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 C<sup>4</sup>-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship”, Mendeleev Commun., 2018, Volume 28, Issue 5,Pages <nobr>475

This article is cited in 7 papers

Communications

Novel bridged and caged C⁴-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship

N. A. Zefirov^ab, A. Kruth^c, B. Wobith^c, E. V. Nurieva^a, S. Riyaz^d, Ch. Venkata Ramana Reddy^d, S. A. Kuznetsov^c, O. N. Zefirova^ab

^a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^b 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
^c Institute of Biological Sciences, Cell Biology and Biosystems Technology, University of Rostock, Rostock, Germany
^d Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad, India

Abstract: New podophyllotoxin C⁴-derivatives with bridged and cage moieties were synthesized by the Steglich esterification of podophyllotoxin with polycyclic carboxylic acids or by etherication with (adamantan-1-yl)methanol in the presence of BF₃·Et₂O with the following separation of diastereomers. Most of the target compounds inhibited the growth of human lung carcinoma A549 cells, induced apoptosis, stimulated shortening of microtubules or induced their unusual curling and involution. The activity depends on the slightest differences in the structures of alicyclic moieties and the type of the bond between podophyllotoxin and alicyclic group.

Language: English

DOI: 10.1016/j.mencom.2018.09.007

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