Synthesis and antiandrogenic activity of 16.BETA.-substituted-17.BETA.-hydroxysteroids.

Goto, Giichi; Yoshioka, Kōta; Hiraga, Keijiro; Masuoka, Michio; Nakayama, Ryo; Miki, Takuichi

doi:10.1248/cpb.26.1718

Cited by 28 publications

(7 citation statements)

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“…TSAA-291 and its related compounds were synthesized in our laboratory (Goto et al 1977;Goto et al 1978).…”

Section: Chemicalsmentioning

confidence: 99%

“…The relative displacing potencies of various derivatives or analogues of TSAA-291 having substituent in the vicinity of C-17 listed in Table 2 were in¬ terpreted in terms of the correlation with their anti-androgenic activities, which had been assayed in our laboratory by the weight decreasing effect on the ventral prostate and seminal vesicle of castrated immature rats treated with testosterone propionate and some of which were reported elsewhere (Goto et al 1978). …”

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confidence: 99%

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VI. EFFECTS OF THE ANTI-ANDROGEN TSAA-291 AND ITS RELATED COMPOUNDS ON THE IN VITRO FORMATION OF 5α-DHT-Receptor COMPLEX IN THE CYTOSOL OF RAT VENTRAL PROSTATES

Sudo

Yoshida

Nakayama

1979

Acta Endocrinologica

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Inhibitory effect of a synthetic steroidal anti-androgen (16\g=b\-ethyl-17\g=b\-hydroxy-4-oestren-3-one) on the in vitro formation of 5\g=a\-dihydrotestosterone(5\g=a\-DHT)-receptorcomplex was examined. An aliquot of the cytosol from rat ventral prostates was incubated with [3H]5\g=a\-DHT in the presence of various amounts of the anti\x=req-\ androgen.By means of dextran-coated charcoal assay and sucrose density-gradient centrifugation analysis, TSAA-291 was demonstrated to inhibit directly, in a competitive manner, the binding of 5\g=a\-DHT to a component analogous in its properties to the cytosol androgen receptor.Further, displacing study using a variety of TSAA-291 analogues was undertaken to examine which of the functional groups of TSAA-291 is important for the affinity to the 5\g=a\-DHT binding component, and elucidated that 3-hydroxy or 5\g=a\-dihydro derivatives of TSAA-291 and others having axial methyl group at C-10 were less potent competitors for [3H]5\g=a\-DHTbinding than TSAA-291. Furthermore, using other steroids including androgens and anti-androgens, considerable knowledge was obtained about structural requirements for a steroid molecule to displace the bound [3H] 5\g=a\-DHT, and this displacing activity of the steroids was discussed in terms of their anti-androgenic activity. © © © C ©

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“…TSAA-291 and its related compounds were synthesized in our laboratory (Goto et al 1977;Goto et al 1978).…”

Section: Chemicalsmentioning

confidence: 99%

mentioning

confidence: 99%

VI. EFFECTS OF THE ANTI-ANDROGEN TSAA-291 AND ITS RELATED COMPOUNDS ON THE IN VITRO FORMATION OF 5α-DHT-Receptor COMPLEX IN THE CYTOSOL OF RAT VENTRAL PROSTATES

Sudo

Yoshida

Nakayama

1979

Acta Endocrinologica

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“…1) which were synthesized in the Chemical Section in our Research Laboratories (Goto et al 1977(Goto et al , 1978. 1) which were synthesized in the Chemical Section in our Research Laboratories (Goto et al 1977(Goto et al , 1978.…”

Section: Chemicalsmentioning

confidence: 99%

“…Based on the knowledge of the structural requirement of the steroid molecule for the 17ß-hydroxy group to manifest the androgenicity (Bush 1962;Nakayama et al 1979) together with the knowledge of the steric hindrance effect of a bulky group on the functional group in the molecule (Fieser & Fieser 1948;Newman 1956), we have designed ) and synthesized (Hiraga et al 1965; Goto et al 1977Goto et al , 1978 a new type of anti-androgenic compounds as a therapeutics with less adverse-effects for the treatment of human prostatic hyperplasias, hirsutism, acne, and so forth.…”

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confidence: 99%

I. ANTI-ANDROGENIC EFFECTS OF a NEW STEROID TSAA-291 (16β-Ethyl-17β-Hydroxy-4-Oestren-3-One) AND ITS DERIVATIVES

Nakayama¹,

Masuoka²,

Masaki³

et al. 1979

Acta Endocrinologica

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Anti-androgenic properties of newly synthesized steroidal compounds, TSAA-291* and its derivatives, were studied in the rat.(1) Subcutaneous administrations of TSAA-291 and TSAA-272* were effective in depressing the weight of seminal vesicles and ventral and dorsal prostates in the adult rat.(2) TSAA-291, TSAA-328* and TSAA-272 were shown to be anti-androgenic by the subcutaneous or oral route in the immature castrated male rat treated with testosterone

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“…TSAA-291 (16β-ethyl-17β-hydroxyestr-4-en-3-one) and TSAA-272 (17β-hydroxy-16β-isopropyl-estr-4-en-3-one) were synthesized in our company (Goto et al, 1978).…”

Section: Reagentsmentioning

confidence: 99%

Selective androgen receptor modulator activity of a steroidal antiandrogen TSAA-291 and its cofactor recruitment profile

Hikichi

Yamaoka

Kusaka

et al. 2015

European Journal of Pharmacology

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Synthesis and antiandrogenic activity of 16.BETA.-substituted-17.BETA.-hydroxysteroids.

Cited by 28 publications

References 0 publications

VI. EFFECTS OF THE ANTI-ANDROGEN TSAA-291 AND ITS RELATED COMPOUNDS ON THE IN VITRO FORMATION OF 5α-DHT-Receptor COMPLEX IN THE CYTOSOL OF RAT VENTRAL PROSTATES

VI. EFFECTS OF THE ANTI-ANDROGEN TSAA-291 AND ITS RELATED COMPOUNDS ON THE IN VITRO FORMATION OF 5α-DHT-Receptor COMPLEX IN THE CYTOSOL OF RAT VENTRAL PROSTATES

I. ANTI-ANDROGENIC EFFECTS OF a NEW STEROID TSAA-291 (16β-Ethyl-17β-Hydroxy-4-Oestren-3-One) AND ITS DERIVATIVES

Selective androgen receptor modulator activity of a steroidal antiandrogen TSAA-291 and its cofactor recruitment profile

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