Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

Irina Smirnova; Anastasiya Petrova; Gul’nara Giniyatullina; Anna Smirnova; Alexandrina Volobueva; Julia Pavlyukova; Vladimir Zarubaev; Tran Van Loc; Thao Tran Thi Phoung; Vu Thi Bich Hau; Nguyen Thi Thu Thuy; Myint Myint Khine; Oxana Kazakova

doi:10.3390/molecules27238499

Molecules (Dec 2022)

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

Irina Smirnova,
Anastasiya Petrova,
Gul’nara Giniyatullina,
Anna Smirnova,
Alexandrina Volobueva,
Julia Pavlyukova,
Vladimir Zarubaev,
Tran Van Loc,
Thao Tran Thi Phoung,
Vu Thi Bich Hau,
Nguyen Thi Thu Thuy,
Myint Myint Khine,
Oxana Kazakova

Affiliations

Irina Smirnova: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
Anastasiya Petrova: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
Gul’nara Giniyatullina: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
Anna Smirnova: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia
Alexandrina Volobueva: Department of Virology, St. Petersburg Pasteur Institute of Epidemiology and Microbiology, Experimental Virology Laboratory, 14 Mira St., St. Petersburg 197001, Russia
Julia Pavlyukova: St. Petersburg State Institute of Technology, 26 Moskovsky Av, St. Petersburg 190013, Russia
Vladimir Zarubaev: Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
Tran Van Loc: Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
Thao Tran Thi Phoung: Institute of Chemistry, Vietnamese Academy of Science and Technology, 18-Hoang Quoc Viet Street, Cau Giay District, Hanoi 1000, Vietnam
Vu Thi Bich Hau: National Institute of Hygiene and Epidemiology, 1 Yersin Street, Hai Ba Trung, Hanoi 10000, Vietnam
Nguyen Thi Thu Thuy: National Institute of Hygiene and Epidemiology, 1 Yersin Street, Hai Ba Trung, Hanoi 10000, Vietnam
Myint Myint Khine: Department of Chemistry, University of Yangon, University Avenue Road, Kamayut Township, Yangon 11041, Myanmar
Oxana Kazakova: Ufa Institute of Chemistry, The Ufa Federal Research Centre, The Russian Academy of Sciences, 71 Prospect Oktyabrya, Ufa 450054, Russia

DOI: https://doi.org/10.3390/molecules27238499
Journal volume & issue: Vol. 27, no. 23
p. 8499

Abstract

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A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50′s 67 and 107 μM) and -2 (IC50′s 86 and 68 μM correspondingly) serotypes.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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