Abstract:
Four new triterpenoids with alkyne moieties have been synthesized by the proposed procedure; among them, 3β,28-dihydroxy-29-norlup-20(30)-yne has demonstrated antiviral activity against papilloma virus and HCV replicon.
Citation:
O. B. Kazakova, N. I. Medvedeva, G. A. Tolstikov, O. S. Kukovinets, E. Yu. Yamansarov, L. V. Spirikhin, A. T. Gubaidullin, “Synthesis of terminal acetylenes using POCl3 in pyridine as applied to natural triterpenoids”, Mendeleev Commun., 20:4 (2010), 234–236
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This publication is cited in the following 17 articles:
Elmira F. Khusnutdinova, Anastasiya V. Petrova, Oxana B. Kazakova, “Antiviral potency of lupane and oleanane alkynyl-derivatives against human cytomegalovirus and papillomavirus”, J Antibiot, 77:1 (2024), 50
Zarema Galimova, Irina Smirnova, Alexander Lobov, Dmitriy Polovyanenko, Tatyana Rybalova, Oxana Kazakova, “One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid”, IJMS, 25:15 (2024), 8356
Lidia A. Baltina, Nataliia G. Komissarova, Studies in Natural Products Chemistry, 76, Studies in Natural Product Chemistry, 2023, 331
A. V. Petrova, ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference, 2390, ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference, 2022, 020058
O. B. Kazakova, I. E. Smirnova, ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference, 2390, ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference, 2022, 020028
Shaista Amin, M. Mumtaz Alam, Mymoona Akhter, A. K. Najmi, Nadeem Siddiqui, Asif Husain, M. Shaquiquzzaman, “A review on synthetic procedures and applications of phosphorus oxychloride (POCl3) in the last biennial period (2018–19)”, Phosphorus, Sulfur, and Silicon and the Related Elements, 196:3 (2021), 211
Elwira Chrobak, Maria Jastrzȩbska, Ewa Bȩbenek, Monika Kadela-Tomanek, Krzysztof Marciniec, Małgorzata Latocha, Roman Wrzalik, Joachim Kusz, Stanisław Boryczka, “Molecular Structure, In Vitro Anticancer Study and Molecular Docking of New Phosphate Derivatives of Betulin”, Molecules, 26:3 (2021), 737
Ekaterina E. Galenko, Firuza M. Shakirova, Vladimir A. Bodunov, Mikhail S. Novikov, Alexander F. Khlebnikov, “1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the synthesis of pyrrole-containing heterocycles”, Org. Biomol. Chem., 18:12 (2020), 2283
E. F. Khusnutdinova, G. N. Apryshko, A. V. Petrova, O. S. Kukovinets, O. B. Kazakova, “The Synthesis and Selective Cytotoxicity of New Mannich Bases, Derivatives of 19- and 28-Alkynyltriterpenoids”, Russ J Bioorg Chem, 44:1 (2018), 123
S.C. Jonnalagadda, P. Suman, D.C. Morgan, J.N. Seay, Studies in Natural Products Chemistry, 53, 2017, 45
E. V. Tret'yakova, E. V. Salimova, L. V. Parfenova, V. N. Odinokov, “Synthesis and modifications of alkyne derivatives of dihydroquinopimaric, maleopimaric, and fumaropimaric acids”, Russ J Org Chem, 52:10 (2016), 1496
Victoria V. Grishko, Natalia V. Galaiko, Irina A. Tolmacheva, Igor I. Kucherov, Vladimir F. Eremin, Eugene I. Boreko, Olga V. Savinova, Pavel A. Slepukhin, “Functionalization, cyclization and antiviral activity of A-secotriterpenoids”, European Journal of Medicinal Chemistry, 83 (2014), 601
E. F. Khusnutdinova, T. V. Lopatina, O. B. Kazakova, G. F. Akhmatshina, O. S. Kukovinets, “Synthesis and Cytotoxicity of Triterpene A-seco-Acid Propargylamides”, Chem Nat Compd, 50:5 (2014), 853
René Csuk, Christoph Nitsche, Ronny Sczepek, Stefan Schwarz, Bianka Siewert, “Synthesis of Antitumor‐Active Betulinic Acid‐Derived Hydroxypropargylamines by Copper‐Catalyzend Mannich Reactions”, Archiv der Pharmazie, 346:3 (2013), 232
O. B. Kazakova, N. I. Medvedeva, K. Yu. Suponitskii, “Synthesis and structure of an acetylene derivative of lupeol”, Chem Nat Compd, 47:3 (2011), 408
Oxana B. Kazakova, Natalya I. Medvedeva, Genrikh A. Tolstikov, Olga S. Kukovinets, Emil Y. Yamansarov, Leonid V. Spirikhin, Aidar T. Gubaidullin, “ChemInform Abstract: Synthesis of Terminal Acetylenes Using POCl3 in Pyridine as Applied to Natural Triterpenoids.”, ChemInform, 41:49 (2010)
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