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Title: The synthesis of novel pyrophosphate analogues and their antiviral activities
Author: Thornton, David Michael
ISNI:       0000 0001 3532 8899
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 1989
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry