University of Illinois Urbana-Champaign

Syntheses of Dimensionally Altered Enzyme Substrates by Means of the Finkelstein Reaction (Benzopurine, Naphthopurine)

Stevenson, Thomas Martin

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Description

Title
Syntheses of Dimensionally Altered Enzyme Substrates by Means of the Finkelstein Reaction (Benzopurine, Naphthopurine)
Author(s)
Stevenson, Thomas Martin
Issue Date
1984
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
  • Methods for the synthesis of 9-aminobenzimidazo{5,6-g}quinazoline (lin-naphthoadenine) and 9-amino-3-(beta)-D-ribofuranosylbenzimidazo{5,6-g}quinazoline (lin-naphthoadenosine) have been developed. The synthetic route commenced with 5,6-dimethylbenzimidazole and the linear array of rings was constructed by means of the Finkelstein reaction. lin-Naphthoadenosine was synthesized by ribosidation of 9-methylthiobenzimidazo{5,6-g}quinazoline followed by ammonia displacement. Syntheses of benzimidazo{5,6-g}-8H-quinazolin-9-one (lin-naphthohypoxanthine) and benzimidazo{5,6-g}-6H,8H-quinazoline-7,9-dione (lin-naphthoxanthine) were accomplished by similar routes. lin-Naphthoadenine and lin-naphthoadenosine were both found to be highly fluorescent. Neither of these purine analogs was found to be a substrate when tested for activity with the enzyme adenosine deaminase from calf intestinal mucosa.
  • A synthetic route to imidazo{4,5-g}quinazolines (lin-benzopurines) reduced in the central ring has also been investigated. The first representative of this class of compounds, 4,7,8,9-tetrahydroimidazo{4,5-g}quinazoline-4,7-dione was synthesized from 1,3-diacetyl-4,5-dimethylimidazol-2-one in 5 steps utilizing the Finkelstein reaction to construct the tricyclic ring system.
Graduation Semester
1984
Type of Resource
text
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http://hdl.handle.net/2142/70240

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