Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 903-906 |
| Seitenumfang | 4 |
| Fachzeitschrift | Bioorganic and Medicinal Chemistry Letters |
| Jahrgang | 7 |
| Ausgabenummer | 7 |
| Publikationsstatus | Veröffentlicht - 8 Apr. 1997 |
| Extern publiziert | Ja |
Abstract
The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid γ-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled. with 1 under Mitsunobu conditions. Deprotection, i.e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of α- and β-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Biochemie, Genetik und Molekularbiologie (insg.)
- Molekularmedizin
- Biochemie, Genetik und Molekularbiologie (insg.)
- Molekularbiologie
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Pharmazeutische Wissenschaften
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Wirkstoffforschung
- Biochemie, Genetik und Molekularbiologie (insg.)
- Klinische Biochemie
- Chemie (insg.)
- Organische Chemie
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in: Bioorganic and Medicinal Chemistry Letters, Jahrgang 7, Nr. 7, 08.04.1997, S. 903-906.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000
AU - Kirschning, Andreas
AU - Ries, Monika
AU - Domann, Silvie
AU - Martin, Wolfgang
AU - Albrecht, Wolfgang
AU - Arnold, Peter
AU - Laufer, Stefan
N1 - Funding information: Support by the Fonds der Chemischen Industrie is gratefully acknowledged.
PY - 1997/4/8
Y1 - 1997/4/8
N2 - The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid γ-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled. with 1 under Mitsunobu conditions. Deprotection, i.e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of α- and β-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis.
AB - The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid γ-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled. with 1 under Mitsunobu conditions. Deprotection, i.e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of α- and β-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis.
UR - http://www.scopus.com/inward/record.url?scp=0031002781&partnerID=8YFLogxK
U2 - 10.1016/S0960-894X(97)00123-6
DO - 10.1016/S0960-894X(97)00123-6
M3 - Article
AN - SCOPUS:0031002781
VL - 7
SP - 903
EP - 906
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 7
ER -