6656-19-5

Basic information

• Product Name: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-10,11-dimethoxy-
• CAS NO: 6656-19-5
• Molecular Weight: 339.391
• Mol File: 6656-19-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-10,11-dimethoxy- (CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-10,11-dimethoxy- (6656-19-5)
• EPA Substance Registry System: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-10,11-dimethoxy- (6656-19-5)

Safety Data

• Hazardous Substances Data: 6656-19-5(Hazardous Substances Data)

Upstream product

• 28111-11-7 10,11-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-9-ylamine 
• 19716-54-2 10,11-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-8-one 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 94143-83-6 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 27972-50-5 5-(3,4-dimethoxy-5-nitro-benzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride 
• 47447-28-9 2,3-dimethoxy-5-(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)-aniline 
• 33469-94-2 5-hydroxy-10,11-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium; iodide 
• 116432-77-0 1-benzo[1,3]dioxol-5-yl-2-(3,4-dimethoxy-phenyl)-ethylamine 
• 802899-46-3 3-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 
• 33466-54-5 10,11-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-5-ol 
• 25888-41-9 1-(2-bromo-4,5-dimethoxybenzyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 101481-14-5 5,8,13,14-tetrahydro-12-hydroxy-10,11-dimethoxy-2,3-methylenedioxy-6H-dibenzoquinolizine 
• 73777-77-2 polyberbine 
• 289507-35-3 2-bromo-1-(6-bromobenzo[d][1,3]-dioxol-5-yl)ethan-1-one 

Downstream Products

• 1100757-88-7 2,3-methylenedioxy-10,11-dimethoxy-7-benzyltetrahydroprotoberberine bromide 
• 528-67-6 Fagarin II 

Relevant articles and documents

A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.

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 Protoberbines. XI. A Novel Synthesis of 2,3,10,11-Tetraoxygenated Protoberberine Alkaloids from Corresponding 2,3,9,10-Tetraoxygenated Protoberberine Alkaloids.

2,3,9,10-Tetraoxygenated protoberberin alkaloids, berberine (1a), palmatine (1b), and coptisine (1c) were efficiently converted into the corresponding 12-hydroxy-2,3,10,11-tetraoxygenated protoberberines (6a, 6b, 6c) through an oxidative C8-C8a bond cleav