1275575-34-2

Basic information

• Product Name: 5-[3-(N,N-dimethylaminomethyl)-4-hydroxybenzylidene]-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione
• Synonyms: 5-[3-(N,N-dimethylaminomethyl)-4-hydroxybenzylidene]-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione
• CAS NO: 1275575-34-2
• Molecular Weight: 368.389
• Mol File: 1275575-34-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-[3-(N,N-dimethylaminomethyl)-4-hydroxybenzylidene]-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[3-(N,N-dimethylaminomethyl)-4-hydroxybenzylidene]-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione(1275575-34-2)
• EPA Substance Registry System: 5-[3-(N,N-dimethylaminomethyl)-4-hydroxybenzylidene]-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione(1275575-34-2)

Safety Data

• Hazardous Substances Data: 1275575-34-2(Hazardous Substances Data)

Upstream product

• 5416-93-3 4-Methoxyphenyl isocyanate 
• 103260-75-9 3-(4-methoxy-phenyl)-oxazolidine-2,4-dione 
• 116546-04-4 3-<(dimethylamino)methyl>-4-hydroxybenzaldehyde 
• 1275575-33-1 C₁₂H₁₅NO₅ 

Relevant articles and documents

Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors

We have previously reported the discovery of a new class of potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) derived from benzylidene oxazolidinedione and thiazolidinedione scaffolds. In this study, these analogs were designed, synthesized, and evaluated in a human cell-based assay. The detailed structure-activity relationship (SAR) surrounding this pharmacophore were developed, and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg, 16 showed approximately two times more potent testosterone (T)-lowering effect against a positive control in the luteinizing hormone-releasing hormone (LH-RH)-induced T production assay. The T-lowering effect continued at ca 10% level of control over 4 h after administration. The nonsteroidal molecules based on this series have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer.