Symmetrically and Unsymmetrically Bridged Methylenebis(allopurinols): Synthesis of Dimeric Potential Anti-Gout Drugs-Reference-Cited by-同舟云学术

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

Published:2007-03-21 Issue:3 Volume:12 Page:563-575
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Rosemeyer Helmut¹,Anders Martina¹,Seela Frank¹

Affiliation:

1. Organische Chemie I – Bioorganische Chemie, Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany

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.

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/12/3/563/pdf

Reference29 articles.

1. Potential Purine Antagonists. I. Synthesis of Some 4,6-Substituted Pyrazolo[3,4-d]pyrimidines;Robins;J. Am. Chem. Soc.,1956

2. Heilmittelchemische Untersuchungen in der heterocyclischen Reihe. 14. Mitteilung. Pyrazolo[3,4-d]pyrimidine;Schmidt;Helv. Chim. Acta,1956

3. On the Mechanism of Inactivation of Xanthine Oxidase by Allopurinol and Other Pyrazolo[3,4-d]pyrimidines;Massey;J. Biol. Chem.,1970

4. Potentiation by Inhibition of Drug Degradation: 6-Substituted Purines and Xanthine Oxidase;Elion;Biochem. Pharmacol.,1963

5. Kinetic Properties and Inhibition of Orotidine 5’-Phosphate Decarboxylase;Fyfe;J. Biol. Chem.,1973

Cited by 5 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Dimeric Drugs;Current Medicinal Chemistry;2022-05

2. Corrosion Inhibition and Adsorption Properties of Some Heterocyclic Derivatives on C-Steel Surface in HCl;Journal of Bio- and Tribo-Corrosion;2020-03-22

3. Design and Synthesis of New Aryloxy‐linked Dimeric 1,2,3‐Triazoles via Click Chemistry Approach: Biological Evaluation and Molecular Docking Study;Journal of Heterocyclic Chemistry;2019-07-02

4. Some Pyrazole and Pyrazolo[3,4‐d]pyrimidine Derivatives: Synthesis and Anticancer Evaluation;Archiv der Pharmazie;2014-05-06

5. Synthesis of 3-(4-Chloro-2-methoxy-7H-pyrrolo[2,3-d]-pyrimidin-7-yl)propanoic acid – An N(9)-Functionalized 7-Deazapurine;Molbank;2009-02-06