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Molecules 2007, 12(3), 563-575; doi:10.3390/12030563
Article

Symmetrically and Unsymmetrically Bridged Methylenebis(allopurinols): Synthesis of Dimeric Potential Anti-Gout Drugs

1,* , 1 and 1
1 Organische Chemie I – Bioorganische Chemie, Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany 2 Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstr. 11, D-48149 Münster, Germany
* Author to whom correspondence should be addressed.
Received: 9 March 2007 / Revised: 19 March 2007 / Accepted: 19 March 2007 / Published: 21 March 2007
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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.
Keywords: Allopurinol; dimethylsulfoxide; dimeric drugs Allopurinol; dimethylsulfoxide; dimeric drugs
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Rosemeyer, H.; Anders, M.; Seela, F. Symmetrically and Unsymmetrically Bridged Methylenebis(allopurinols): Synthesis of Dimeric Potential Anti-Gout Drugs. Molecules 2007, 12, 563-575.

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