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10000-01-01 Foster, Robert Herschel 2014-12-13T20:10:56Z 2014-12-13T20:10:56Z 1980 1980 Pyrazolo{4,3-g}quinazolin-5-one (lin-benzoallopurinol), an extended analogue of 4-hydroxypyrazolo{3,4-d}pyrimidine (allopurinol), and pyrazolo{3,4-f}quinazolin-9-one (proxbenzoisoallopurinol), an extended analogue of 7-hydroxypyrazolo{4,3-d}pyrimidine (isoallopurinol), have been synthesized. The proximal compound has been synthesized by two independent routes. Both benzo-compounds, prepared by the elaboration of suitably substituted indazoles or quinazolines, were found to be active substrates for and alternative-substrate inhibitors of xanthine oxidase. In each case, the product of enzymatic oxidation has been isolated and compared with the same material synthesized chemically. These oxidation products have been identified as the corresponding benzoalloxanthines. A synthetic route toward the synthesis of 4-amino-8-(beta)-D-ribofuranosylpyrrolo{3,2-g}quinazoline (lin-benzotubercidin), an extended analogue of the naturally occurring Streptomyces antibiotic 4-amino-7-(beta)-D-ribofuranosylpyrrolo{2,3-d}pyrimidine (tubercidin), has been explored with the synthesis of 8-(beta)-D-ribofuranosylpyrrolo{3,2-g}quinazolin-4-one (1-deaza-lin-benzoinosine) via the "indoline-indole" method. Pyrrolino{3,2-g}quinazolin-4-one, synthesized from indoline, condensed with 5-O-tritylribose to form 8-(5'-O-tritylribofuranosyl)pyrrolino{3,2-g}quinazolin-4-one. This riboside was protected, oxidized to the pyrrolo derivative with 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ), and deprotected to give 1-deaza-lin-benzoinosine. This route seems applicable to the synthesis of lin-benzotubercidin. Made available in DSpace on 2014-12-13T20:10:56Z (GMT). No. of bitstreams: 1 8026493.pdf: 4089980 bytes, checksum: 23bdf2c0bdbcbc77ecb7a7102aaee842 (MD5) Previous issue date: 1980 Embargo set by: Seth Robbins for item 67407 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 155 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980. http://hdl.handle.net/2142/67229 (UMI)AAI8026493 eng Chemistry, Organic Defined Dimensional Changes in Purine Analogues text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.