24997-85-1

Upstream product

• 18034-37-2 N-<2-(3,4-dimethoxybenzyl)ethyl>-3,4-dimethoxybenzaldimine 
• 4230-93-7 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 
• 70360-83-7 1,2-dimethoxy-4-(2-nitroethyl)benzene 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 161988-97-2 (3,4-Dimethoxy-benzyl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-[(Z)-2-((R)-2-nitro-benzenesulfinyl)-vinyl]-amine 
• 55124-87-3 N-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-aminium chloride 
• 523-02-4 (S)-(-)-norcoralydine 
• 31756-19-1 6,7-dimethoxy-2-methyl-2-veratryl-1,2,3,4-tetrahydro-isoquinolinium; iodide 
• 144344-81-0 N-(3,4-dimethoxybenzyl)-N'-formyl-2-(3,4-dimethoxyphenyl)ethanamine 
• 94027-34-6 4,4'-(2-aza-butanediyl)-di-pyrocatechol 
• 96839-24-6 N-(3,4-dimethoxybenzyl)-N'-methyl-2-(3,4-dimethoxyphenyl)ethanamine 
• 91790-53-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline 

Relevant academic research and scientific papers

Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation

A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids, (-)-canadine, (-)-rotundine, (-)-sinactine, and (-)-xylopinine, has been accomplished in three steps from the commercially available corresponding disubstituted phenylethylamine and disubstituted benzaldehyde. Our synthesis toward these four alkaloids took advantage of the following strategy: In the first step, we achieved an efficient and sustainable synthesis of secondary amine hydrochlorides via a fully continuous flow; in the second step, we developed a Pictet-Spengler reaction/Friedel-Crafts hydroxyalkylation/dehydration cascade for the construction of the dihydroprotoberberine core structure (ABCD-ring); and in the last step, Ir-catalyzed enantioselective hydrogenation was employed for the introduction of the desired stereochemistry at the C-14 position in the tetrahydroprotoberberine alkaloids. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as a more diverse set of structurally related non-natural analogues.

Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhanced the survival rate of patient with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives were synthesized and evaluated for their activities on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure–activity relationship (SAR) analysis revealed that 2,3-dimethoxy moiety might be beneficial for activity. Among them, 9k displayed the most potent activity with IC50 value of 9.5 ± 0.5 μM, better than that of BBR. Also, it significantly decreased PCSK9 protein level at cellular level, as well as in the liver and serum of mice in vivo. Furthermore, 9k markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of 9k is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, 9k might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.

Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine

Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been sy

Berberis ALKALOIDS. XXII. INTEBRININE AND INTEBRIMINE - NEW ALKALOIDS FROM Berberis integerrima

The known alkaloids reticuline, isoboldine, isocorydine, glaucine, armepavine, oxyacanthine, and heliamine and the new alkaloids intebrinine and intebrimine have been isolated from the total alkaloids of the leaves of Berberis integerrima, and structures

SYNTHESIS BASED ON &β-PHENYLETHYLAMINES. IV. SYNTHESIS AND ANTIARRHYTHMIC ACTIVITY OF SUBSTITUTED PHENYLALKYLAMINES AND N-BENZYLTETRAHYDROISOQUINOLINES

A number of N-benzyltetrahydroisoquinolines forming analogues of sendaverine have been synthesized.Results on the pharmacological activity of the compounds synthesized are presented.

Ruthenium dioxide in fluoro acid medium. III. Aplication to the synthesis of aporphinic, homoaporphinic and dibenzazocinic alkaloids. Studies towards the preparation of azafluoranthenic skeleton

Intramolecular oxidative couplings of phenylalkyltetrahydroisoquinoline precursors in aporphinic and homoaporphinic alkaloids by using RuO2,2H2O in fluoro acidic media were performed. A comparative study of our reagent with TTFA has been made with different precursors. The procedure was also extended to the synthesis of one dibenzazocinic alkaloid. Then, we attempted to synthetize the azafluoranthenic ring, using phenolic and non phenolic isoquinoline precursors.

A Convenient Synthesis of Apogalanthamine Analogues as α-Adrenergic Blocking Agents using Zerovalent Nickel

The apogalanthamine analogues, 5,6,7,8-tetrahydrodibenzazocine (2) and its N-methyl and N-acetyl derivatives (1 and 3), and the methoxy derivatives (4, 5 and 9) of (1) were obtained in good yields by cyclization of the corresponding halogeno-N-benzyl-β-phenethylamines (10a, 11a-d, 12a,b and 13a-c) using stoichiometric amounts of zerovalent nickel generated in situ and potassium iodide.

N-benzyl-2,2-dimethoxy-acetamides

N-benzyl-2,2-dimethoxy-acetamides having the formula STR1 and processes for preparing the same. These acetamides are useful for the production of 2H-3-isoquinolones by acid cyclization and said 2H-3-isoquinolones are in turn useful as starting materials inter alia in the synthesis of 1,4-dihydro-1,4-etheno-isoquinolin-3(2H)ones, which are valuable chemotherapeutic agents as disclosed in U.S. Pat. No. 3,781,436.