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

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

Ol'ga Nikolaevna Zefirova 1
Ol'ga Nikolaevna Zefirova
, 
Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Heiko Lemcke 2
Heiko Lemcke
, 
Andrey Andreevich Ivanov 3
Andrey Andreevich Ivanov
, 
Nikolai Vasil'evich Zyk 1
Nikolai Vasil'evich Zyk
, 
Dieter G Weiss 2
Dieter G Weiss
, 
Sergei A Kuznetsov 2
Sergei A Kuznetsov
, 
Nikolai Serafimovich Zefirov 1
Nikolai Serafimovich Zefirov
10.1016/j.mencom.2008.07.003
Published 2008-07-17
Communication , Volume 18, Issue 4, 183-185
22
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Zefirova O. N. et al. Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives // Mendeleev Communications. 2008. Vol. 18. No. 4. pp. 183-185.
GOST all authors (up to 50) Copy
Zefirova O. N., Nurieva E. V., Lemcke H., Ivanov A. A., Zyk N. V., Weiss D. G., Kuznetsov S. A., Zefirov N. S. Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives // Mendeleev Communications. 2008. Vol. 18. No. 4. pp. 183-185.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2008.07.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.07.003
TI - Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives
T2 - Mendeleev Communications
AU - Zefirova, Ol'ga Nikolaevna
AU - Nurieva, Evgeniya Vladimirovna
AU - Lemcke, Heiko
AU - Ivanov, Andrey Andreevich
AU - Zyk, Nikolai Vasil'evich
AU - Weiss, Dieter G
AU - Kuznetsov, Sergei A
AU - Zefirov, Nikolai Serafimovich
PY - 2008
DA - 2008/07/17
PB - Mendeleev Communications
SP - 183-185
IS - 4
VL - 18
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2008_Zefirova,
author = {Ol'ga Nikolaevna Zefirova and Evgeniya Vladimirovna Nurieva and Heiko Lemcke and Andrey Andreevich Ivanov and Nikolai Vasil'evich Zyk and Dieter G Weiss and Sergei A Kuznetsov and Nikolai Serafimovich Zefirov},
title = {Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives},
journal = {Mendeleev Communications},
year = {2008},
volume = {18},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.07.003},
number = {4},
pages = {183--185},
doi = {10.1016/j.mencom.2008.07.003}
}
MLA
Cite this
MLA Copy
Zefirova, Ol'ga Nikolaevna, et al. “Design, synthesis and bioactivity of simplified taxol analogues on the basis of bicyclo[3.3.1]nonane derivatives.” Mendeleev Communications, vol. 18, no. 4, Jul. 2008, pp. 183-185. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.07.003.

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.

References

1.
Taxol, a molecule for all seasons
Kingston D.G.
Chemical Communications, 2001
2.
10.1016/j.mencom.2008.07.003_bib2
Zefirova
Zh. Org. Khim., 2005
3.
Synthesis of Extremely Simplified Compounds Possessing the Key Pharmacophore Units of Taxol, Phenylisoserine and Oxetane Moieties.
FUJI K., WATANABE Y., OHTSUBO T., NURUZZAMAN M., HAMAJIMA Y., KOHNO M.
Chemical and Pharmaceutical Bulletin, 2011
4.
New synthetic inhibitors of microtubule depolymerization.
Klar U., Graf H., Schenk O., Röhr B., Schulz H.
Bioorganic and Medicinal Chemistry Letters, 1998
5.
Design and synthesis of de novo cytotoxic alkaloids through mimicking taxoid skeleton
Geng X., Geney R., Pera P., Bernacki R.J., Ojima I.
Bioorganic and Medicinal Chemistry Letters, 2004
6.
Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)
Almqvist F., Manner S., Thornqvist V., Berg U., Wallin M., Frejd T.
Organic and Biomolecular Chemistry, 2004
7.
Design, synthesis, and bioactivity of simplified paclitaxel analogs based on the T-Taxol bioactive conformation
Ganesh T., Norris A., Sharma S., Bane S., Alcaraz A.A., Snyder J.P., Kingston D.G.
Bioorganic and Medicinal Chemistry, 2006
9.
10.1016/j.mencom.2008.07.003_bib9
Zefirova
Zh. Org. Khim., 2002
10.
10.1016/j.mencom.2008.07.003_bib10
Averina
Vestnik Mosk. Univ. 2. Khim., 2002
11.
Macromodel—an integrated software system for modeling organic and bioorganic molecules using molecular mechanics
Mohamadi F., Richards N.G., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C.
Journal of Computational Chemistry, 1990
12.
The binding conformation of Taxol in β-tubulin: A model based on electron crystallographic density
Snyder J.P., Nettles J.H., Cornett B., Downing K.H., Nogales E.
Proceedings of the National Academy of Sciences of the United States of America, 2001
14.
10.1016/j.mencom.2008.07.003_bib14
Momose
Chem. Pharm. Bull., 1978
16.
Zefirova O.N., Nurieva E.V., Nuriev V.N., Potekhin K.A., Maleev A.V., Zyk N.V., Zefirov N.S.
Mendeleev Communications, 2007
17.
Proximity Effects. XLIII. The Solvolysis of 4-Cyclooctene-1-methyl Brosylate1,2
Cope A.C., Nealy D.L., Scheiner P., Wood G.
Journal of the American Chemical Society, 1965
18.
Synthesis of 7-carboxytricyclo[3.3.1.03,7]nonan-3-ol
Renzoni G.E., Borden W.T.
Journal of Organic Chemistry, 1983
19.
10.1016/j.mencom.2008.07.003_bib19
Partch
Croat. Chem. Acta, 1985
20.
10.1016/j.mencom.2008.07.003_bib20
Kiryukhin
Vestnik Mosk. Univ. 2. Khim., 2007
22.
High molecular weight protein MAP 2 promoting microtubuleassembly in vitro is associated with microtubules in cells
KUZNETSOV S., RODIONOV V., BERSHADSKY A., GELFAND V., ROSENBLAT V.
Cell Biology International Reports, 1980
23.
D. G. Weiss, in Cell Biology: A Laboratory Handbook, ed. J. E. Celis, Academic Press, San Diego, 2005, vol. 3, p. 57.
24.
Microtubule-associated proteins and microtubule-based translocators have different binding sites on tubulin molecule.
Rodionov V.I., Gyoeva F.K., Kashina A.S., Kuznetsov S.A., Gelfand V.I.
Journal of Biological Chemistry, 1990