Design, synthesis, and biological evaluation of new 2'-deoxy-2'-fluoro-4'-triazole cytidine nucleosides as potent antiviral agents. 2013

Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, PR China.

A series of 4'-[1,2,3]triazole-2'-deoxy-2'-fluoro-β-d-arabinofuranosylcytosines (9-17) were prepared by Cu(I)-mediated [3 + 2] cycloaddition reactions (CuAAC) of 1-(4'-azido-2'-deoxy-2'-fluoro-β-d-arabinofuranosyl)cytosine (1) with appropriate alkynes in good yields. Their structures were fully established by (1)H NMR, (13)C NMR, HRMS, and elemental analysis. Most of these nucleoside analogs exhibited potent anti-HIV-1 activity with no cytotoxicity observed at the highest tested concentration up to 25 μM. Among them, compounds 9, 10 and 13 exhibited extremely potent antiviral activity, thus had a great potential for further development as novel nucleoside reverse transcriptase inhibitors (NRTIs) for the treatment of HIV-1 infection. Besides, the anti-HBV activity of compounds 10, 11 and 17 had been investigated.

UI MeSH Term Description Entries
D008956 Models, Chemical Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment. Chemical Models,Chemical Model,Model, Chemical
D002470 Cell Survival The span of viability of a cell characterized by the capacity to perform certain functions such as metabolism, growth, reproduction, some form of responsiveness, and adaptability. Cell Viability,Cell Viabilities,Survival, Cell,Viabilities, Cell,Viability, Cell
D003562 Cytidine A pyrimidine nucleoside that is composed of the base CYTOSINE linked to the five-carbon sugar D-RIBOSE. Cytosine Ribonucleoside,Cytosine Riboside,Ribonucleoside, Cytosine,Riboside, Cytosine
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D004797 Enzyme-Linked Immunosorbent Assay An immunoassay utilizing an antibody labeled with an enzyme marker such as horseradish peroxidase. While either the enzyme or the antibody is bound to an immunosorbent substrate, they both retain their biologic activity; the change in enzyme activity as a result of the enzyme-antibody-antigen reaction is proportional to the concentration of the antigen and can be measured spectrophotometrically or with the naked eye. Many variations of the method have been developed. ELISA,Assay, Enzyme-Linked Immunosorbent,Assays, Enzyme-Linked Immunosorbent,Enzyme Linked Immunosorbent Assay,Enzyme-Linked Immunosorbent Assays,Immunosorbent Assay, Enzyme-Linked,Immunosorbent Assays, Enzyme-Linked
D006513 Hepatitis B e Antigens A closely related group of antigens found in the plasma only during the infective phase of hepatitis B or in virulent chronic hepatitis B, probably indicating active virus replication; there are three subtypes which may exist in a complex with immunoglobulins G. HBeAg,Hepatitis B e Antigen,Hepatitis Be Antigen,e Antigen,e Antigens,HBe Ag-1,HBe Ag-2,Hepatitis Be Antigens,Antigen, Hepatitis Be,Antigen, e,Antigens, Hepatitis Be,Antigens, e,Be Antigen, Hepatitis,Be Antigens, Hepatitis
D006514 Hepatitis B Surface Antigens Those hepatitis B antigens found on the surface of the Dane particle and on the 20 nm spherical and tubular particles. Several subspecificities of the surface antigen are known. These were formerly called the Australia antigen. Australia Antigen,HBsAg,Hepatitis B Surface Antigen,Antigen, Australia
D006515 Hepatitis B virus The type species of the genus ORTHOHEPADNAVIRUS which causes human HEPATITIS B and is also apparently a causal agent in human HEPATOCELLULAR CARCINOMA. The Dane particle is an intact hepatitis virion, named after its discoverer. Non-infectious spherical and tubular particles are also seen in the serum. Dane Particle,Hepatitis Virus, Homologous Serum,B virus, Hepatitis,Hepatitis B viruses,Particle, Dane,viruses, Hepatitis B
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral

Related Publications

Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
August 2015, European journal of medicinal chemistry,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
September 2011, European journal of medicinal chemistry,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
April 2022, Bioorganic & medicinal chemistry letters,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
July 2000, Bioorganic & medicinal chemistry,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
June 2009, European journal of medicinal chemistry,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
March 2020, Molecules (Basel, Switzerland),
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
June 1985, Journal of medicinal chemistry,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
November 2004, Archiv der Pharmazie,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
March 1999, Nucleosides & nucleotides,
Jie Wu, and Wenquan Yu, and Leixia Fu, and Wu He, and Yao Wang, and Baoshan Chai, and Chuanjun Song, and Junbiao Chang
March 1999, Bioorganic & medicinal chemistry,
Copied contents to your clipboard!