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.
Record URI: http://hdl.handle.net/1850/13947
Date: 1998-04

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