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

doi:10.3390/12030563

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

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

Helmut Rosemeyer^1,* , Martina Anders¹ and Frank Seela¹

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; in revised form: 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

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MDPI and ACS Style

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

AMA Style

Rosemeyer H, Anders M, Seela F. Symmetrically and Unsymmetrically Bridged Methylenebis(allopurinols): Synthesis of Dimeric Potential Anti-Gout Drugs. Molecules. 2007; 12(3):563-575.

Chicago/Turabian Style

Rosemeyer, Helmut; Anders, Martina; Seela, Frank. 2007. "Symmetrically and Unsymmetrically Bridged Methylenebis(allopurinols): Synthesis of Dimeric Potential Anti-Gout Drugs." Molecules 12, no. 3: 563-575.

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