54260-72-9

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium is used as an active pharmaceutical ingredient for the development of new drugs targeting various health conditions. Its unique structure and biological activities make it a promising candidate for the treatment of specific diseases.
Used in Synthesis:
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium is used as a key intermediate in the synthesis of various derivatives with potential applications in the pharmaceutical, chemical, and materials science industries. Its versatile structure allows for further functionalization and modification to create new compounds with tailored properties and improved performance.
Used in Antimicrobial Applications:
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium demonstrates potent antimicrobial activity against a range of bacterial and fungal pathogens. It can be used as an antimicrobial agent in the development of new antibiotics and antifungal drugs to combat drug-resistant infections.
Used in Anti-inflammatory Applications:
Due to its anti-inflammatory properties, 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium can be used in the development of new anti-inflammatory drugs for the treatment of various inflammatory disorders, such as arthritis, asthma, and inflammatory bowel disease.
Used in Antitumor Applications:
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium exhibits antitumor activity, making it a potential candidate for the development of new anticancer drugs. It may be used to target specific cancer cell types and inhibit tumor growth and progression.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic efficacy of 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium, various drug delivery systems can be employed. These systems may include nanoparticles, liposomes, and hydrogels, which can improve the compound's stability, solubility, and targeted delivery to specific tissues or cells.

InChI:InChI=1/C21H20NO4.ClH/c1-12-14-4-5-17(23-2)21(24-3)16(14)10-22-7-6-13-8-18-19(26-11-25-18)9-15(13)20(12)22;/h4-5,8-10H,6-7,11H2,1-3H3;1H/q+1;/p-1

Upstream product

• 633-65-8 berberine chloride 
• 50-00-0 formaldehyd 
• 78-98-8 2-oxopropanal 
• 80665-65-2 9,10-dimethoxy-2,3-methylenedioxy-8,14-cycloberbin-13-one 
• 100986-33-2 9,10-dimethoxy-13-methylene-2,3-methylenedioxy-8,14-cycloberbine 
• 38699-81-9 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 
• 483-15-8 7,8-dihydroberberine 

Relevant academic research and scientific papers

Synthesis method of 13-methyl berberine alkaloid

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 13-methyl berberine alkaloid. The method comprises the following steps: reaction a: taking arylethylamine and aryl formaldehyde as main starting raw materials, and reacting in the presence of other auxiliary materials to obtain secondary amine hydrochloride; and reaction b: taking secondary amine hydrochloride and pyruvic aldehyde as main raw materials, and reacting in the presence of other auxiliary materials to obtain the 13-methyl berberine alkaloid. According to the invention, aryl ethylamine and aryl formaldehyde are used as raw materials to synthesize secondary amine hydrochloride, and then the secondary amine hydrochloride and pyruvic aldehyde are subjected to Pickering-Schengger reaction/Friedel-Crafts hydroxyalkylation reaction/dehydration reaction/oxidation reaction in an anhydrous formic acid solution under the assistance of a dewatering agent and an oxidizing agent, so that the 13-methylberberine alkaloid is prepared at the yield of more than 80%, and the synthesis steps are simplified and easy to operate; and various expensive metal catalysts and excessive acid catalysis are not needed, the productivity is high, and the cost is low.

Synthesis of 13-substituted derivatives of berberine: Aggregation-induced emission enhancement and pH sensitive property

Five kinds of berberine derivatives with hydroxy, methyl, ethyl, benzyl and (4-methyl)benzyl group at 13-position have been synthesized and characterized. 13-hydroxyberberine chloride exhibits aggregation-induced emission enhancement (AIEE) property because of hydroxy group, which is beneficial to increase the rigidity of molecule by enlarging conjugated system. Optical properties in pure solution, CH3OH/H2O mixed solution, amorphous and crystalline state were comparatively investigated. Polymeric morphology and particle size of 13-hydroxyberberine chloride with different water fractions (0–90 vol%) were obtained by scanning electron microscope (SEM) and dynamic light scattering (DLS) method respectively, which provided reasonable explanation that the formation of small globular nanoparticles in mixed solution is conducive to the fluorescence emission. The single crystal structure of 13-hydroxyberberine chloride was determined by single-crystal X-ray diffraction. Crystallographic data indicated that the main mechanism of the AIEE phenomenon is the existences of J-aggregation (head to tail dipole stacking) combined with molecular planarization. The calculation done by DFT showed that the HOMO–LUMO bandgap is in accordance with experimental data. To further explore the biomedical application of 13-hydroxyberberine, its cell viability and cell imaging performance were examined, which demonstrate that 13-hydroxyberberine shows definite fluorescent intensity. In all, 13-hydroxyberberine should be a promising candidate for different biomedical application such as pH fluorescence probe because of its response to the stimuli of pH value.

Berberine compounds and the use of a preparation method

The invention provides application of a compound with the structure as shown in the formula (I) in the specification, or a medical salt, a hydrate or a solvate, of the compound, in preparation of a medicine for treating nervous system diseases relevant to the dopamine receptor, and a preparation method of the compound with the structure as shown in the formula (I) in the specification or the medical salt, the hydrate or the solvate, of the compound. The compound has multiple pharmacologic functions such as mu-opioid receptor excitation and dopamine D2 receptor blocking, and has good physicochemical properties and oral bioavailability, and integral animal experiment shows that the compound has remarkable and long-lasting analgesia and calm activity and can be applied to treatment on pain and other mental diseases.

USE AND PREPARATION METHOD OF BERBERINE COMPOUNDS

A method of treating nervous system diseases associated with dopamine receptors comprising administering a patent in need a compound having a structure of general formula (I) or a pharmaceutical acceptable salt, hydrate, or solvate thereof in a pharmaceutically effective amount, and a method of making the compound having the structure of general formula (I) or a pharmaceutical acceptable salt, hydrate, or solvate thereof. The compound of formula (I) has multiple pharmacological functions such as the functions of activating opioid receptors and blocking dopamine D2 receptors, and has good physicochemical properties and oral bioavailability. General animal experiments show that such a compound has significant and long-lasting analgesic and calming effects and can be used to treat pain and other mental illnesses.

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.

A Novel and Efficient Synthesis of 13-Methylprotoberberine Alkaloids

13-Methylberberine (6a), dehydrocorudaline (6b), and corysamine (6c), and their tetrahydro derivatives (9a-c) were efficiently synthesised from the corresponding protoberberines (1) through photochemical electrocyclic reaction of 13-methylene-8,14-cycloberbines (3).