Tricyclic 2′-C-Modified Nucleosides as Potential Anti-HCV Therapeutics

被引：19

作者：

Wauchope, Orrette R. ^{[2
]}

Tomney, Matthew J. ^{[2
]}

Pepper, Joseph L. ^{[2
]}

Korba, Brent E. ^{[1
]}

Seley-Radtke, Katherine L. ^{[1
]}

机构：

[1] Georgetown Univ, Med Ctr, Dept Microbiol & Immunol, Washington, DC 20057 USA

[2] Univ Maryland, Dept Chem & Biochem, Baltimore, MD 21250 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 20期

关键词：

C VIRUS-REPLICATION; INHIBITORS; DESIGN;

D O I：

10.1021/ol101482h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Promising biological activity in a number of therapeutic areas has been reported for both tricyclic nucleosides and 2'-modified nucleosides. In particular, disubstitution at the C-2' position of nucleosides has resulted in significant activity against the hepatitis C virus (HCV). Combining this with the observation that tricyclic nucleosides developed in our laboratory have been shown to inhibit the RNA-dependent RNA polymerase NS5B led to the design of a series of 2'-modified tricyclic nucleosides. Details of the synthesis, structural characterization, and preliminary biological results are reported.

引用

页码：4466 / 4469

页数：4

共 41 条

[21] siRNA Modified with 2-Deoxy-2-C-methylpyrimidine Nucleosides [J].

Dellafiore, Maria ;

Avino, Anna ;

Alagia, Adele ;

Montserrat, Javier M. ;

Iribarren, Adolfo M. ;

Eritja, Ramon .

CHEMBIOCHEM, 2018, 19 (13) :1409-1413

[22] Chitosan and its derivatives as polymeric anti-viral therapeutics and potential anti-SARS-CoV-2 nanomedicine [J].

Tan, Rebecca Shu Ling ;

Hassandarvish, Pouya ;

Chee, Chin Fei ;

Chan, Lai Wah ;

Wong, Tin Wui .

CARBOHYDRATE POLYMERS, 2022, 290

[23] Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors [J].

Ding, YL ;

An, HY ;

Hong, Z ;

Girardet, JL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :725-727

[24] Synthesis and Anti-HCV Activities of 4′-Fluoro-2′-Substituted Uridine Triphosphates and Nucleotide Prodrugs: Discovery of 4′-Fluoro-2′-C-methyluridine 5′-Phosphoramidate Prodrug (AL-335) for the Treatment of Hepatitis C Infection [J].

Wang, Guangyi ;

Dyatkina, Natalia ;

Prhavc, Marija ;

Williams, Caroline ;

Serebryany, Vladimir ;

Hu, Yujian ;

Huang, Yongfei ;

Wan, Jinqiao ;

Wu, Xiangyang ;

Deval, Jerome ;

Fung, Amy ;

Jin, Zhinan ;

Fan, Hua ;

Shaw, Kenneth ;

Kang, Hyunsoon ;

Zhang, Qingling ;

Tam, Yuen ;

Stoycheva, Antitsa ;

Jekle, Andreas ;

Smith, David B. ;

Beigelman, Leonid .

JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (09) :4555-4570

[25] Computational Screening of Neuropilin-1 Unveils Novel Potential Anti-SARS-CoV-2 Therapeutics [J].

Afiadenyo, Michael ;

Adams, Latif ;

Agoni, Clement ;

Moane, Siobhan ;

Mckeon-Bennett, Michelle ;

Obiri-Yeboah, Dorcas ;

Singh, Jasdeep .

CHEMISTRY & BIODIVERSITY, 2023, 20 (12)

[26] Syntheses of nucleosides with 2′-spirolactam and 2′-spiropyrrolidine moieties as potential inhibitors of hepatitis C virus NS5B polymerase [J].

Dang, Qun ;

Zhang, Zhibo ;

Tang, Bingyu ;

Song, Yang ;

Wu, Ling ;

Chen, Tongqian ;

Bogen, Stephane ;

Girijavallabhan, Vinay ;

Olsen, David B. ;

Meinke, Peter T. .

TETRAHEDRON LETTERS, 2014, 55 (28) :3813-3816

[27] Discovery of a 2′-α-Fluoro-2′-β-C-(fluoromethyl) Purine Nucleotide Prodrug as a Potential Oral Anti-SARS-CoV-2 Agent [J].

Liang, Lan ;

Meng, Yonggang ;

Chang, Xiaoyu ;

Li, Ertong ;

Huang, Yucen ;

Yan, Liming ;

Lou, Zhiyong ;

Peng, Youmei ;

Zhu, Bo ;

Yu, Wenquan ;

Chang, Junbiao .

JOURNAL OF MEDICINAL CHEMISTRY, 2025, 68 (02) :1994-2007

[28] Syntheses of nucleosides with a 1′,2′-β-lactam moiety as potential inhibitors of hepatitis C virus NS5B polymerase [J].

Dang, Qun ;

Zhang, Zhibo ;

Bai, Yunfeng ;

Sun, Ruijun ;

Yin, Jie ;

Chen, Tongqian ;

Bogen, Stephane ;

Girijavallabhan, Vinay ;

Olsen, David B. ;

Meinke, Peter T. .

TETRAHEDRON LETTERS, 2014, 55 (40) :5576-5579

[29] Synthesis and anti-HCV activity of novel 5-arylmethylene-1,3-thiazolidi-n-4-one derivatives via suppression of NS5B polymerase and COX-2 [J].

Kulabas, Necla ;

Lee, Jin-Ching ;

Ozakpinar, Ozlem Bingol ;

Kucukguzel, Ilkay .

JOURNAL OF MOLECULAR STRUCTURE, 2024, 1311

[30] Synthesis and biological evaluation of novel anti-hepatitis C virus (HCV) agents: 2-hydroxylphenethyl sulfanyl-oxopyrimidines [J].

Wu, Daochun ;

Feng, Yue ;

Wang, Hua ;

Yang, Junfeng ;

Chen, Xian ;

Wang, Yueping ;

Lai, Christopher Cong ;

Zhang, Yufang ;

Li, Cong ;

Xia, Xueshan ;

He, Yanping .

MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (07) :1388-1396

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