Abstract:
5-Hydroxymethyl-2-methoxyphenyl adamantane-1-acetate inhibits cell proliferation and stimulates depolymerization of microtubules of cancer cells to free tubulin. Its analogues were synthesized via the Steglich or Mitsunobu reactions to determine the role of structural subunits of the molecule in tubulin binding. Based on the structure–activity relationship studies, metabolically stable 1-[2-(5-hydroxymethyl-2-methoxyphenyl)ethyl]adamantane was invented, which exhibits a dual-target profile and retains in vitro activity observed for the lead compound.
Citation:
N. A. Zefirov, Yu. A. Evteeva, A. I. Krasnoperova, A. V. Mamaeva, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Tubulin targeted antimitotic agents based on adamantane lead compound: synthesis, SAR and molecular modeling”, Mendeleev Commun., 30:4 (2020), 421–423
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https://www.mathnet.ru/eng/mendc/v30/i4/p421
This publication is cited in the following 12 articles:
Aman Ragshaniya, Vijay Kumar, Ram Kumar Tittal, Kashmiri Lal, “Nascent pharmacological advancement in adamantane derivatives”, Archiv der Pharmazie, 357:3 (2024)
Aamal A. Al-Mutairi, Y. Shyma Mary, Y. Sheena Mary, Sreejit Soman, Hanan M. Hassan, Monirah A. Al-Alshaikh, Ali A. El-Emam, “Spectroscopic, Docking and MD Simulation Analysis of an Adamantane Derivative with Solvation Effects in Different Solvents”, Polycyclic Aromatic Compounds, 43:5 (2023), 4203
M. A. Dodokhova, I. M. Kotieva, A. V. Safronenko, S. V. Shlyk, N. V. Drobotya, D. B. Shpakovsky, “Microtubules as a target of antitumor drugs”, jour, 3:3 (2022), 25
Kirill S. Sadovnikov, Dmitry A. Vasilenko, Yulia A. Gracheva, Nikolay A. Zefirov, Eugene V. Radchenko, Vladimir A. Palyulin, Yuri K. Grishin, Vladislav A. Vasilichin, Alexander A. Shtil, Pavel N. Shevtsov, Elena F. Shevtsova, Tamara S. Kuznetsova, Sergei A. Kuznetsov, Alexander S. Bunev, Olga N. Zefirova, Elena R. Milaeva, Elena B. Averina, “Novel substituted 5‐methyl‐4‐acylaminoisoxazoles as antimitotic agents: Evaluation of selectivity to LNCaP cancer cells”, Archiv der Pharmazie, 355:5 (2022)
D. V. Danilov, V. S. D'yachenko, V. V. Burmistrov, G. M. Butov, I. A. Novakov, “Synthesis and properties of 1-[(3-fluoroadamantan-1-yl)methyl]-3-R-ureas and 1,1′-(alkan-1,n-diyl)bis{3-[(3-fluoroadamantan-1-yl)methyl]ureas} as promising soluble epoxide hydrolase inhibitors”, Russ Chem Bull, 71:1 (2022), 107
A. A. Alexeev, E. V. Nurieva, I. A. Elisseev, E. R. Milaeva, K. A. Lyssenko, O. N. Zefirova, “Bicyclic isothioureas for conjugation with tubulin targeted anticancer agents”, Mendeleev Commun., 32:6 (2022), 766–768
N. A. Zefirov, A. Glassl, E. V. Radchenko, A. N. Borovik, V. V. Stanishevskiy, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Podophyllotoxin esters with alicyclic residues: an insight into the origin of microtubule-curling effect in cancer cells”, Mendeleev Commun., 32:2 (2022), 173–175
N.A. Zefirov, A.V. Mamaeva, E.V. Radchenko, E.R. Milaeva, S.A. Kuznetsov, O.N. Zefirova, “Conjugate of podophyllotoxin with chlorambucil: synthesis, biological testing and molecular modeling”, BIOMED KHIM, 67:3 (2021), 289
Marat R. Baimuratov, Marina V. Leonova, Yuri N. Klimochkin, “Heterocycles Based on 1-((Z)-1,4-dibromobut-2-en-2-yl)adamantane”, Chem Heterocycl Comp, 57:3 (2021), 298
Anna V. Evdokimova, Alexander A. Alexeev, Evgeniya V. Nurieva, Elena R. Milaeva, Sergei A. Kuznetsov, Olga N. Zefirova, “N-(4-Methoxyphenyl)-substituted bicyclic isothioureas: effect on morphology of cancer cells”, Mendeleev Communications, 31:3 (2021), 288
N. A. Zefirov, A. V. Mamaeva, A. I. Krasnoperova, Yu. A. Evteeva, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Novel analogs of 5-hydroxymethyl-2-methoxyphenyl adamantane-1-acetate: synthesis, biotesting, and molecular modeling”, Russ Chem Bull, 70:3 (2021), 549
E. V. Nurieva, N. A. Zefirov, N. Fritsch, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Molecular design and synthesis of new heterobivalent compounds based on chlorambucil and colchicine”, Mendeleev Commun., 30:6 (2020), 706–708
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