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Title:Defined Dimensional Alterations in Enzyme Substrates. Synthesis and Enzymatic Evaluation of Some Lin-Naphthopurines
Author(s):Moder, Kenneth Philip
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The development of methodology for the regioselective synthesis of tetra-beta-substituted naphthalenes via a combination of bicyclo{4.2.0}octa-1,3,5-triene and aryl trimethylsilyl chemistry led to the synthesis of benzimidazo{5,6-g}-8H-quinazolin-9-one and benzimidazo{5,6-g}-6H,8H-quinazoline-7,9-dione 4.8 (ANGSTROM) laterally extended dimensional derivatives of hypoxanthine and xanthine. These compounds, lin-naphthohypoxanthine and lin-naphthoxanthine, exhibited intense fluorescence. lin-Naphthoxanthine was not oxidized to lin-naphthouric acid by xanthine oxidase but functioned as a noncompetitive inhibitor. However, lin-naphthohypoxanthine was readily converted to lin-naphthoxanthine by xanthine oxidase. In this reaction, lin-naphthohypoxanthine functioned as a competitive inhibitor of xanthine oxidase. The enzymatic results for the naphthologs when compared with the benzologs demonstrate, in part, a useful application of defined dimensional probes for determining the limiting spatial restrictions of the binding region for xanthine oxidase.
Investigation of alternative synthetic routes to the lin-naphthopurines via preformed tetra-beta-substituted naphthalenes or other benzenoid precursors reinforced the intrinsically unfavorable substitution pattern of naphthalene and reminded us of the problems associated with the formation of halomethyl groups nitrogen-substituted aromatics. In exploring the alternative synthetic routes several 4,5-disubstituted-1,2-di(halomethyl)-benzene compounds and their potential precursors were made wherein the halogen was Cl, Br, I and the disubstitution was with H, OMe, NHAc, NHCOPh, or N(Ac)(,2).
Issue Date:1981
Type:Text
Description:159 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1981.
URI:http://hdl.handle.net/2142/70164
Other Identifier(s):(UMI)AAI8203537
Date Available in IDEALS:2014-12-15
Date Deposited:1981


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