Mikrobiologische Herstellung von 1‐Dehydro‐Steroiden. Mikrobiologische Reaktionen, 6. Mitteilung

Abstract

Volumen XXYVITT, Fasciculus 111 (1955) -No. 04. 835 94. Mikrobiologische Herstellung von l-Dehydro-Steroiden I). Mikrobiologische Reaktionen, 6. Mitteilung2) von E. Vischer, Ch. Meystre und A. Wettstein. (31. 111. 55.)In letzter Zeit haben das l-Dehydro-cortison und das 1-Dehydro-1 7cr-oxy-corticosteron3) wegen ihrer anti-arthritischen Wirkung grossea Interesse gefunden. Wir berichten deshalb neuerdings iiber die mikrobiologische Herstellung von l-Dehydro-Steroiden.Die dehydrierende Einfuhrung einer 1,2-DoppeIbindung i m Ring A von Steroiden mittels gewissen Schimmelpilzen der Gattung Fusarium haben wir 1953 be~chrieben~). Bei 17-Desoxy-20-oxo-Verbindungen trat gleichzeitig Seitenketten-Abbau zum 17-Keton ein. So konnten z. B. Progesteron, Cortexon (ll-Desoxy-corticosteron) sowie d *-Androsten-3,1i'-dion in guter Ausbeute in das ~ll,~-Androstadien-3,17-dion ubergefuhrt werden. Wir wiesen damals darauf hin, dass 17c(-Oxy-20-oxo-pregnene, wie Cortison und 17~-Oxy-cortexon (Reichstein's Substanz S), von diesen Pilzen in der Seitenkette niche abgebaut, sondern in ,,weitere Substanzen" iibergefihrt werden. Diese Umwandlungsprodukte liessen sich nun als die entspreehenden 2) 5. Mitt. s. Helv. 38, 381 (1955).

Mass spectrometric identification and characterization of a new long‐term metabolite of metandienone in human urine

“…4 Compounds such as methyltestosterone or metandienone (Scheme 1, 1 and 2) have been synthesized 5,6 and investigated regarding metabolic pathways, pharmacokinetic parameters and anabolic as well as androgenic effects on humans. 7-13 The metabolism of metandienone has been investigated in detail providing the basis for all commonly accepted and employed screening and confirmation procedures for this particular drug in doping controls 8,14-16 using gas chromatography (GC) interfaced to low-or high-resolution mass spectrometry (MS).…”

Microbiological transformation of steroids. 1-Dehydrogenation of 17,21-dihydroxypregn-4-ene-3,20-dione with Glomerella cingulata

“…The solvent was evaporated and the residue dissolved in acetone; the solution was concentrated to a small volume and left to crystallize overnight at 0°C. The filteredcrystals were washed with a little cold acetone and recrystallized to constant m.p., 230-2340C (decomp., Kofler, uncorrected 17,21-dihydroxypregn-4-ene-3,20-dione is +485' (Vischer et al, 1955a) and the contribution of the 1,2-double bond to the molecular optical rotation is -220°. The product had i.r.…”

“…The microbiological dehydrogenation of 17,21-dihydroxypregn-4-ene-3,20-dione (I) (Reichstein's compound S) to 17,21-dihydroxypregna-1,4-diene-3,20-dione (II) (Scheme 1) by fungi of the genus Fusarium (Fusarium solani) and species of the genera Calonectria, Ophiobolus and Alternaria was reported by Vischer et al (1955a). In a later paper the same authors describe how they obtained compound II by using fungi of the genus Didymella (Didymella lycopersici Kelb) (Vischer et al, 1955b).…”

Combined Assay, Identification, and Foreign Related Steroids Test for Methandrostenolone by High‐Speed Liquid Chromatography

“…It may be synthesized from methyltestosterone (17/3-hydroxy-17a-methylandrost-4-en-$one) (11) either microbiologically (3) or chemically (4). Steroidal impurities which may be present (5) are 11, 6a,l7~-dihydroxy-17a-methylandrosta-l,4-dien- 3-one (III), and 6~,17~-dihydroxy-17au-rnethylandrosta-1,4-dien-3-one (IV). Of these, I1 has about twice the oral androgenic potency and about one-half of the anabolic activity of methandrostenolone (6).…”