5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride

Base Information

• Chemical Name: 5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride
• CAS No.: 54260-72-9
• Molecular Formula: C21H20 N O4 . Cl
• Molecular Weight: 385.847
• NSC Number: 299531
• DSSTox Substance ID: DTXSID70969276
• ChEMBL ID: CHEMBL462141
• Mol file: 54260-72-9.mol

Synonyms:54260-72-9;13-Methylberberine;13-Methylberberine chloride;5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride;13-Methylberberine (chloride);16,17-dimethoxy-21-methyl-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride;5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium;13-Methylberberinium chloride;CHEMBL462141;DTXSID70969276;NSC299531;AKOS037515271;NSC 299531;NSC-299531;Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride;MS-26364;PD057725;HY-125827;CS-0032496;E87129;9,10-Dimethoxy-13-methyl-5,6-dihydro-2H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride

Chemical Property of 5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride

Chemical Property:

• Melting Point: 198-200 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 40.80000
• Density: g/cm³
• LogP: 0.40870
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 385.1080858
• Heavy Atom Count: 27
• Complexity: 516

Purity/Quality:

≥98% ^*data from raw suppliers

13-Methylberberine (chloride) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC(=C(C2=C[N+]3=C1C4=CC5=C(C=C4CC3)OCO5)OC)OC.[Cl-]
• Description: 13-Methylberberine (13-MB) (chloride) is a 13-methyl-substituted derivative of berberine . Berberine is a widely distributed berberidaceaen alkaloid found in plant tissues that has antibacterial, anti-inflammatory, antitumor, anti-obesity, and hypercholesterolemic activity. 13-MB has improved antibacterial activity against S. aureus (MIC = 125 μg/ml) and improved antitumor activity with a mean GI50 value of 11.7 μM, as compared to berberine. 13-MB also induces down-regulation of adipocyte differentiation transcription factors, reduces de novo lipid synthesis, and accumulates in murine 3T3-L1 adipocytes at higher levels than berberine, suggesting improved anti-obesity activity.
• Uses: 13-Methylberberinium Chloride can be used to treat and prevent immunoinflammatory dermal disorders. It can also be used in synthesis to result in derivatives that can be used to treat nerve diseases and anti-infective agents.

Technology Process of 5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride

There total 8 articles about 5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 7,8-dihydroberberine (483-15-8) → 2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine chloride (54260-72-9)

Guidance literature:

formaldehyd; 7,8-dihydroberberine; With acetic acid; In ethanol; water; at 85 - 95 ℃; for 5h;

With hydrogenchloride; In water; at 20 ℃; for 1h;

Reference yield: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + berberine chloride (633-65-8) → 2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine chloride (54260-72-9)

Guidance literature:

berberine chloride; With potassium carbonate; sodium hydroxide; In methanol; at 20 ℃; for 1h;

formaldehyd; With acetic acid; In ethanol; water; at 85 - 95 ℃;

Reference yield: 87.0%

2-(3,4-methylenedioxyphenyl)-N-(2,3-dimethoxybenzyl)ethylamine hydrochloride + 2-oxopropanal (78-98-8) → 2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine chloride (54260-72-9)

Guidance literature:

2-oxopropanal; With formic acid; magnesium(II) sulfate; In water monomer; at 60 ℃; for 0.5h; Sealed tube;

N-(2',3-dimethoxybenzyl)-3,4-methylenedioxyphenethylamine hydrochloride; With iodine; at 100 ℃; Sealed tube;

With hydrogenchloride; In water monomer;

upstream raw materials:

formaldehyd

7,8-dihydroberberine

9,10-dimethoxy-13ξ-methyl-5,6,8,13-tetrahydro-8r,13ac-propano-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-16-one

9,10-dimethoxy-13-methylene-2,3-methylenedioxy-8,14-cycloberbine

Refernces

13-(2-methylbenzyl) berberine is a more potent inhibitor of MexXY-dependent aminoglycoside resistance than berberine

10.3390/antibiotics8040212

The research focused on synthesizing berberine derivatives to inhibit MexXY-dependent aminoglycoside resistance in Pseudomonas aeruginosa. The study synthesized 11 berberine derivatives and tested their inhibitory activities against MexXY in both MexXY-positive and MexXY-negative P. aeruginosa strains. The most potent derivative, 13-(2-methylbenzyl) berberine (13-o-MBB), was found to reduce the minimum inhibitory concentrations (MICs) of various aminoglycosides significantly in a multidrug-resistant P. aeruginosa strain. Experiments involved assessing MICs, determining fractional inhibitory concentration (FIC) indices to evaluate synergistic effects, and conducting time-kill assays to measure bactericidal activity. The analyses included NMR and mass spectrometry for compound characterization and CLSI standards for categorizing antibiotic susceptibility. The study concluded that 13-o-MBB is a more potent inhibitor of MexXY-dependent aminoglycoside resistance than berberine, offering a promising approach to overcoming antibiotic resistance in P. aeruginosa.

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