969. Modified steroid hormones. Part XXIX. Some 17α-chloroethynyl-17β-hydroxy-derivatives

Burgess, Christopher M.; Burn, D.; Ducker, J.W.; Ellis, B.; Feather, P.; Hiscock, A. K.; Leftwick, A. P.; Mills, John; Petrow, V.

doi:10.1039/jr9620004995

Cited by 15 publications

(2 citation statements)

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“…28 The corresponding KA value for the 17a-(iodoethynyl)estradiol could not be determined because of the instability of the com-pound29 and the value for the 17a-chloroethynyl derivative was not reported. 30 The Z isomers have the G substituent directed at a different portion of the receptor and the binding that is observed is of a different order. Receptor affinities are relatively greater at both 0 and 25 °C, and increased lipophilicity enhances the effect within the halogen series.…”

Section: Estrogen-receptor Bindingmentioning

confidence: 99%

Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17.alpha.,20E)- and (17.alpha.,20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17.beta.-diols

Napolitano¹,

Fiaschi²,

Hanson³

1991

J. Med. Chem.

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As part our program to probe the molecular requirement for estrogen-receptor binding we undertook the synthesis and evaluation of the 17 alpha,E and 17 alpha,Z halovinyl estradiols. By use of an improved variation of the existing synthetic strategy, the targeted compounds were prepared stereospecifically and in 92-98% yields from the corresponding 17 alpha,E or 17 alpha,Z [(tri-n-butylstannyl)vinyl]estradiol 3-acetates. The novel estradiol derivatives were evaluated for their relative binding affinity (RBA) for the estrogen receptor with use of a rat uterine preparation. The results demonstrated a marked difference between the E and Z isomers and among the halogen employed. The Z isomers possessed significantly higher RBA values and the larger halogens (I, Br) were more effective than the smaller Cl substituent. These results modify the previous interpretations of estrogen-receptor binding for steroidal ligands. As a result, our design of (radio)halogenated ligands will incorporate this concern for Z vs E stereochemistry.

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Section: Estrogen-receptor Bindingmentioning

confidence: 99%

Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17.alpha.,20E)- and (17.alpha.,20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17.beta.-diols

Napolitano¹,

Fiaschi²,

Hanson³

1991

J. Med. Chem.

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“…1 l), 6-chloro-3-ethoxyandrosta-3,5-diene-17-one (4c) (12), and 3-ethoxy-6-methylandrosta-3,5-diene-l7-one (4d) (13).…”

Section: Preparation Of Substratesmentioning

confidence: 99%

Microbial hydroxylation of steroids. 6. Hydroxylation of C-6-substituted androst-4-ene-3,17-diones by Rhizopusarrhizus ATCC 11145

Holland¹,

Diakow²

1979

Can. J. Chem.

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. J. Chem. 57. 1585 (1979).The products arising from the incubations of C-6a and C-6p chloro-, fluoro-, and methylsubstituted A4-3-keto steroids with the C-6b hydroxylating fungus Rllizopus arrhizus ATCC 11145 have been identified, and their formation rationalised in terms of A3s5 enolic intermediates. The incubations of C-6 chloro and methyl A3.' en01 acetates with R. arrhizus, and the oxidations by m-chloroperoxybenzoic acid of the corresponding en01 ethyl ethers have also been described. The relevance of the results so obtained to the mechanism of C-6p hydroxylation of A4-3-keto steroids by R. arrhizus is discussed.HERBERT L. HOLLAND et PETER R. P. DIAKOW. Can. J. Chem. 57, 1585 (1979).On a identifie les produits qui se forment par incubation de A4 cCto-3 stkroi'des (substituks en C-6a et C-6b par des chlore, fluor ou mCthyle) avec les champignons hydroxylant en C-6p, Rhizopus arrhizus ATCC 11 145 et l'on a rationalis6 leur formation en termes d'intermediaires Cnoliques A' s5. On dCcrit aussi les incubations des acCtates Cnoliques A3e5 substitues en C-6 par un chlore ou un mCthyle ainsi que les oxydations par l'acide m-chloroperbenzoique des Cthers Cnoliques Cthyliques correspondants. On discute de la relation entre ces risultats et le mecanisme de l'hydroxylation en C-6p des A4 &to-3 stCroldes par le R arrhizus.[Traduit par le journal]

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Study on preparation of pregna‐4‐en‐17α,21‐diol‐3,20‐dione from androst‐4‐en‐3,17‐dione

Huy,

Tu,

Diep

et al. 2021

Vietnam Journal of Chemistry

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969. Modified steroid hormones. Part XXIX. Some 17α-chloroethynyl-17β-hydroxy-derivatives

Abstract: Buygess et al. 4995 969. Modi$ed Xteroid Hormones. Part X X I X J Xome 17a -Chloroethynyl-17p -hydroxy-derivatives.

Cited by 15 publications

References 0 publications

Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17.alpha.,20E)- and (17.alpha.,20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17.beta.-diols

Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17.alpha.,20E)- and (17.alpha.,20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17.beta.-diols

Microbial hydroxylation of steroids. 6. Hydroxylation of C-6-substituted androst-4-ene-3,17-diones by Rhizopusarrhizus ATCC 11145

Study on preparation of pregna‐4‐en‐17α,21‐diol‐3,20‐dione from androst‐4‐en‐3,17‐dione

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