17388-19-1

Basic information

• Product Name: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol
• Synonyms: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol;5,6-Dihydro-2,3-(methylenedioxy)-9-hydroxy-10-methoxydibenzo[a,g]quinolizinium;5,6-Dihydro-9-hydroxy-10-methoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;9-Berberoline;Berberrubin
• CAS NO: 17388-19-1
• Molecular Formula: C₁₉H₁₆NO₄
• Molecular Weight: 0
• Mol File: 17388-19-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 255-259 °C
• Appearance: /
• CAS DataBase Reference: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol(17388-19-1)
• EPA Substance Registry System: 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol(17388-19-1)

Safety Data

• Hazardous Substances Data: 17388-19-1(Hazardous Substances Data)

Usage

Chemical structure

A quinolizinium derivative with a methoxy group at the 10th position.

Molecular weight

Approximately 357.38 g/mol (calculated from the molecular formula)

Functional groups

Quinolizinium core, methoxy group, benzodioxole ring, and hydroxyl group.

Potential applications

Pharmaceutical and medicinal properties, including possible use in the treatment of neurological disorders or as an analgesic agent.

Research status

Further research and testing are needed to fully understand the potential uses and effects of this chemical compound.

Solubility

Unknown, but may be influenced by the presence of polar functional groups (methoxy and hydroxyl groups).

Stability

Unknown, but the presence of multiple aromatic rings and heteroatoms may contribute to its stability.

Reactivity

Unknown, but the compound may undergo reactions typical of its functional groups, such as nucleophilic substitution or electrophilic aromatic substitution.

Synthesis

The synthesis of this compound is not described in the provided material, but it likely involves the formation of the quinolizinium core, followed by the introduction of the methoxy and hydroxyl groups, and the benzodioxole ring.

InChI:InChI=1/C19H15NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,6-9H,4-5,10H2,1H3/p+1

Upstream product

• 880344-86-5 2-[(2-benzo[1,3]dioxol-5-yl-ethylamino)-methyl]-6-methoxy-phenol 
• 131543-46-9 Glyoxal 
• 2086-83-1 berberine 
• 633-65-8 berberine chloride 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 880344-81-0 2-{[(E)-2-Benzo[1,3]dioxol-5-yl-ethylimino]-methyl}-6-methoxy-phenol 

Relevant articles and documents

Berberrubine attenuates mucosal lesions and inflammation in dextran sodium sulfate-induced colitis in mice

Ulcerative colitis (UC) is a chronic relapsing disease without satisfactory treatments, in which intestinal inflammation and disrupted intestinal epithelial barrier are two main pathogeneses triggering UC. Berberrubine (BB) is deemed as one of the major active metabolite of berberine (BBR), a naturally-occurring isoquinoline alkaloid with appreciable anti-UC effect. This study aimed to comparatively investigate the therapeutic effects of BB and BBR on dextran sodium sulfate (DSS)-induced mouse colitis model, and explore the potential underlying mechanism. Results revealed that BB (20 mg/kg) produced a comparable therapeutic effect as BBR (50 mg/kg) and positive control sulfasalazine (200 mg/kg) by significantly reducing the disease activity index (DAI) with prolonged colon length and increased bodyweight as compared with the DSS group. BB treatment was shown to significantly ameliorate the DSS-induced colonic pathological alternations and decreased histological scores. In addition, BB markedly attenuated colonic inflammation by alleviating inflammatory cell infiltration and inhibiting myeloperoxidase (MPO) and cytokines (TNF-α, IFN-γ, IL-1β, IL-6, IL-4 and IL-10) productions in DSS mice. Furthermore, BB treatment substantially upregulated the expression of tight junction (TJ) proteins (zonula occludens-1, zonula occludens-2, claudin-1, occludin) and mRNA expression of mucins (mucin-1 and mucin-2), and decreased the Bax/Bcl-2 ratio. In summary, BB exerted similar effect to its analogue BBR and positive control in attenuating DSS-induced UC with much lower dosage and similar mechanism. The protective effect observed may be intimately associated with maintaining the integrity of the intestinal mucosal barrier and mitigating intestinal inflammation, which were mediated at least partially, via favorable modulation of TJ proteins and mucins and inhibition of inflammatory mediators productions in the colonic tissue. This is the first report to demonstrate that BB possesses pronounced anti-UC effect similar to BBR and sulfasalazine with much smaller dosage. BB might have the potential to be further developed into a promising therapeutic option in the treatment of UC.

The design and synthesis of a novel compound of berberine and baicalein that inhibits the efficacy of lipid accumulation in 3T3-L1 adipocytes

The combination of berberine and baicalein may have a better therapeutic effect against disease. To explore the combined effect of baicalein and berberine in the treatment of obesity, we designed and synthesized a hybrid compound, and its biological activities were evaluated in 3T3-L1 adipocytes. The structures of the berberine-baicalein (BBS) compounds were confirmed by 1H NMR, 13C NMR, ultraviolet spectroscopy and high resolution mass spectrometry (HRMS). The present study showed that the IC50 values of the inhibitory effects of baicalein, berberine and BBS against 3T3-L1 cells were 29.81 ± 0.90, 21.84 ± 1.67 and 9.42 ± 0.60 μM, respectively. The expression of mRNAs related to lipolysis and lipogenesis were examined by quantitative real-time PCR. The results showed that BBS could up-regulate the expression of the Atgl gene and down-regulate the mRNA expression of Srebp-1c, Fasn, Scd1, and Acc in 3T3-L1 adipocytes. These results indicate that BBS may have a stronger effect than baicalein and berberine on the viability of 3T3-L1 preadipocytes. In addition, BBS may have therapeutic effects and pharmacological activities against obesity. This “medicine couple” may be beneficial for studies of traditional Chinese medicine.

Berberine coupled cis-platinum compound as well as preparation method and application thereof

The invention relates to the technical field of pharmaceutical chemicals, and in particular, relates to a berberine coupled cis-platinum compound as well as a preparation method and application thereof. The invention provides a berberine coupled cis-platinum compound. The berberine coupled cis-platinum compound has a structure represented by a formula I in the specification. Results of the embodiment show that the berberine coupled cis-platinum compound provided by the invention can effectively inhibit the proliferation activity of intestinal cancer cells and significantly reduce the killing ability of cis-platinum to normal intestinal epithelial cells, and in-vivo experiments of mice prove that the berberine coupled cis-platinum compound has a better tumor inhibition effect than cis-platinum.

Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives

Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.