2124-26-7

Basic information

• Product Name: (+/-)-20-Aethylendioxy-3α-hydroxy-13α,17α-pregnan
• CAS NO: 2124-26-7
• Molecular Weight: 362.553
• Mol File: 2124-26-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-20-Aethylendioxy-3α-hydroxy-13α,17α-pregnan(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-20-Aethylendioxy-3α-hydroxy-13α,17α-pregnan(2124-26-7)
• EPA Substance Registry System: (+/-)-20-Aethylendioxy-3α-hydroxy-13α,17α-pregnan(2124-26-7)

Safety Data

• Hazardous Substances Data: 2124-26-7(Hazardous Substances Data)

Upstream product

• 145-13-1 Pregnenolone 
• 516-55-2 isopregnanolone 
• 107-21-1 ethylene glycol 

Downstream Products

• 474-45-3 (3α,5α)-3-aminopregnan-20-one 
• 474-45-3 (3β,5α)-3-aminopregnan-20-one 
• 2135-37-7 (3α,5α)-3-aminopregnan-20-one hydrochloride 
• 1373651-62-7 N-[(3β,5α)-20-oxopregnan-3-yl]benzenesulfonamide 

Relevant articles and documents

A- And D-Ring structural modifications of an androsterone derivative inhibiting 17β-hydroxysteroid dehydrogenase type 3: chemical synthesis and structure-activity relationships

Decreasing the intratumoral androgen biosynthesis by using an inhibitor of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) is a strategy to treat prostate cancer. The androsterone (ADT) derivative 1 (RM-532-105) has shown strong inhibitory activity on 17β-HSD3, but needs to be improved. Herein, we describe the chemical synthesis and characterization of two series of analogues to address the impact of A- and D-ring modifications on 17β-HSD3 inhibitory activity, androgenic effect, and metabolic stability. Structure-activity relationships were generated by adding different groups at C16/C17 (D-ring diversification) or replacing the ADT backbone by a nor-androstane or an estrane backbone (A-ring diversification). D-ring derivatives were less potent inhibitors than lead compound 1, whereas steroidal backbone (A-ring) change led to identifying promising novel estrane derivatives. This culminated with potent 17β-HSD3 inhibitors 23, 27, 31, and 33 (IC50 = 0.10, 0.02, 0.13, and 0.17 μM, respectively), which did not stimulate LAPC-4 cell proliferation and displayed higher plasma concentration in mice than lead compound 1.

A novel scalable and stereospecific synthesis of 3α- and 3β-amino-5α-androstan-17-ones and 3α- and 3β-amino- 5α-pregnan-20-ones

A novel scalable stereoselective synthesis of 3α- and 3β-amino-5α-androstan-17-ones and 3α- and 3β-amino- 5α-pregnan-20-ones has been developed using phthalimide based Mitsunobu chemistry. In all four cases, the products were isolated as single diastereoisomers in high chemical yield and purity without the need for chromatography at any stage in their syntheses.