Synthesis of thymidine analogs as potential anti-HIV inhibitors

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Title: Synthesis of thymidine analogs as potential anti-HIV inhibitors
Author: Qiu, Bingjing
Abstract: Acquired immunodificiency syndrome ( AIDS ) disease is caused by Human Immunodeficiency Virus (HIV). HIV is a retrovirus that uses reverse transcriptase ( RT ) to transcribe and translate its genetic information. Drugs including 3'-azido-3'- deoxythymidine (AZT) have been targeted at the polymerase domain of reverse transcriptase but not the ribonuclease H (RNase H) domain. Unfortunately, the lack of specificity of these drugs to the targeted enzyme has caused unavoidable side effects, which lead us to the design of active-site-directed irreversible enzyme inhibitors of both the polymerase and RNase H domains. Two thymidine analogs 5'-p-fluorosulfonylbenzamidothymidine ( 5 ) and 3'-pfluorosulfonyl- benzamidothymidine ( 10 ) with a terminal fluorosulfonylbenzamido group were synthesized and characterized. Of these two compounds, 3'-p-fluorosulfonylbenzamidothymidine has never been made before, while neither of these two compounds has been tested for its anti-HIV activity. Computational chemistry results were also presented showing the metal binding site of polymerase and RNase H domains of reverse transcriptase. Cysl81 and His539 were found at the above two domains, respectively. These two amino acids may serve as potential nucleophiles for affinity labeling by our inhibitors.
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Date: 1998-04

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