6-trien- 8-one – precursor of putative bioisosteric colchicine analogues”, Mendeleev Commun., 24:6 (2014), 370–371  mathnet  crossref
    19. O. N. Zefirova, N. S. Zefirov, “Targeted application of bridged fragments in the design of physiologically active compounds”, Russ Chem Bull, 62:2 (2013), 325  crossref
    20. Claire Le Manach, Aurélie Baron, Régis Guillot, Boris Vauzeilles, Jean-Marie Beau, “Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures”, Tetrahedron Letters, 52:13 (2011), 1462  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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