A new synthesis of the benzofuran adenosine antagonist XH-14

• Published in: Bioorganic & medicinal chemistry letters Vol. 7; no. 24; pp. 3081 - 3084
• Main Authors: Hutchinson, Sally A., Luetjens, Henning, Scammells, Peter J.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 16.12.1997; Elsevier
• Subjects: Biological and medical sciences; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Medical sciences; Neuropharmacology; Neurotransmitters. Neurotransmission. Receptors; Organic chemistry; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems; Pharmacology. Drug treatments; Preparations and properties; Bicyclic compound; A1 Adenosine receptor; Benzenic compound; Aromatic compound; Antagonist; Aldehyde; Oxygen heterocycle; Chemical synthesis; Primary alcohol
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(97)10173-1

5-(3-Hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)benzo[ b]furan-3-carbaldehyde (XH-14, 1) has been reported to be a potent A 1 adenosine antagonist. We have developed an efficient synthesis of this compound that should prove valuable for further structure-activity studies. The synthesis incorporates optimised methodology for the selective protection of a hydroxyl group and the ortho-bromination of a phenol. 5-(3-Hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl) benzo[ b]furan-3-carbaldehyde (XH-14, 1) has been reported to be a potent A 1 adenosine antagonist. We have developed an efficient synthesis of this compound which should prove valuable for further structure-activity studies. The synthesis incorporates optimised methodology for the selective protection of a hydroxyl group in the presence of a phenol and the ortho-bromination of a phenol.