1379032-22-0

Basic information

• Product Name: 5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
• Synonyms: 5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
• CAS NO: 1379032-22-0
• Molecular Weight: 379.796
• Mol File: 1379032-22-0.mol

Chemical Properties

• CAS DataBase Reference: 5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one(1379032-22-0)
• EPA Substance Registry System: 5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one(1379032-22-0)

Safety Data

• Hazardous Substances Data: 1379032-22-0(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 870704-13-5 3-chloro-5-fluoro-4-hydroxybenzaldehyde 
• 1275575-52-4 C₁₀H₉NO₃S 

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.