Literature DB >> 17851411

Symmetrically and unsymmetrically bridged methylenebis(allopurinols): synthesis of dimeric potential anti-gout drugs.

Helmut Rosemeyer1, Martina Anders, Frank Seela.   

Abstract

Liquid-liquid phase transfer alkylation of 4-methoxy-pyrazolo[3,4-d]-pyrimidine (1a) with a dichloromethane/dibromomethane mixture (3:1, v/v) gave the regioisomeric methylenebis(heterocycles) 3a-5a. These were converted by dilute aqueous sodium hydroxide containing dimethylsulfoxide (DMSO) at concentrations between 0 and 60 vol-% into the methylenebis(allopurinols) 3b-5b by nucleophilic SNAr reactions at C(4). The effect of DMSO on the reaction kinetics was investigated.

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Year:  2007        PMID: 17851411      PMCID: PMC6149505          DOI: 10.3390/12030563

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  5 in total

1.  Stacking conformation of 9-[omega-(thymin-1-yl)alkyl]adenine in aqueous solution.

Authors:  Toshio Itahara
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2003-03       Impact factor: 1.381

2.  Kinetic properties and inhibition of orotidine 5'-phosphate decarboxylase. Effects of some allopurinol metabolites on the enzyme.

Authors:  J A Fyfe; R L Miller; T A Krenitsky
Journal:  J Biol Chem       Date:  1973-06-10       Impact factor: 5.157

3.  On the mechanism of inactivation of xanthine oxidase by allopurinol and other pyrazolo[3,4-d]pyrimidines.

Authors:  V Massey; H Komai; G Palmer; G B Elion
Journal:  J Biol Chem       Date:  1970-06-10       Impact factor: 5.157

4.  Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation.

Authors:  D J Nelson; S W LaFon; J V Tuttle; W H Miller; R L Miller; T A Krenitsky; G B Elion; R L Berens; J J Marr
Journal:  J Biol Chem       Date:  1979-11-25       Impact factor: 5.157

5.  Methylated 7-deazahypoxanthines as regiochemical probes of xanthine oxidase.

Authors:  H Rosemeyer; F Seela
Journal:  Eur J Biochem       Date:  1983-08-15
  5 in total

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