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Synthesis and Antiviral Activity of Novel Nucleosides

Author: TaoLe
Tutor: ChangJunBiao
School: Henan University
Course: Organic Chemistry
Keywords: Antivirus D-xylose Nucleoside Synthesis
CLC: TQ464
Type: Master's thesis
Year: 2007
Downloads: 162
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Abstract


There are about a hundred and seventy million HCV carriers in the world. In the United States, 2%～3% of people carry the hepatitis C virus, 30% of HCV carriers will develop into chronic hepatitis, and about 20% of chronic hepatitis patients will develop into liver cancer. HCV has become the one of serious hazard of human. Now,α-interferon orα-interferon and ribavirin combination as the only effective medicine to treat HCV, but their efficiency is only 40%. Evenly, some of the patients had serious side effects. So, in recent years, it has been the main fields that to find new and effective medicine to treat HCV.As antivirus and anticancer drugs, nucleoside analogues have attracted great attention in recent years. Ribavirin that exhibits excellent antiviral activity was the first synthetic broad-spectrum antiviral nucleoside. Six compounds of the FDΑapproved antivirus drugs (AZT, ddC, ddI, d4T, 3TC and Abacavir) belong to this class. However, the side effects of these compounds have restricted the application on the clinical. Recently, 1, 3-Dideoxynucleoside prototypes containing heteroatom within the carbohydrate framework have led to several promising antivirus activities, such as dioxolane-T and 3TC. These compounds have shown excellent antiviral activities with no significant drug resistance after one year of clinical trials. Consequently, they have become an important research field of medicine.The synthesis of 2-deoxynucleosides analogues has been achieved by 16 steps reactions from the D-xylose.Assay using the Sip-L infection system, The estimated EC50 of compound 16 was 0.6μg /mL, The IC50 was 360μg /mL. The results shown that compound 16 cound suppress HCV replication in the Sip-L assisted HCV replication system.This paper is divided into the following sections:1. Compound 6 is synthesized by D-xylose. 2. Compound 9 is synthesized by Compound 6.3. Compound 12 is synthesized by Compound 9.4. Compound 16 is synthesized by Compound 12.

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