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Studies of the chemistry of some 5-diazopyrimidine nucleosides

Yin, Z. (1994). Studies of the chemistry of some 5-diazopyrimidine nucleosides. (Unpublished Doctoral thesis, City, University of London)


Uridine plays a very important role in the process of de novç synthesis of DNA and RNA. Many derivatives and analogues of uridine have shown anti-cancer and anti-viral activities. A search for new uridines with potential anti-cancer and anti-viral activity is described in this thesis, which includes the preparation of novel uridine derivatives from 5-diazo-5’,6-cyclo-uridine and -deoxyuridine, and some chemical studies of the reactivity of 5-diazo-5',6-cyclo-uridines.

The results of the study are as follows:
1) The key intermediates, 5-diazo-5',6-cyclo-uridine and 5-diazo-5',6-cyclo- 2'-deoxyuridine have been synthesised in a new procedure which is more efficient and safer than the reported one.
2) A number of novel 5-aryloxy-uridines, 5-aryloxy-2'-deoxyuridines, 5- (3"-aryl-l"-triazeno)-uridines and 5-(3"-aryl-l"-triazeno)-2'-deoxyuridines have been synthesised from 5-diazo-5',6-cyclo-uridine and 5-diazo-5',6-cyclo-2'- deoxyuridine, respectively.
3) The successful synthesis of 5-diazo-6-methoxy-5'-trityl-uridine and 5- diazo-6-isopropoxy-5'-trityl-uridine provides a convenient route for the preparation of some 5-diazo-6-aryloxy-uridines and -2'-deoxyuridines, from which some 5,6- disubstituted uridines and -2'-deoxyuridines may be prepared.
4) The reactivity of 5-diazo-5',6-cyclo-uridine has been studied in some organic solvents. A new intramolecular rearrangement of 5-diazo-5',6-cyclo-2'- deoxyuridine and of the corresponding 5-diazo-5',6-cyclo-2'-uridine via carbene intermediates has been discovered.

The structures of all of twenty eight new compounds prepared in this work have been confirmed spectroscopically and biological tests on many of these compounds are in progress.

Publication Type: Thesis (Doctoral)
Subjects: Q Science > QD Chemistry
Departments: School of Science & Technology
School of Science & Technology > School of Science & Technology Doctoral Theses
Doctoral Theses
[thumbnail of Yin thesis 1994 PDF-A.pdf]
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