4880-79-9

Usage

Derivative of

Isoquinoline

Substituents

Four methoxy groups attached to the 2, 3, 9, and 10 positions of the molecule

Ion Present

Iodide ion

Chemical Type

Quaternary ammonium salt

Properties

Pharmaceutical Potential: Due to its unique structure and properties, it has potential pharmaceutical applications.
Organic Synthesis: It may be used in organic synthesis due to its reactivity and functional groups.
Chemical Reagent: It can function as a reagent in various chemical reactions due to its specific molecular structure.

Upstream product

• 2934-97-6 (+/-)-tetrahydropalmatine 
• 74-88-4 methyl iodide 
• 54636-77-0 2,3-dimethoxybenzyl bromide 
• 3893-01-4 2,3-dimethoxybenzyl chloride 
• 75875-52-4 2-(2,3-Dimethoxy-benzyl)-1-(methanesulfinyl-methylsulfanyl-methyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 
• 75875-56-8 2-(2,3-Dimethoxy-benzyl)-1-(methanesulfinyl-methylsulfanyl-methyl)-6,7-dimethoxy-1,2-dihydro-isoquinoline 
• 75875-47-7 2-(2,3-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide 
• 26067-60-7 2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 3520-14-7 (R)-(+)-tetrahydropalmatine 
• 75875-59-1 dihydropalmatine chloride 
• 75875-49-9 6,7-dimethoxy-N-(2,3-dimethoxybenzyl)isoquinolinium chloride 

Downstream Products

• 85547-27-9 8-phenyldihydropalmatine 

Relevant academic research and scientific papers

Berberine analogues as a novel class of the low-density-lipoprotein receptor up-regulators: Synthesis, structure-activity relationships, and cholesterol-lowering efficacy

Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element to keep the activity, (ii) the 7-position quaternary ammonium and planar structure of the compound are activity-required, and (iii) addition of electron-donating groups at the 7- or 13-position reduced the activity. Of the compound 1 analogues, compound 2 exhibited an increased activity on LDLR expression compared to 1.Inthe hyperlipidemic rats, compound 2 (100 (mg/kg)/day) reduced blood CHO and LDL-c by 42.6% and 49.4%, respectively, more efficient than 1 did (p 50 of 2 in mice was over 5000 mg/kg (oral). We consider compound 2 a promising cholesterol- lowering drug candidate.

Chemical Transformation of Protoberberines. VIII. A Novel Synthesis of (+/-)-Fumaricine and a Formal Synthesis of (+/-)-Alpinigenine

Berberine (1) was transformed stereoselectively into either the trans- or cis-hydroxyspirobenzylisoquinoline (9 or 10) via the 8,14-cycloberbine (3).This method was applied to a first transformation of the protoberberine (22) into a spirobenzylisoquinolin

A regiospecific synthesis of protoberberine alkaloids

The protoberberine skeleton has been prepared in two steps from N-benzyl-3,4-dihydroisoquinolinium salts.Treatment of the salts with the anion of methyl methylthiomethylsulfoxide yields mixtures of diastereomeric adducts that cyclize on heating with concentrated hydrochloric acid to dihydroprotoberberines.The latter compounds may be reduced to their tetrahydro analogues with sodium borohydride, oxidized to protoberberinium salts with iodine, or converted to 13-methyltetrahydroprotoberberines by treatment with formaldehyde according to an established procedure.The method has been applied successfully to the synthesis of (+/-)-tetrahydropalmatine, palmatine iodide, (+/-)-xylopinine, (+/-)-sinactine, and (+/-)-corydaline.N-Benzylisoquinolinium salts may be used in place of their dihydro analogues as starting materials in this synthesis, thereby extending the range of substitution patterns potentially available.