199592-02-4

Basic information

• Product Name: 5-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)pentanamide
• Synonyms: 5-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)pentanamide
• CAS NO: 199592-02-4
• Molecular Weight: 410.58
• Mol File: 199592-02-4.mol

Chemical Properties

• CAS DataBase Reference: 5-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)pentanamide(199592-02-4)
• EPA Substance Registry System: 5-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)pentanamide(199592-02-4)

Safety Data

• Hazardous Substances Data: 199592-02-4(Hazardous Substances Data)

Upstream product

• 24544-04-5 2,6-diisopropylbenzenamine 
• 2067-33-6 5-bromopentanoic acid 
• 199592-71-7 5-bromo-N-(2,6-diisopropylphenyl)pentanamide 
• 2382-96-9 2-sulfanyl-1,3-benzoxazole 

Relevant articles and documents

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

Anilide compounds, including use thereof in ACAT inhibitition

The invention provides novel anilide compounds and pharmaceutical compositions comprising them. The invention relates to compounds of a formula: where Ar is an optionally-substituted aryl group; R4and R5are the same or different, and each is a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and R4and R5may together form a lower alkylene group of which one or more methylene moieties may optionally be substituted by oxygen and/or sulfur atoms; X is —NH—, or oxygen or sulfur atom; Y is —NH—, an oxygen or sulfur atom, or a sulfoxide or sulfone group; Z is a single bond, or —NH6—; R6represents a hydrogen atom or a lower alkylene group; and n is an integer of from 0 to 15; and their salts and solvates. The compounds of the invention are useful as pharmaceutical compositions, especially as acyl coenzyme A cholesterol acyltransferase (ACAT) inhibitors.