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2-Methoxyestradiol and its analogs. Synthesis and structure—antiproliferative activity relationship

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Abstract

2-Methoxyestradiol is an estradiol metabolite capable of binding to the colchicine domain of the cell protein tubulin. The review systematizes the results of structure—activity studies on 2-methoxyestradiol analogs with various modifications of the A, B, and D rings and describes some synthetic approaches to such analogs. Ways of synthesis of metabolically stable 2-methoxyestradiol via modification of the 3- and 17-hydroxy groups, as well as by introduction of bulky substituents into the 17-position, are discussed. The design of 2-methoxyestradiol analogs lacking steroid fragment is also described.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119992, Russia

    N. A. Zefirov & O. N. Zefirova

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severnyi proezd 1, Chernogolovka, Moscow oblast, 142432, Russia

    O. N. Zefirova

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  1. N. A. Zefirov
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Correspondence to N. A. Zefirov.

Additional information

Original Russian Text © N.A. Zefirov, O.N. Zefirova, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 9, pp. 1231–1240.

On the Jubilee of Full Member of the Russian Academy of Sciences Nikolai Serafimovich Zefirov, a brilliant scientist in the fields of organic and medicinal chemistry, with wishes for further creative success

Nikolai Alekseevich Zefirov was born in 1992 in Moscow. In 2015 he graduated from the Faculty of Chemistry, Moscow State University. Author of 11 scientific publications. Since 2015 he works as laboratory assistant at the Faculty of Chemistry, Moscow State University.

Fields of interest: medicinal chemistry, computer-assisted molecular modeling, synthesis of adamantane and bicyclo[3.3.1]nonane derivatives, physiologically active substances.

Ol’ga Nikolaevna Zefirova was born in 1965 in Moscow. In 1987 she graduated from the Faculty of Chemistry, Moscow State University. Doctor of chemical sciences (specialization “Medicinal Chemistry”). Author of more than 150 publications, one monograph, and two patents (Russian Federation). Professor at the Faculty of Chemistry, Moscow State University.

Fields of interest: medicinal chemistry, tubulin ligands, cage and bridged fragments in the design of physiologically active compounds, structure—physiological activity relationships.

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Zefirov, N.A., Zefirova, O.N. 2-Methoxyestradiol and its analogs. Synthesis and structure—antiproliferative activity relationship. Russ J Org Chem 51, 1207–1216 (2015). https://doi.org/10.1134/S1070428015090018

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  • DOI: https://doi.org/10.1134/S1070428015090018

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