114289-47-3

Usage

Uses

Used in Pharmaceutical Industry:
2,2-DIMETHYL-N-(2,4,6-TRIMETHOXYPHENYL)DODECANAMIDE is used as an ACAT-1 inhibitor for the treatment of hypercholesterolemia. It helps in reducing the levels of plasma total cholesterol, VLDL cholesterol, LDL cholesterol, apolipoprotein B, liver cholesteryl esters, and VLDL and LDL cholesteryl ester content, thereby decreasing the risk of atherosclerosis and other cardiovascular diseases.
Used in Research Applications:
2,2-DIMETHYL-N-(2,4,6-TRIMETHOXYPHENYL)DODECANAMIDE is used as a research tool to study its anti-hepatitis C virus (HCV) activity in Huh7.5.1 cells, to treat Neuro-2a cells to test its effect on plasma membrane integrated density of α4-SEPβ2 or α6-SEPβ2β3 nicotinic acetylcholine receptors (nAChRs), and to investigate its effects on the anti-angiogenic activity of pyripyropenes in human umbilical vein endothelial cells. These applications help researchers understand the potential therapeutic effects of CI-976 in various diseases and conditions.

Biological Activity

Selective acyl-coenzyme A:cholesterol acyltransferase (ACAT) inhibitor (IC 50 = 0.073 μ M). Lowers non-high density lipoprotein (HDL)-cholesterol and increases HDL-cholesterol concentrations in rats with pre-established dyslipidaemia. Orally active.

Biochem/physiol Actions

CI-976, a new trimethoxy fatty acid anilide, is a potent and specific inhibitor of liver and intestinal acyl coenzyme A; cholesterol acyltransferase (ACAT) in vitro. CI-976 decreased non-high density lipoprotein (HDL)-cholesterol and increased HDL-cholesterol in rats with pre-established dyslipidemia. High performance gel chromatographic separation of plasma lipoproteins also revealed that CI-976, but not CL 277,082, lowered low density lipoprotein (LDL)-cholesterol and elevated HDL-cholesterol.

InChI:InChI=1/C23H39NO4/c1-7-8-9-10-11-12-13-14-15-23(2,3)22(25)24-21-19(27-5)16-18(26-4)17-20(21)28-6/h16-17H,7-15H2,1-6H3,(H,24,25)

Upstream product

• 112-29-8 1-bromo dodecane 
• 2874-73-9 2,2-Dimethyl dodecanoic acid 
• 60631-34-7 2,2-dimethyldodecanoyl chloride 
• 102438-99-3 2,4,6-trimethoxyaniline hydrochloride 

Relevant academic research and scientific papers

Inhibitors of Acyl-CoA:cholesterol acyltransferase. I. Identification and structure-activity relationships of a novel series of fatty acid anilide hypocholesterolemic agents

A series of fatty acid anilides was prepared, and compounds were tested for their ability to inhibit the enzyme acyl-CoA:cholesterol acyltransferase (ACAT) in vitro and to lower plasma total cholesterol and elevate high- density lipoprotein cholesterol in cholesterol-fed rats in vivo. The compounds reported were found to fall into two subclasses with different anilide SAR. For nonbranched acyl analogues, inhibitory potency was found to be optimal with bulky 2,6-dialkyl substitution. For α-substituted acyl analogues, there was little dependence of in vitro potency on anilide substitution and 2,4,6-trimethoxy was uniquely preferred. Most of the potent inhibitors (IC50 50 nM) were found to produce significant reductions in plasma total cholesterol in cholesterol-fed rats. Additionally, in vivo activity could be improved significantly by the introduction of α,α- disubstitution into the fatty acid portion of the molecule. A narrow group of α,α-disubstituted trimethoxyanilides, exemplified by 2,2-dimethyl-N-(2,4,6- trimethoxyphenyl)dodecanamide (39), was found to not only lower plasma total cholesterol (-60%) in cholesterol-fed rats but also elevate levels of high- density lipoprotein cholesterol (+94%) in this model at the screening dose of 0.05% in the diet (ca. 50 mg/kg).

Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase

Certain substituted amides of saturated fatty acids are potent inhibitors of the enzyme acyl-CoA:cholesterol acyltransferase and are thus useful agents for inhibiting the intestinal absorption of cholesterol.