1401937-83-4

Basic information

• Product Name: 3-{[(16β,17β)-3-amino-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide
• Synonyms: 3-{[(16β,17β)-3-amino-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide
• CAS NO: 1401937-83-4
• Molecular Weight: 404.552
• Mol File: 1401937-83-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-{[(16β,17β)-3-amino-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-{[(16β,17β)-3-amino-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide(1401937-83-4)
• EPA Substance Registry System: 3-{[(16β,17β)-3-amino-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide(1401937-83-4)

Safety Data

• Hazardous Substances Data: 1401937-83-4(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 1401938-26-8 3-{(E)-[(16E,17β)-3-amino-17-hydroxyestra-1,3,5(10)trien-16-ylidene]methyl}benzamide 
• 1401938-25-7 3-{(E)-[(16E)-3-amino-17-oxoestra-1,3,5⁽¹⁰⁾trien-16-ylidene]methyl}benzamide 
• 126534-87-0 3-carboxamidobenzaldehyde 
• 18119-98-7 (3aS,3bR,9bS,11aS)‐7‐amino‐11a‐methyl‐1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren‐1‐one 

Relevant articles and documents

Discovery of a non-estrogenic irreversible inhibitor of 17β-Hydroxysteroid dehydrogenase type 1 from 3-substituted-16β-(m -carbamoylbenzyl)-estradiol derivatives

17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) is thought to play a pivotal role in the progression of estrogen-sensitive breast cancer by transforming estrone (E1) into estradiol (E2). We designed three successive series of E2-derivatives at position C3 of the potent inhibitor 16β-(m-carbamoylbenzyl)-E2 to remove its unwanted estrogenic activity. We report the chemical synthesis and characterization of 20 new E2-derivatives, their evaluation as 17β-HSD1 inhibitors, and their proliferative (estrogenic) activity on estrogen-sensitive cells. The structure-activity relationship study provided a new potent and steroidal nonestrogenic inhibitor of 17β-HSD1 named 3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra- 1(10),2,4-trien-16-yl]methyl}benzamide (23b). In fact, this compound inhibited the transformation of E1 into E2 by 17β-HSD1 in T-47D cells (IC 50 = 83 nM), did not inhibit 17β-HSD2, 17β-HSD7, 17β-HSD12, and CYP3A4, and did not stimulate the proliferation of estrogen-sensitive MCF-7 cells. We also discussed the results of kinetic and molecular modeling (docking) experiments, suggesting that compound 23b is a competitive and irreversible inhibitor of 17β-HSD1.