Synthesis of the Androgen-Receptor Antagonists (±)-Ws9761 A and B

Cameron, D. W.; Skene, CE

doi:10.1071/ch9960617

Cited by 13 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These results support the hypothesis that the antiandrogenic effects of DDT on the male reproductive system are mediated by p,p'-DDE [138]. Compounds 155 and 156, isolated from the fermentation broth of a Streptomyces strain microorganism, were moderately active as antiandrogens [139,140]. In DDT1 cells, L-245976 (157) completely blocked the action of testosterone (10 nM) at 10 µM, whereas hydroxyflutamide at 1 µM had a similar effect.…”

Section: Cyclocymopolsupporting

confidence: 79%

Androgen Receptor Antagonists (Antiandrogens) Structure-Activity Relationships

Singh

Gauthier²,

Labrie

2000

CMC

213

162

View full text Add to dashboard Cite

Prostate cancer, acne, seborrhea, hirsutism, and androgenic alopecia are well recognized to depend upon an excess or increased sensitivity to androgens or to be at least sensitive to androgens. It thus seems logical to use antiandrogens as therapeutic agents to prevent androgens from binding to the androgen receptor. The two predominant naturally occurring androgens are testosterone (T) and dihydrotestosterone (DHT). DHT is the more potent androgen in vivo and in vitro. All androgen-responsive genes are activated by androgen receptor (AR) bound to either T or DHT and it is believed that AR is more transcriptionally active when bound to DHT than T. The two classes of antiandrogens, presently available, are the steroidal derivatives, all of which possess mixed agonistic and antagonistic activities, and the pure non-steroidal antiandrogens of the class of flutamide and its derivatives. The intrinsic androgenic, estrogenic and glucocorticoid activities of steroidal derivatives have limited their use in the treatment of prostate cancer. The non-steroidal flutamide and its derivatives display pure antiandrogenic activity, without exerting agonistic or any other hormonal activity. Flutamide (89) and its derivatives, Casodex (108) and Anandron (114), are highly effective in the treatment of prostate cancer. The combination of flutamide and Anandron with castration has shown prolongation of life in prostate cancer. Furthermore, combined androgen blockade in association with radical prostatectomy or radiotherapy are very effective in the treatment of localized prostate cancer. Such an approach certainly raises the hope of a further improvement in prostate cancer therapy. However, all antiandrogens, developed so-far display moderate affinity for the androgen receptor, and thus moderate efficacy in vitro and in vivo. There is thus a need for next-generation antiandrogens, which could display an equal or even higher affinity for AR compared to the natural androgens, and at the same time maintain its pure antiandrogenic activity, and thus providing improved androgen blockade using possibly antiandrogens alone.

show abstract

Section: Cyclocymopolsupporting

confidence: 79%

Androgen Receptor Antagonists (Antiandrogens) Structure-Activity Relationships

Singh

Gauthier²,

Labrie

2000

CMC

213

162

View full text Add to dashboard Cite

show abstract

“…3,4 Several such substances have noteworthy biological characteristics and are utilized as antimicrobial, emetic, antipsoriatic or androgen receptors and telomerase blockers. 5,6 Recent studies have demonstrated that some anthrone-or anthraquinone-based naturally occurring compounds show strong and distinctive antitumor behaviours. [7][8][9][10][11] The Michael reaction of carbon-centered nucleophiles with different Michael acceptors provides a straightforward and robust technique for the formation of C-C bonds and has received prevalent preference in the production of organic materials.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Michael reaction of anthrone catalyzed by chiral tetraoxacalix[2]arene[2]triazine derivatives

Genc

2019

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…Finally, 9-oxoanthracene has been used in the determination of sugars. Moreover, many members of the anthrone family have interesting biological properties (e.g., antimicrobials, laxatives, antipsoriatics, telomerase inhibitors or selective antitumor activity) 15 16 17 18 19 .…”

mentioning

confidence: 99%