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

Autor(en): Rosemeyer, Helmut 
Anders, Martina
Seela, Frank
Stichwörter: ALKALINE HYDROLYSIS; ALLOPURINOL; AQUEOUS DIMETHYL SULFOXIDE; Biochemistry & Molecular Biology; Chemistry; Chemistry, Multidisciplinary; dimeric drugs; dimethylsulfoxide; ESTER SAPONIFICATION REACTIONS; PHASE-TRANSFER GLYCOSYLATION; PURINE ANTAGONISTS; PYRAZOLO<3,4-D>PYRIMIDINES; REACTION VELOCITY; SULPHOXIDE-WATER MIXTURES; XANTHINE-OXIDASE
Erscheinungsdatum: 2007
Herausgeber: MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL
Journal: MOLECULES
Volumen: 12
Ausgabe: 3
Startseite: 563
Seitenende: 575
Zusammenfassung: 
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.
ISSN: 14203049
DOI: 10.3390/12030563

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