1401939-09-0

Basic information

• Product Name: 3-{(E)-[(13α,16E)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide
• Synonyms: 3-{(E)-[(13α,16E)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide
• CAS NO: 1401939-09-0
• Molecular Weight: 401.505
• Mol File: 1401939-09-0.mol

Chemical Properties

• CAS DataBase Reference: 3-{(E)-[(13α,16E)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-{(E)-[(13α,16E)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide(1401939-09-0)
• EPA Substance Registry System: 3-{(E)-[(13α,16E)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-ylidene]methyl}benzamide(1401939-09-0)

Safety Data

• Hazardous Substances Data: 1401939-09-0(Hazardous Substances Data)

Upstream product

• 53-16-7 (13α)-3-hydroxyestra-1(10),2,4-trien-17-one 
• 126534-87-0 3-carboxamidobenzaldehyde 
• 24964-64-5 3-Cyanobenzaldehyde 

Downstream Products

• 1401939-12-5 3-{[(13α)-3-hydroxy-17-oxoestra-1(10),2,4-trien-16-yl]methyl}benzamide 

Relevant articles and documents

Impact of structural modifications at positions 13, 16 and 17 of 16β-(m-carbamoylbenzyl)-estradiol on 17β-hydroxysteroid dehydrogenase type 1 inhibition and estrogenic activity

The chemical synthesis of four stereoisomers (compounds 5a-d) of 16β-(m-carbamoylbenzyl)-estradiol, a potent reversible inhibitor of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1), and two intermediates (compounds 3a and b) was performed. Assignment of all nuclear magnetic resonance signals confirmed the stereochemistry at positions 13, 16 and 17. Nuclear overhauser effects showed clear correlations supporting a C-ring chair conformation for 5a and b and a C-ring boat conformation for 5c and d. These compounds were tested as 17β-HSD1 inhibitors and to assess their proliferative activity on estrogen-sensitive breast cancer cells (T-47D) and androgen-sensitive prostate cancer cells (LAPC-4). Steroid derivative 5a showed the best inhibitory activity for the transformation of estrone to estradiol (95, 82 and 27%, at 10, 1 and 0.1 μM, respectively), but like the other isomers 5c and d, it was found to be estrogenic. The intermediate 3a, however, was weakly estrogenic at 1 μM, not at all at 0.1 μM, and showed an interesting inhibitory potency on 17β-HSD1 (90, 59 and 22%, at 10, 1 and 0.1 μM, respectively). As expected, no compound showed an androgenic activity. The binding modes for compounds 3a and b, 5a-d and CC-156 were evaluated from molecular modeling. While the non-polar interactions were conserved for all the inhibitors in their binding to 17β-HSD1, differences in polar interactions and in binding conformational energies correlated to the inhibitory potencies.

INHIBITORS OF 17?-HSD1, 17?-HSD3 AND 17?-HSD10

The present application discloses 17β hydroxy steroid dehydrogenase (17β HSD) type 1, 3, 10 inhibitors and use thereof (alone and in combination) in the treatment of cancer and other afflictions. 17β HSDl inhibitors include estradiol derivatives with a ni