113424-74-1Relevant articles and documents
Synthesis of 3-Alkyl-6-Phenyl-4(3H)-pteridinones and their 8-Oxides. Potential Substrates of Xanthine Oxidase
Meester, J. W. G. De,Kraus, W.,Plas, H. C. van der,Brons, H. J.,Middelhoven, W. J.
, p. 1109 - 1116 (2007/10/02)
Synthetic routes for the preparation of 3-alkyl-6-phenyl-4(3H)-pteridinines 6 and their corresponding 8-oxides 5 (R=CH3, C2H5, (CH2)2CH3, (CH2)3CH3, CH(CH3)C2H5, CH(CH3)2 and CH(C2H5)CH2OCH(OC2H5)2) are described and their reactivities towards xanthine oxidase from Arthrobacter M-4 are determined.Only the 3-methyl derivative of 6-phenyl-4(3H)-pteridinone and its 8-oxide i.e. 6a and 5a are found to be substrates although their reactivities are still very low.Oxidation takes place at C-2 of the pteridinone nucleus.All the 3-alkyl derivatives are less tightly bound to t he enzyme than 6-phenyl-4(3H)-pteridinone.Introduction of the N-oxide at N-8 considerably lowers the binding of the substrates.Inhibition studies have revealed that 3-methyl-6-phenyl-4(3H)-pteridinone (6a) is non-competitive inhibitor with a Ki-value of 47 μM and the 3-ethyl derivative (6b) an uncompetitive one with a Ki-value of 19.6 μM.
