79133-79-2

Upstream product

• 79133-78-1 2-(4-methoxy-β-phenethyl)-6,7-methylenedioxy-1,2,3,4-tetrahydro-3-isoquinolone 
• 55-81-2 4-Methoxyphenethylamine 
• 1395084-65-7 2-(2H-1,3-benzodioxol-5-yl)-N-[2-(4-methoxyphenyl)ethyl]acetamide 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 72600-39-6 ethyl 2-bromomethyl-4,5-methylenedioxyphenyl acetate 

Relevant academic research and scientific papers

A new class of selective and potent 7-dehydrocholesterol reductase inhibitors

We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC 50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR. Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.

SYNTHESIS OF HETEROCYCLES VIA LACTONES A NEW ROUTE FOR THE SYNTHESIS OF N-β-PHENETHYLTETRAHYDROISOQUINOLINE ALKALOIDS

A convenient synthesis of N-β-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids is described.Condensation of the bromo esters I a-b with β-phenethylamines II a-c afforded the N-β-phenethyl-3-isoquinolones III a-c.Lithium aluminium hydride reduction of th