204589-94-6

Basic information

• Product Name: 5-(4-fluorophenyl)-3-pentenoic acid
• Synonyms: 5-(4-fluorophenyl)-3-pentenoic acid
• CAS NO: 204589-94-6
• Molecular Weight: 194.206
• Mol File: 204589-94-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-(4-fluorophenyl)-3-pentenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-fluorophenyl)-3-pentenoic acid(204589-94-6)
• EPA Substance Registry System: 5-(4-fluorophenyl)-3-pentenoic acid(204589-94-6)

Safety Data

• Hazardous Substances Data: 204589-94-6(Hazardous Substances Data)

Upstream product

• 405-69-6 (E,Z)-1-(buta-1,3-dien-1-yl)-4-fluorobenzene 
• 124-38-9 carbon dioxide 
• 591-80-0 pent-4-enoic acid 
• 352-34-1 4-fluoro-1-iodobenzene 

Downstream Products

• 24484-22-8 5-(4-fluorophenyl)-pentanoic acid 
• 204589-96-8 (3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-propyl]-azetidin-2-one 
• 204589-58-2 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)propyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone 
• 204589-92-4 5-(4-fluorophenyl)pentanoyl chloride 

Relevant articles and documents

Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)- hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption

(3R)-(3-Phenylpropyl)-1,(4S)-bis(4-methoxyphenyl)-2-azetidinone (2, SCH 48461), a novel inhibitor of intestinal cholesterol absorption, has recently been described by Burnett et al. and has been demonstrated to lower total plasma cholesterol in man. The potential sites of metabolism of 2 were considered, and the most probable metabolites were prepared. The oral cholesterol-lowering efficacy of the putative metabolites was evaluated in a 7-day cholesterol-fed hamster model for the reduction of serum total cholesterol and liver cholesteryl esters versus control. On the basis of our analysis of the putative metabolite structure-activity relationship (SAR), SCH 58235 (1, 1-4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]- (4S)-(4-hydroxyphenyl)-2-azetidinone) was designed to exploit activity enhancing oxidation and to block sites of potential detrimental metabolic oxidation. Additionally, a series of congeners of 2 were prepared incorporating strategically placed hydroxyl groups and fluorine atoms to further probe the SAR of 2-azetidinone cholesterol absorption inhibitors. Through the SAR analysis of a series of putative metabolites of 2, compound 1 was targeted and found to exhibit remarkable efficacy with an ED50 of 0.04 mg/kg/day for the reduction of liver cholesteryl esters in a 7-day cholesterol-fed hamster model.

Synthesis of 3-arylpropenyl, 3-arylpropynyl and 3-arylpropyl 2-azetidinones as cholesterol absorption inhibitors: Application of the palladium-catalyzed arylation of alkenes and alkynes

A series of 3-(3'-arylpropenyl)-2-azetidinones 8a-8k and 3-(3'-arylpropynyl)-2-azetidinones 16m-16p were prepared by the palladium-catalyzed arylation of 3-(3'-propenyl)-2-azetidinone 7, or by arylation of 4-pentenoic acid, or via ethyl 4-pentynoate followed by 2-azetidinone ring construction. The unsaturated 2-azetidinones were transformed to their saturated analogs 9a-9p by catalytic hydrogenation. Azetidinones 8a-8k, 9a-9p, and 16m-16p were evaluated for their biological activity as cholesterol absorption inhibitors in hamsters. (C) 2000 Elsevier Science Ltd.