CiNii Articles - 3-Oxo-steroid

1

Conversion of 3-oxo steroids into ecdysteroids triggers molting and expression of 20E-inducible genes in Drosophila melanogaster.

Ono Hajime , Morita Sayo , Asakura Ichiyoh , Nishida Ritsuo

… Ecdysteroids, steroid hormones in insects, coordinate major developmental transitions. … We found that two 3-oxo steroids, cholesta-4, 7-diene-3, 6-dione-14α-ol (Δ(4)-diketol) and 5β [H]cholesta-7-ene-3, 6-dione-14α-ol (diketol), triggered molting of the RNAi-treated larvae. …

Biochemical and biophysical research communications 421(3), 561-566, 2012-05-11

IR
2

Reactions of Enolizable Steroidal 4-En-3-ones and 17-Ones with Hypervalent Iodine

NUMAZAWA MITSUTERU , MUTSUMI AYAKO , OGATA MIEKO

… Reaction of the 3-oxo-4-androsten-derivative 1 or 4 with 1.2eq of o-iodosylbenzoic acid in methanolic KOH gave the methoxy products, the 4-methoxide 2 or 5 and the 6β-methoxide 3 or 6,along with the dehydrated compound, the 4,6-dienone 7 or 8,respectively. … Treatment of the 6-methoxide 3 or 6 with trimethylsilyl iodide yielded the 5α-androstane-3,6-dioxo derivative 11 or 12 in high yield. …

Chemical & pharmaceutical bulletin 36(9), 3381-3386, 1988-09-25
3

Metabolism of 16α-OH Steroid in Human Placenta in vitro : Specificity of Enzyme for Steroid Biosynthesis [in Japanese]

SAKURAI Hiroshi , HIGUCHI Kazumi , SUZUKI Tomoko , HIRATO Kumiko , MATSUHASHI Kazuo , YANAIHARA Takumi , NAKAYAMA Tetsuya , IIDA Mitsugi

… 胎児・胎盤系に大量に存在するΔ^5-C19 steroidは主に胎児に由来し,胎盤でestrogen生成の材料となる.Δ^5-C19 steroidがestrogenに転換されるためには3β-hydroxysteroid dehydrogenase(3β-HSD),17β-hyd-roxysteroid dehydrogenase(17β-HSD)及びaromatizing enzyme等の各種酵素を必要とすることが知られている.この胎児性Δ^5-C19 steroidには既に16α-hydroxylationを受けたものと受けないも …

Acta obstetrica et gynaecologica Japonica 31(10), p1771-1778, 1979-10

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4

1,4-Addition of vinylmagnesium bromide to .ALPHA.,.BETA.-unsaturated steroidal ketones. II. Reaction of 1-En-3-oxo steroids.

MORI HIROMU , OHUCHI RIKIO

… The reaction of 1-en-3-oxo A/B trans steroid with vinylmagnesium bromide in the presence of cupric acetate afforded 1α-vinyl-3-oxo steroid. … The stereochemistry of the reduction of 1α-alkyl-3-oxo steroids and 5β-alkyl-3-oxo steroids with complex metal hydride was also studied. …

Chemical and Pharmaceutical Bulletin 23(5), 980-986, 1975

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5

Synthesis of Exdysone.I.A Novel Synthesis of 2β, 3β-Dihydroxy Steroids

Mori Hiromu , Shibata Kenyu , Tsuneda Kiyoshi , Sawai Masanobu

… A novel synthesis of 2β, 3β-dihydroxy steroids from 3-oxo compounds in 5α-series was developed. … Autoxidation of 3-oxo compound afforded an enol mixture of 2, 3-dioxo compound, which on reduction with sodium borohydride yielded 2β, 3β-dihydroxy steroid. …

Chemical and Pharmaceutical Bulletin 15(4), 460-465, 1967

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6

40 SYNTHESIS OF ECDYSONE (II) [in Japanese]

Mori H. , Shibata K. , Tsuneda K. , Sawai M.

… a) The enol form of 2,3-diketone (3) which is easily obtainable from 3-oxo steroid could be reduced by sodium borohydride into 2β,3β-diol (4) as a major product. … Acetonide of 2β,3β-dihydroxy-5α-cholestan-6-one (27) was prepared through two routes (22→23→24→25→27 and 28→29→30→31→32→27) by using the key reaction described above. …

Symposium on the Chemistry of Natural Products, symposium papers 10(0), 302-309, 1966

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7

36. 1,4,4-Trimethyl-3-oxo Steroidの合成およびそのConformationについて [in Japanese]

森弘 , 常田清

Symposium on the Chemistry of Natural Products, symposium papers 9(0), 210-214, 1965

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8

Conversion of 17α-Ethynyl-4-Estrene- 17β-ol to 17α-Ethynyl-19-Nortestosterone in Rabbit Liver [in Japanese]

OKADA Hiroji , OTA Satoru , TAKE Hirohiko , YAMAMOTO Hiroshi

… 活性SteroidのC<SUB>3</SUB>に認められるoxygen functionは古くからsteroidが生物学的活性を示すための重要な要素であると考えられてきたが,最近いくつかの3-deoxo-steroidやnon-steroidal perhydrophenan-threne derivativeなどが著明な生物学的活性を示すことから, C<SUB>3</SUB>のoxygen functionの重要性に疑問が持たれるに至つた.<BR …

Folia Endocrinologica Japonica 40(8), 1095-1098,1047, 1964

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9

Studies on Steroidal Compounds. VIII. A New Synthesis of 4-Chloro-4-en-3-oxo-steroids.

Mori Hiromu

… 4-En-3-oxo-steroid is converted into 4-chloro-4-en-3-oxo-steroid by treatment with sulfuryl chloride in pyridine. …

Chemical and Pharmaceutical Bulletin 10(5), 429-432, 1962

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