75608-42-3

Upstream product

• 5487-33-2 O-benzylhomoisovanillic acid 
• 1131-94-8 homoisovanillic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 18028-10-9 N-(3-Benzyloxy-4-methoxy-phenyl)-N-(3,4-dimethoxy-phenaethyl)-acetamid 

Downstream Products

• 53898-95-6 C₁₉H₂₁NO₄ 
• 1395084-83-9 C₂₀H₂₅NO₄ 
• 54370-03-5 5-{2-[2-(3,4-dimethoxyphenyl)ethylamino]ethyl}-2-methoxyphenol 
• 861364-71-8 (3-ethoxycarbonyloxy-4-methoxy-phenyl)-acetic acid-(3,4-dimethoxy-phenethylamide) 

Relevant academic research and scientific papers

COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY

The present technology relates to methods of treating NASH, NAFLD and/or obesity using compounds of Formulas I, II, III, IV, V, and/or VI. The methods include administering to a subject suffering from one or more of non-alcoholic steatohepatitis (NASH), non- alcoholic fatty liver disease (NAFLD) and/or obesity a therapeutically effective amount of such a compound

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.

Biotransformation of phenolic tetrahydroprotoberberines in plant cell cultures followed by LC-NMR, LC-MS, and LC-CD

A metabolic pathway of 2,3,10,11-oxygenated tetrahydroprotoberberines having the OH group on ring D was demonstrated. Metabolism of 13C- or D2-labeled precursors was studied in cell cultures of Macleaya, Corydalis, and Nandina species. The structures of alkaloid metabolites obtained from feeding experiments were determined by application of combined LC-NMR, LC-MS/MS, and LC-CD techniques. (S)-Tetrahydropseudoprotoberberine (5) was stereospecifically O-methylated to the 5-isomer (12) in cell cultures of three plant species. This 5-isomer was further N-methylated to the (5)-α-N-methyl salt (15), which was oxidized to produce the pseudoprotopine-type alkaloid (10) in cell cultures of Macleaya and Corydalis species. These transformations were the same as those of 2,3,9,10-oxygenated protoberberines. The tetrahydropseudoprotoberberines (5, 6, and 12) were dehydrogenated to pseudoprotoberberines (13, 16, and 14), respectively. Both the R- and 5-enantiomers of 5 were dehydrogenated in Macleaya cordata different from the case of 2,3,9,10-oxygenated protoberberines. Precursor 7, with OH groups at C-10 and C-11was O-methylated at C-10 in M. cordata and C. ochotensis var. raddeana, which was distinct from O-methylation in N. domestica, in which 7 was O-methylated at both C-11 and C-10. Stereoselective O-demethylation [(S)-S to (5)-18] occurred in N. domestica.

CORYDALINE DERIVATIVES USEFUL FOR REDUCING LIPID LEVELS

The present technology relates to compounds of Formulas (V) and (VI) and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also lower total cholesterol, LDL- cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated potein kinase.

COMPOUNDS, COMPOSITIONS AND METHODS FOR REDUCING LIPID LEVELS

Compositions comprising extracts or isolated or purified compounds from plants of the genus Corydalis provide prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Corydalis compounds and their derivatives of natural and synthetic origins lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression and activate AMP-activated protein kinase. Specific stereoisomers of Corydalis compounds with lipid lowering activity include 14R-(+)-corypalmine, 14R,13S-(+)-corydaline, 14R-(+)-tetrahydropalmatin, (+)-corlumidin, d-(+)-bicuculline, and (+)-egenine.

Oxidative Coupling of Phenols and Phenolic Ethers. Part 4. Synthesis of Dibenzazonines and a Dibenzazecine, via Direct Coupling

Two series of amides, N-phenethylphenylacetamides (9) and the bisphenetylamides (11), including diphenolic monophenolic, and non-phenolic types, were treated with a range of one-electron oxidants.With the tetramethoxy-derivative (11e) intramolecular coupling yielded a dibenzazonine (16) in 36percent yield.Similar oxidation of the homologue (18) gave a dibenzazecine (19) in 60percent yield.