The synthesis of the glucuronide adduct of Trocade (TM)

Authors
Mitchell, MB Whitcombe, IWA
Citation
Mb. Mitchell et Iwa. Whitcombe, The synthesis of the glucuronide adduct of Trocade (TM), TETRAHEDR L, 41(45), 2000, pp. 8829-8834
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
45
Year of publication
2000
Pages
8829 - 8834
Database
ISI
SICI code
0040-4039(20001104)41:45<8829:TSOTGA>2.0.ZU;2-W
Abstract
The synthetic preparation of the glucuronide adduct of Trocade(TM), a selec tive inhibitor of the MMP collagenase, is described. This was achieved by p reparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. Th e synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the h ydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.