{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70240"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70240","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Syntheses of Dimensionally Altered Enzyme Substrates by Means of the Finkelstein Reaction (Benzopurine, Naphthopurine)","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Stevenson, Thomas Martin"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-15T23:18:05Z","date_published":"2014-12-15T23:18:05Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8409838"],"render_values":[{"text":"(UMI)AAI8409838","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70240","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Stevenson, Thomas Martin"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T23:18:05Z","10000-01-01","1984"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/70240","(UMI)AAI8409838"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["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.","Made available in DSpace on 2014-12-15T23:18:05Z (GMT). No. of bitstreams: 1 8409838.pdf: 2878817 bytes, checksum: 74f1d82e709ec18aee7f477c310e32cd (MD5) Previous issue date: 1984","Embargo set by: Seth Robbins for item 70406 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","122 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984."]},{"key":"dc:title","label":"Title","values":["Syntheses of Dimensionally Altered Enzyme Substrates by Means of the Finkelstein Reaction (Benzopurine, Naphthopurine)"]}]}],"canonical_facts":{"dc:creator":["Stevenson, Thomas Martin"],"dc:date":["2014-12-15T23:18:05Z","10000-01-01","1984"],"dc:description":["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.","Made available in DSpace on 2014-12-15T23:18:05Z (GMT). No. of bitstreams: 1 8409838.pdf: 2878817 bytes, checksum: 74f1d82e709ec18aee7f477c310e32cd (MD5) Previous issue date: 1984","Embargo set by: Seth Robbins for item 70406 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","122 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984."],"dc:identifier":["http://hdl.handle.net/2142/70240","(UMI)AAI8409838"],"dc:subject":["Chemistry, Organic"],"dc:title":["Syntheses of Dimensionally Altered Enzyme Substrates by Means of the Finkelstein Reaction (Benzopurine, Naphthopurine)"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:02Z"}