Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2024-07-26 DOI:10.1007/s11172-024-4297-4

N. A. Zefirov, E. V. Khvatov, E. V. Nurieva, Ya. L. Esaulkova, A. S. Volobueva, V. V. Zarubaev, A. S. Goryashchenko, D. O. Yatsenko, V. I. Uvarova, D. I. Osolodkin, A. A. Ishmukhametov, O. N. Zefirova

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Abstract

Pyridine-containing amides of rimantadine (1-(1-adamantyl)ethylamine) were synthesized by the amidation of rimantadine hydrochloride by the corresponding acids in the NEt₃—N,N′-dicyclohexylcarbodiimide (DCC)—4-(N,N-dimethylamino)pyridine (DMAP) system as the analogues of previously described antiviral compounds 1-adamantylmethyl-5-aminoisoxazole-3-carboxylate and N-{[5-(thien-2-yl)isoxazol-3-yl]methyl}adamantane-1-amine. The spectrum of antiviral activity against the rimantadine-resistant A/PR/8/34 strain of influenza A virus, tick-borne encephalitis virus (TBEV) strain Absettarov (European subtype), yellow fever virus (YFV) vaccine strain 17D, and West Nile virus (WNV) strain Strix nebulosa-12 was studied. The structure—activity relationships were discussed. Synthesized compounds efficiently inhibited the reproduction of TBEV and WNV. N-[1-(Adamantan-1-yl)ethyl]picolinamide efficiently inhibited the reproduction of enveloped viruses with both type I (influenza) and type II (flaviviruses) fusion proteins. The antiviral activity against the rimantadine-resistant influenza virus A/PR/8/34 and a low cytotoxicity (high selectivity index) were revealed for N-[1-(adamantan-1-yl)ethyl]-isonicotinamide.

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对黄病毒和抗金刚烷胺甲型流感病毒株具有抗病毒活性的金刚烷胺衍生物

在 NEt3-N,N′-二环己基碳二亚胺（DCC）-4-（N、N,N′-二环己基碳二亚胺（DCC）-4-(N,N-二甲基氨基)吡啶（DMAP）体系中的相应酸作为先前描述的抗病毒化合物 1-金刚烷甲基-5-氨基异恶唑-3-羧酸盐和 N-{[5-(噻吩-2-基)异恶唑-3-基]甲基}金刚烷-1-胺的类似物。研究了它们对抗耐利曼他定的甲型流感病毒 A/PR/8/34 株、蜱传脑炎病毒（TBEV）Absettarov 株（欧洲亚型）、黄热病病毒（YFV）疫苗株 17D 和西尼罗河病毒（WNV）株 Strix nebulosa-12 的抗病毒活性谱。讨论了结构-活性关系。合成的化合物能有效抑制 TBEV 和 WNV 的繁殖。N-[1-(金刚烷-1-基)乙基]吡啶酰胺能有效抑制具有 I 型（流感）和 II 型（黄病毒）融合蛋白的包膜病毒的繁殖。结果表明，N-[1-（金刚烷-1-基）乙基]异烟酰胺对抗金刚烷胺流感病毒 A/PR/8/34 具有抗病毒活性，且细胞毒性低（选择性指数高）。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.