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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