117690-79-6

Usage

Uses

Used in Pharmaceutical Industry:
1-[5-Ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazole-5-yl)heptyl]oxy]phenyl]ethanone is used as a selective, competitive BLT2 receptor antagonist for the treatment of chronic myeloid leukemia. It displaces radiolabeled leukotriene B4 (LTB4) from guinea pig lung membrane, with an IC50 of about 100 nM. 1-[5-ETHYL-2-HYDROXY-4-[[6-METHYL-6-(1H-TETRAZOL-5-YL)HEPTYL]OXY]PHENYL]ETHANONE exhibits IC50 values of ~950 nM and >10 μM at human recombinant BLT2 and BLT1 receptors, respectively. It inhibits eosinophil chemotaxis by 80% at a concentration of 10 μM and inhibits the binding of radiolabeled LTB4 to eosinophil membranes with an IC50 of 260 nM.
Used in Drug Development:
1-[5-Ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazole-5-yl)heptyl]oxy]phenyl]ethanone is used as a potential drug development target for the treatment of chemotactic and inflammatory conditions. Antagonists of LTB4 have been of interest for several years due to their ability to modulate inflammatory responses. The tetrazole group in 1-[5-ETHYL-2-HYDROXY-4-[[6-METHYL-6-(1H-TETRAZOL-5-YL)HEPTYL]OXY]PHENYL]ETHANONE may contribute to its antagonistic properties and selectivity for the BLT2 receptor.
Used in Chemical Research:
1-[5-Ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazole-5-yl)heptyl]oxy]phenyl]ethanone can be used as a starting material or intermediate in the synthesis of other complex organic compounds. Its unique structure and functional groups make it a valuable candidate for further chemical modifications and exploration of its potential applications in various fields, such as materials science, pharmaceuticals, or agrochemicals.

Biological Activity

Selective, competitive antagonist of BLT 2 receptors (IC 50 values are ~ 1 and > 10 μ M at human recombinant BLT 2 and BLT 1 receptors respectively). Inhibits LTB 4 -induced contraction of lung parenchyma (pA 2 = 7.2), and reduces LTB 4 -mediated airway obstruction in guinea pigs following i.v. and oral administration.

InChI:InChI=1/C19H28N4O3/c1-5-14-11-15(13(2)24)16(25)12-17(14)26-10-8-6-7-9-19(3,4)18-20-22-23-21-18/h11-12,25H,5-10H2,1-4H3,(H,20,21,22,23)

Upstream product

• 117690-81-0 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-2,2-dimethylheptanenitrile 
• 17846-68-3 azido tributyltin (IV) 
• 4460-42-8 1-(5-ethyl-2,4-dihydroxyphenyl)ethanone 
• 2896-60-8 4-ethyl-1,3-benzenediol 
• 54512-75-3 1-bromo-5-chloropentane 
• 140660-32-8 2,2-dimethyl-7-chloroheptanenitrile 

Downstream Products

• 140660-20-4 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-2-methyl-2-(2-methyltetrazol-5-yl)heptane 
• 140660-19-1 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-2-methyl-2-(1-methyltetrazol-5-yl)heptane 

Relevant academic research and scientific papers

Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.

Leukotriene B4 Receptor Antagonists: The LY255283 Series of Hydroxyacetophenones

A series of hydroxyacetophenones was prepared for evaluation as leukotriene B4 (LTB4) receptor antagonists, culminating in 1-oxy>phenyl>ethanone (compound 35, LY255283).Using an assay for inhibition of specific LTB4 binding to human PMN, we found that substitution of a nonpolar substituent in the 5-position was required for activity.Best activity was realized with hydrogen in the 3-position, hydroxyl in the 2-position, short chain alkyl ketone in the 1-position, and a six- or eight-carbon chain linking the oxygen in the 4-position with an unsaturated terminal function.Compound 35, having an IC50 of 87 nM in the binding assay, was chosen for further preclinical evaluation.

ANTI-INFLAMMATORY AGENTS

This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.