A NEW CLASS OF ACTIVE STEROIDS: THE 19-NOR-[UNK]<sup>4,9</sup>-3-KETOSTEROIDS

Perelman, Mel; Farkas, Eugene; Fornefeld, E. J.; Kraay, Russell J.; Rapala, Richard T.

doi:10.1021/ja01494a082

Cited by 52 publications

(16 citation statements)

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“…As authentic samples for identification and starting materials for partial synthesis, the following compounds were prepared by published methods: (4R) -4-[4a -(2 -carboxyethyl) -3aahexahydro -7af8methyl-5-oxoindan-lf-yl]valeric acid (Ha) and its dimethyl ester (Hayakawa et al, 1969b) (Hayakawa et al, 1976a); 17.8-acetoxyoestra-4,9-dien-3-one (VI) Vol. 160 (Perelman et al, 1960;Perelman & Farkas, 1963).…”

Section: Other Materialsmentioning

confidence: 99%

Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Hayakawa

Hashimoto

Onaka

1976

Biochemical Journal

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The metabolism of cholic acid (I) by Streptomyces rubescens was investigated. This organism effected ring A cleavage, side-chain shortening and amide bond formation and gave the following metabolites: (4R)-4-[4alpha-(2-carboxyethyl)-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-1 beta-yl]valeric acid (IIa) and its mono-amide (valeramide) (IIb); and 2,3,4,6, 6abeta,7,8,9,9aalpha,9bbeta-decahydro-6abeta-methyl-1H-cyclopenta[f]quinoline-3,7-dione(IIIe)and its homologues with the beta-oriented side chains, valeric acid, valeramide, butanone and propionic acid, in the place of the oxo group at C-7, i.e.compounds (IIIa), (IIIb), (IIIc) and (IIId) respectively. All the nitrogenous metabolites were new compounds, and their structures were established by partial synthesis except for the metabolite (IIIc). The mechanism of formation of these metabolites is considered. A degradative pathway of cholic acid (I) into the metabolites is also tentatively proposed.

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Section: Other Materialsmentioning

confidence: 99%

Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Hayakawa

Hashimoto

Onaka

1976

Biochemical Journal

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“…However, the purification of compound (VIII) presented certain difficulties and compound (VII) was converted into 24hydroxy-19-norchola-4,9-dien-3-one (IXa) without the isolation of compound (VIII). A conversion of compound (VIII) into compound (IXa) was carried out essentially as reported by Perelman, Farkas, Fornefeld, Kraay & Rapala (1960) with the use of trimethylphenylammonium perbromide (Marquet et al 1961) instead of pyridinium bromide perbromide. The presence of a A\4,9-3-oxo structure in compound (IXa) was demonstrated by the u.v.absorption maximum at 306-5nm.…”

mentioning

confidence: 99%

“…spectrum (cf. Perelman et al 1960). The dienone (IXa) was converted into the acetate (IXb) with cold acetic anhydride-pyridine, which with ozone and hydrogen peroxide gave 3-{1l,-[(1R)-4-acetoxy-1 -methylbutyl] -3aca-hexahydro -7afl-methyl -5-oxoindan-4a-yl}propionic acid (Xa).…”

mentioning

confidence: 99%

Microbiological degradation of bile acids. Ring a cleavage and 7α,12α-dehydroxylation of cholic acid by Arthrobacter simplex

Hayakawa

Kanematsu

Fujiwara

1969

Biochemical Journal

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The metabolism of cholic acid by Arthrobacter simplex was investigated. This organism effected both ring a cleavage and elimination of the hydroxyl groups at C-7 and C-12 and gave a new metabolite, (4R)-4-[4alpha-(2-carboxyethyl)-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-1beta-yl]valeric acid, which was isolated and identified through its partial synthesis. A degradative pathway of cholic acid into this metabolite is tentatively proposed, and the possibility that the proposed pathway could be extended to the cholic acid degradation by other microorganisms besides A. simplex is discussed. The possibility that the observed reactions in vitro could occur during the metabolism of bile acids in vivo is considered.

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“…Cyclization was effected by treatment with sodium f-amylate and the resulting triene, on saponification and oxidation afforded the diketone 60. In still another modification [52] the hydroxyketone 55, obtained during the Birch reduction of 54, could be converted to the diene 57 by following the method of Perelman and co-workers [60]. A one-step bromination of the 5(10)-3-ketone 55 led to the A 4 -9 -analog, treatment of which with chromium trioxide yielded the diketone 57.…”

Section: -Norprogesterone and 11-hydroxy Steroidsmentioning

confidence: 99%

Bc → BCD → Abcd

1974

Organic Chemistry: A Series of Monographs

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A NEW CLASS OF ACTIVE STEROIDS: THE 19-NOR-[UNK]^4,9-3-KETOSTEROIDS

Cited by 52 publications

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Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Microbiological degradation of bile acids. Ring a cleavage and 7α,12α-dehydroxylation of cholic acid by Arthrobacter simplex

Bc → BCD → Abcd

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A NEW CLASS OF ACTIVE STEROIDS: THE 19-NOR-[UNK]4,9-3-KETOSTEROIDS

Cited by 52 publications

References 0 publications

Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

Microbiological degradation of bile acids. Ring a cleavage and 7α,12α-dehydroxylation of cholic acid by Arthrobacter simplex

Bc → BCD → Abcd

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A NEW CLASS OF ACTIVE STEROIDS: THE 19-NOR-[UNK]^4,9-3-KETOSTEROIDS