174505-12-5

Basic information

• Product Name: (8S,9R,10R,11S,13S,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione
• Synonyms: (8S,9R,10R,11S,13S,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione
• CAS NO: 174505-12-5
• Molecular Weight: 392.538
• Mol File: 174505-12-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (8S,9R,10R,11S,13S,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (8S,9R,10R,11S,13S,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione(174505-12-5)
• EPA Substance Registry System: (8S,9R,10R,11S,13S,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione(174505-12-5)

Safety Data

• Hazardous Substances Data: 174505-12-5(Hazardous Substances Data)

Upstream product

• 174505-06-7 5-hydroxy-11β-(4-methoxyphenyl)-11α,12α-epoxy-5α-androstane-3,17-dione cyclic bis(1,2-ethanediyl acetal) 
• 174505-09-0 (5’R,8’S,9’R,10'R,11'S,12'S,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyldodecahydro-2’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]-5’,12’(4’H)-diol 
• 174505-01-2 (8'S,9’S,10'R,13’R,14'S)-10’,13’-dimethyl-11’-(((4,4,4,4,4,4,4,4,4-nonafluoro-4112-buta-1,3-diyn-1-yl)thio)trioxidanyl)-1‘,4’,7’,8’,9’,10’, 13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[a]phenanthrene-17',2”-[1,3]dioxolane] 
• 174505-04-5 (5’R,8’S,9’R,10'R,13’R,14'S)-11’-(4-methoxyphenyl)-10’,13’-dimethyl-1‘,6’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3 ]dioxolan]-5’(4’H)-ol 
• 174505-03-4 (4a’R, 5a’S,6a’S,6b’S,9a’R,11a’R,11b’R)-11‘-(4-methoxyphenyl)-9a’,11b’-dimethyl-1’,5a’,6’,6a’,6b’,7’,8’,9a’,11a',11b’-decahydro-2’H,4’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[1,2]phenanthro[8a,9-b]oxirene-9’,2”-[1,3]dioxolane] 
• 174505-02-3 (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane] 
• 174505-10-3 (8S,9R,10R,11S,12S,13R,14S)-12-hydroxy-11-(4-methoxyphenyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione 
• 13872-18-9 (8'S,9’S,10'R,13’S,14'S)-10’,13’-dimethyl-1',2',4',7',8',9',10’,12’,13’,14',15’,16’-dodecahydro-11’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolan]-11‘-one 
• 5720-07-0 4-methoxyphenylboronic acid 
• 174505-11-4 O-((8S,9R,10R,11S,12S,13R,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-12-yl)-1H-imidazole-1-carbothioate 

Relevant articles and documents

Discovery of a potent steroidal glucocorticoid receptor antagonist with enhanced selectivity against the progesterone and androgen receptors (OP-3633)

Structure-based modification of mifepristone (1) led to the discovery of novel mifepristone derivatives with improved selectivity profile. Addition of a methyl group at the C10 position of the steroid has a significant impact on progesterone receptor (PR) and androgen receptor (AR) activity. Within this series, OP-3633 (15) emerged as a glucocorticoid receptor (GR) antagonist with increased selectivity against PR and AR, improved cytochrome P450 inhibition profile, and significantly improved pharmacokinetic properties compared to 1. Furthermore, 15 demonstrated substantial inhibition of GR transcriptional activity in the GR positive HCC1806 triple negative breast cancer xenograft model. Overall, compound 15 is a promising GR antagonist candidate to clinically evaluate the impact of GR inhibition in reversal or prevention of therapy resistance.

11β-aryl steroids in the androstene series. The role of the 11β-region in steroid progesterone receptor interaction

The syntheses of 11β-arylandrost-4-en-3-one 24 and the corresponding 9β,19-cyclo derivative 8 are described. Steric interaction between C-19 and the aryl residue effects conformational changes of the steroid ring system that result in reduced affinity for the progesterone receptor. The conformation of 11β-arylandrostenes is discussed in comparison with known antiprogestational steroids.