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Titolo:
Azasteroids derived from fusidic acid
Autore:
Murphy, WS; Sarsam, B; Ferguson, G; Gallagher, JE;
Indirizzi:
Natl Univ Ireland Univ Coll Cork, Dept Chem, Cork, Ireland Natl Univ Ireland Univ Coll Cork Cork Ireland Dept Chem, Cork, Ireland Univ Guelph, Dept Chem & Biochem, Guelph, ON N1G 2W1, Canada Univ Guelph Guelph ON Canada N1G 2W1 Biochem, Guelph, ON N1G 2W1, Canada
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 24, , anno: 1998,
pagine: 4121 - 4128
SICI:
0300-922X(199812):24<4121:ADFFA>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
BECKMANN REARRANGEMENT; BIOLOGICAL-ACTIVITY; ANTITUMOR-ACTIVITY; STEROIDS; 5-ALPHA-REDUCTASE; INHIBITION; ESTERS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
60
Recensione:
Indirizzi per estratti:
Indirizzo: Murphy, WS Natl Univ Ireland Univ Coll Cork, Dept Chem, Cork, Ireland NatlUniv Ireland Univ Coll Cork Cork Ireland Cork, Ireland
Citazione:
W.S. Murphy et al., "Azasteroids derived from fusidic acid", J CHEM S P1, (24), 1998, pp. 4121-4128

Abstract

The Beckmann rearrangement pathway of the (E)-11-oxime 6, derived from fusidic acid, one of the uncommon 9 beta-steroids with ring B constrained in aboat conformation, was investigated. It was found that 6 was converted into methyl 3-O-acetyl-11-aza-11a-homo-11a-oxo-24,25-dihydrofusidate 7, the 'normal' product of rearrangement, when treated with toluene-p-sulfonyl chloride in pyridine. The structure and stereochemistry of 7 was determined by X-ray crystallography. The absolute configuration of fusidic acid was confirmed. The Beckmann rearrangement of the oxime derivatives of 3- and 17-oxo-9beta-steroids derived from fusidic acid was also investigated. In general,with the exception of the (E)-oxime of 17-oxotriacetate 13b, which resulted in a complex mixture of products, none of which predominated, all the oximes gave the normal Beckmann rearrangement products.

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Documento generato il 18/11/17 alle ore 05:51:38