179420-67-8

Basic information

• Product Name: 4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl
• Synonyms: 4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl;WSNKLYIWJLWVDJ-UHFFFAOYSA-N
• CAS NO: 179420-67-8
• Molecular Formula: C₁₄H₁₇FO₄
• Molecular Weight: 268.2807832
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 179420-67-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl(179420-67-8)
• EPA Substance Registry System: 4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl(179420-67-8)

Safety Data

• Hazardous Substances Data: 179420-67-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl is used as an intermediate in the synthesis of an imidazole 5-lipoxygenase (5-LO) inhibitor. The compound plays a crucial role in the development of this inhibitor, which is designed to target and inhibit the 5-LO enzyme, a key player in the production of inflammatory mediators such as leukotrienes. By inhibiting this enzyme, the compound can potentially contribute to the treatment of various inflammatory conditions, including asthma and other allergic diseases.

Upstream product

• 179420-66-7 ethyl 4-(5-benzyloxy-3-fluorophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate 
• 461-96-1 3,5-difluorobromobenzene 
• 179420-62-3 Ethyl 1-(3-benzyloxy-5-fluorophenyl)cyclopentane-1-carboxylate 
• 179420-64-5 diethyl 5-benzyloxy-3-fluorophenylmalonate 
• 179420-65-6 ethyl 3-benzyloxy-5-fluorophenylacetate 
• 130722-44-0 5-benzyloxy-3-fluorophenyl bromide 

Downstream Products

• 179420-11-2 ethyl 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate 
• 179420-13-4 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylic acid 
• 179420-14-5 4-(3-fluoro-5-{[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy}phenyl)tetrahydro-2H-pyran-4-carboxamide 

Relevant articles and documents

TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE

Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.

Efficient synthesis of 4-(3-fluoro-5-{[4-(2-methyl-1h-imidazol-1-yl)benzyl] -oxy}phenyl)tetrahydro-2h-pyran-4-carboxamide, a novel 5-lipoxygenase inhibitor

An efficient synthesis of 1, a novel orally active 5-lipoxygenase inhibitor, was developed. Key features of the modified synthetic route include facile construction of the benzyl phenyl ether moiety by nucleophilic aromatic substitution and THP ring by cyclization, and base-promoted hydrolysis of the nitrile group to carboxamide. The improved three-step synthesis provides 25 g of 1 for pre-clinical toxicology studies in a total yield of 59%.

4-[5-Fluoro-3-[4-(2-methyl-1H-imidazol-1-yl)benzyloxy]phenyl]-3,4,5, 6-tetrahydro-2H-pyran-4-carboxamide, an Orally Active Inhibitor of 5-Lipoxygenase with Improved Pharmacokinetic and Toxicology Characteristics

Described herein are structure- activity relationships (SARs) of 4-[5-fluoro-3-[4-(2-methyl-1H-imidazol-1-yl)benzyloxy]-phenyl]-4-methoxy-3,4,5, 6-tetrahydro-2H-pyran (1, CJ-12,918), an imidazole 5-lipoxygenase (5-LO) inhibitor. When 1 was tested in precl

5-lipoxygenase inhibitors

Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having the following formula I: STR1 and the pharmaceutically acceptable salts thereof, wherein Ar1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, py