A novel procedure for the aromatization of ring a in 19-nortestosterone

Mihalilović, M.Lj.; Forsek, J.; Lorenć, Lj.

doi:10.1016/0040-4020(77)80132-4

Cited by 9 publications

(5 citation statements)

References 4 publications

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“…The thioether derivative (19) was synthesized (Scheme 3) starting from 19-nortestosterone (16) using previously published methods (19,20). The 19-nortestosterone (16) was converted to its epoxy derivative (17) by oxidation with alkalic hydrogen peroxide.…”

Section: Resultsmentioning

confidence: 99%

“…The mercaptopropionic acid was introduced into the 4,5-epoxy-17β-hydroxyestr-1-en-3-one (18) by modifying the method of Ghaffari et al (21). The product (19) was obtained in 76% yield. The estra-1,3,5(10)-trien-3,17β-diol 4-(2-carboxyethyl)thioether (19) was characterized using 1 H NMR, 13 C NMR, IR, and UV spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…The product (19) was obtained in 76% yield. The estra-1,3,5(10)-trien-3,17β-diol 4-(2-carboxyethyl)thioether (19) was characterized using 1 H NMR, 13 C NMR, IR, and UV spectroscopy. Mass spectrometry was also used to confirm the desired structure.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Europium-Labeled Estradiol Derivatives for Time-Resolved Fluoroimmunoassays

et al. 1999

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The O-(5-carboxypentyl)-, O-(4-aminobutyl)-, O-(6-aminohexyl)oximes of 2- and 4-formylestradiol as well as the 4-carboxyethylthioether derivative of estradiol were synthesized. These estradiol derivatives were characterized using IR-, 1H-, and 13C NMR spectroscopy. All synthesized estradiol derivatives were labeled with europium chelates. These "tracers" were purified and tested in a competitive time-resolved fluoroimmunoassay with monoclonal antibody (SSI 57-2) raised against the 6-O-(carboxymethyl)oxime-bovine serum albumin derivative of estradiol. All the tested europium-labeled estradiol-4-derivatives were bound by the antibody, whereas tracers linked via position 2 were not recognized by this antibody. It was observed that tracers conjugated via C-4 gave more sensitive standard curves than tracers conjugated via C-6. Especially, the estradiol-4-thioether derivative was found to be highly useful in time-resolved fluoroimmunoassays of estradiol while using this antibody.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Europium-Labeled Estradiol Derivatives for Time-Resolved Fluoroimmunoassays

et al. 1999

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“…The final dehydrogenation to the desired epoxyenone 6 was effected with selenium dioxide in 2-methyl-2-propanol. Finally, 4/3,5/3-epoxy-17|8-hydroxyestr-1 -en-3-one (7) was prepared from 19nortestosterone by epoxidation with hydrogen peroxide to give the 4,5-epoxide of known ß configuration (Mihailovic et al, 1977), followed by dehydrogenation with selenium dioxide in 2-methyl-2-propanol.…”

Section: Resultsmentioning

confidence: 99%

“…A solution of the known 4/3,5/3-epoxy-17/3-hydroxyestran-3-one (Mihailovic et al, 1977; 600 mg, 2.1 mmol), selenium dioxide (460 mg, 4.1 mmol), and acetic acid (2 mL) in 2methyl-2-propanol (150 mL) was refluxed for 14 h under N2. The reaction was worked up and the product purified by flash chromatography as described above and crystallized from ethyl acetate/hexane to give 500 mg (83%) of the desired epoxyenone: mp 125-126 °C; [a]25D +265°( c 1.4, MeOH); IR (KBr) 3440, 3040, 2940, 1680, 1612, 1445, 1260 cm'1; NMR (CDC13) 0.83 (s, 3 H, I8-CH3), 3.25 (dd, J = 2.0 and 1.2 Hz, 2 , H-4), 3.68 (br t, 1 , H-17), 5.98 (ddd, J = 10.7, 2.0, and 1.2 Hz, 1 , H-2), 6.74 (dd, J = 10.7 and 5.3 Hz, 1 H, H-l); mass spectrum, m/z 288 (M+).…”

Section: Analytical Proceduresmentioning

confidence: 99%

Active nonaromatic intermediates in the conversion of steroidal estrogens into catechol estrogens

Quesne¹,

Abdel-Baky²,

Durga³

et al. 1986

Biochemistry

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A mechanism is proposed for mixed-function oxidase-catalyzed formation of the catechol estrogens 2-hydroxy- and 4-hydroxyestradiol from estradiol. This mechanism involves nonaromatic epoxyenones as intermediates. The isomeric 1 alpha,2 alpha-epoxy-17 beta-hydroxyestr-4-en-3-one and 1 beta,2 beta-epoxy-17 beta-hydroxyestr-4-en-3-one (the latter as its 17-acetate) were synthesized from 17 beta-hydroxy-5 alpha-estran-3-one. The isomeric 4 alpha,5 alpha-epoxy-17 beta-hydroxyestr-1-en-3-one and 4 beta,5 beta-epoxy-17 beta-hydroxyestr-1-en-3-one were prepared from 19-nortestosterone. From incubations of [6,7-3H]estradiol with microsomes from MCF-7 human breast cancer cells, which principally catalyze the formation of 2-hydroxyestradiol from estradiol, we were able to isolate a 3H-labeled product with the chromatographic properties of 1 beta, 2 beta-epoxy-17 beta-hydroxyestr-4-en-3-one (as its 17-acetate). The soluble protein fraction of homogenates of rat liver, which is devoid of estrogen 2-/4-hydroxylase activity, has been shown to catalyze the formation of 2- and 4-hydroxyestradiol from the 1 alpha,2 alpha-epoxide and from the 4 alpha,5 alpha- and 4 beta,5 beta-epoxides, respectively. We suggest that these results taken together strongly support a role for epoxyenones as intermediates in the formation of catechol estrogens.

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ChemInform Abstract: REACTIONS WITH LEAD TETRAACETATE. PART 36. A NOVEL PROCEDURE FOR THE AROMATIZATION OF RING A IN 19‐NORTESTOSTERONE

Mihailović¹,

Forsek²,

Lorenć³

1977

Chemischer Informationsdienst

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A novel procedure for the aromatization of ring a in 19-nortestosterone

Cited by 9 publications

References 4 publications

Synthesis of Novel Europium-Labeled Estradiol Derivatives for Time-Resolved Fluoroimmunoassays

Synthesis of Novel Europium-Labeled Estradiol Derivatives for Time-Resolved Fluoroimmunoassays

Active nonaromatic intermediates in the conversion of steroidal estrogens into catechol estrogens

ChemInform Abstract: REACTIONS WITH LEAD TETRAACETATE. PART 36. A NOVEL PROCEDURE FOR THE AROMATIZATION OF RING A IN 19‐NORTESTOSTERONE

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