Synthesis and evaluation of the anti-hepatitis B virus activity of 4′-Azido-thymidine analogs and 4′-Azido-2′-deoxy-5-methylcytidine analogs: structural insights for the development of a novel anti-HBV agent

Onitsuka, Kengo; Tokuda, Ryoh; Kuwata-Higashi, Nobuyo; Kumamoto, Hiroyuki; Aoki, Manabu; Amano, Masayuki; Kohgo, Satoru; Das, Debananda; Haraguchi, Kazuhiro; Mitsuya, Hiroaki; Imoto, Shuhei

doi:10.1080/15257770.2019.1664749

Cited by 2 publications

(2 citation statements)

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“…The introduction of a nitrogen atom into the heterocyclic fragment of uridine (1) and cytidine (3) at position 5 or 6 led to a sharp change in the antiviral activity. If 5-substituted 2'-deoxyuridines 9 and 10 are active against DNA viruses of herpes simplex and varicella zoster, then 6-azauridine (12), 5-azacytidine (13), and 2'-deoxy-5-azacytidine (decitabine) (14) (Fig. 2) already inhibit the replication of RNA viruses.…”

Section: Nucleoside Analogsmentioning

confidence: 99%

“…Figure 3 shows analogs of nucleosides 21-24, 26, 27 in which, in contrast to zidovudine (20), the azido group is located at the C-4' atom. These compounds became known for their high activity against hepatitis B (compounds 21-23, 26, 27) 13 or hepatitis C (compounds 24, 25) viruses. 3,14 It can be assumed that it is the introduction of the azido group at the С-4' position of 2'-deoxycytidine (6), 2'-deoxyadenosine (7), and 2'-deoxyguanosine (8) (Fig.…”

Section: Variation Of Substituents At the C-4' Atommentioning

confidence: 99%

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Antiviral nucleoside analogs

Катаев

Garifullin

2021

Chem Heterocycl Comp

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The minireview surveys the modification of native nucleosides as a result of which huge libraries of nucleoside analogs of various structures were synthesized. Particular attention is paid to the synthesis of the so-called prodrug forms of nucleoside analogs which ensure their penetration into the cell and metabolism to active 5'-triphosphate derivatives. All the best known antiviral cyclic nucleoside analogs approved for the treatment of HIV infections, hepatitis B, C, and influenza since the 1960s, as well as those in various stages of clinical trials in recent years, are listed. Nucleoside analogs that have shown the ability to inhibit the replication of SARS-CoV and MERS-CoV are discussed, including remdesivir, approved by the FDA for emergency use in the fight against COVID-19.

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Section: Nucleoside Analogsmentioning

confidence: 99%