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The synthesis of novel pyrophosphate analogues and their antiviral activities
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Thornton, David Michael (1989) The synthesis of novel pyrophosphate analogues and their antiviral activities. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b3156706~S15
Abstract
Several methods for the preparation of novel substituted methylene-bisphosphonates were examined. A new synthesis of monofluoromethylene-bisphosphonic acid was developed involving the in situ nucleophilic debromination of tetraisopropyl bromofluoromethylenebisphosphonate. The Michael reaction of tetraalkyl ethenylidenebisphosphonates with alkanethiols was shown to be a facile method of preparation of C- (thioalkyl)methyl methylenebisphosphonates. Tetraisopropyl cyclopropane-1,1-bisphosphonate was synthesised via an intramolecular alkylation of a thallium(I) salt. Thallium(I) salts of methylenebisphosphonates were also used in the synthesis of bisphosphonates related to arildone.
The reaction of trialkyl phosphites with thiophosgene was investigated and it was shown that in THF at low temperature thio- carbonylbisphosphonate was not formed but that phosphorus stabilised ylids were the principal products.
The bisphosphonates prepared were tested for inhibitory effect against the RNA polymerase of influenza A/X49; bisphosphonates with electron-withdrawing bridge substituents showing most inhibition. Selected bisphosphonates were found to have slight activity against the reverse transcriptase of HTLV-III; the causative agent of AIDS.
Item Type: | Thesis (PhD) | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Antiviral agents -- Development, Influenza viruses -- Prevention, RNA polymerases, Pyrophosphates -- Synthesis, Diphosphonates -- Synthesis | ||||
Official Date: | February 1989 | ||||
Dates: |
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Institution: | University of Warwick | ||||
Theses Department: | Department of Chemistry | ||||
Thesis Type: | PhD | ||||
Publication Status: | Unpublished | ||||
Supervisor(s)/Advisor: | Hutchinson, D. W. (David Wesley) | ||||
Format of File: | |||||
Extent: | 146 leaves : illustrations, charts | ||||
Language: | eng |
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