475-81-0

Usage

Uses

Used in Pharmaceutical Industry:
BOLDINE DIMETHYL ETHER is used as a pharmaceutical agent for its potential therapeutic effects. It is being investigated for its anti-inflammatory properties, which may help in the treatment of various inflammatory conditions. Additionally, its antitumor activity suggests potential use in cancer therapy, particularly in targeting specific cancer cells and pathways.
Used in Cosmetic Industry:
Due to its potential anti-inflammatory and antitumor properties, BOLDINE DIMETHYL ETHER may also find applications in the cosmetic industry. It could be incorporated into skincare products to provide anti-aging and skin health benefits, as well as to promote a healthy skin barrier.
Used in Research and Development:
BOLDINE DIMETHYL ETHER is used as a research compound for studying its biological activities and potential applications in various fields. Its unique structure and properties make it an interesting candidate for further investigation into its therapeutic potential and possible uses in drug development.

InChI:InChI=1/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1

Upstream product

• 5630-11-5 (+/-)-glaucine 
• 186581-53-3 diazomethane 
• 1699-51-0 laudanosine 
• 476-70-0 boldine 
• 1336-21-6 ammonium hydroxide 
• 7732-18-5 water 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 371196-15-5 N-formyl-laurolitsine 
• 67-56-1 methanol 
• 22185-91-7 2-(2-Bromo-4,5-dimethoxyphenyl)-N-<2-(3,4-dimethoxyphenyl)-ethyl>-acetamide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 41823-67-0 1-(2'-bromo-4',5'-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 4230-93-7 3,4-dimethoxynitrostyrene 

Downstream Products

• 3019-51-0 isoboldine 
• 25651-04-1 bracteoline 
• 1418137-71-9 11-sulfonyl-1,11-anhydrobracteoline 
• 5083-88-5 thaliporphine 
• 21848-62-4 1,2,9,10-tetramethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 72498-23-8 glaucine N-oxide 
• 20068-96-6 (+)-thalicmidine 

Relevant academic research and scientific papers

In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT2 and α1 receptors

Compounds with activity at serotonin (5-hydroxytryptamine) 5-HT2 and α1 adrenergic receptors have potential for the treatment of central nervous system disorders, drug addiction or overdose. Isolaureline, dicentrine and glaucine enantiomers were synthesized, and their in vitro functional activities at human 5-HT2 and adrenergic α1 receptor subtypes were evaluated. The enantiomers of isolaureline and dicentrine acted as antagonists at 5-HT2 and α1 receptors with (R)-isolaureline showing the greatest potency (pKb?=?8.14 at the 5-HT2C receptor). Both (R)- and (S)-glaucine also antagonized α1 receptors, but they behaved very differently to the other compounds at 5-HT2 receptors: (S)-glaucine acted as a partial agonist at all three 5-HT2 receptor subtypes, whereas (R)-glaucine appeared to act as a positive allosteric modulator at the 5-HT2A receptor.

Enantioselective synthesis and anti-parasitic properties of aporphine natural products

Chagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents.

Semisynthetic studies on and biological evaluation of N-methyllaurotetanine analogues as ligands for 5-HT receptors

N-Methyllaurotetanine (1) has been reported to display good affinity for the 5-HT1A receptor, but no structure-affinity studies have been performed to date. The commercially available alkaloid boldine (2) was used as the starting material for s

Semisynthesis and myocardial activity of thaliporphine N-homologues

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats

The antihyperglycemic actions of some aporphines and their derivatives in normal Wistar, streptozotocin (STZ)-induced diabetic (IDDM) and nicotinamide-STZ induced diabetic (NIDDM) rats were investigated in this study. These compounds included thaliporphine, glaucine, boldine, N-methyllaurotetanine, and predicentrine and the derivatives, N-[2-(2-methoxyphenoxy)ethyl]-norglaucine and diacetyl-N-allylsecoboldine. Bolus intravenous injection of these compounds decreased the plasma glucose levels in a dose-dependent manner in both normal and diabetic rats. Among them, thaliporphine was found to have the most potent antihyperglycemic effect in both NIDDM and IDDM diabetic rats. It was found that thaliporphine could stimulate the release of insulin in both normal and diabetic rats, and a dose of 1 mg per kg thaliporphine could significantly attenuate the increase of plasma glucose induced by an intravenous glucose challenge test in normal rats. Similar treatment with thaliporphine significantly increased the skeletal muscle glycogen synthesis in both normal and diabetic rats. Hence, the hypoglycemic effect of thaliporphine in diabetic rats could be attributed to the stimulation of insulin release and the increase of glucose utilization. Georg Thieme Verlag KG Stuttgart.

Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: Halogenation and D1 receptor selectivity

Halogenation of the aporphine alkaloid boldine at the 3-position leads to increased affinity for rat brain D1-like dopaminergic receptors with some selectivity over D2-like receptors. A series of 3-halogenated and 3,8-dihalogenated (halogen = Cl, Br or I) derivatives of predicentrine (9-O-methylboldine) and glaucine (2,9-di-O-methylboldine) were prepared and assayed for binding at D1 and D2 sites. Halogenation of predicentrine led to strong increases in affinity for D1-like receptors, while the affinities for D2-like receptors were either practically unchanged or reduced three- to fourfold. Halogenated glaucine derivatives did not show any clear trend towards enhanced selectivity, and the affinities were poor and similar to or worse than the values previously recorded for glaucine itself. Together with earlier work on boldine derivatives, these results suggest that the 2-hydroxy group on the aporphine skeleton may determine a binding mode favoring D1-like over D2-like receptors, with enhanced affinity when the C-3 position is halogenated.

Stereoselective synthesis of aporphine alkaloids using a hypervalent iodine(III) reagent-promoted oxidative nonphenolic biaryl coupling reaction. Total synthesis of (S)-(+)-glaucine

The aporphine alkaloid (+)-glaucine (8a) and two other analogues 8b,c have been synthesized in good yield and high ee from the appropriate 1,2-diarylethylamine derivatives, which were in turn prepared using (S)-(+)-phenylglycinol as chiral support. Next, a sequence of simple transformations: N-alkylation with bromoacetaldehyde diethyl acetal, N-methylation, Pommeranz-Fritsch cyclization, and ionic hydrogenation led to the key intermediate, optically active, 1-benzyltetrahydroisoquinolines 7a-c. The final C-ring closure step was performed by C-C biaryl bond formation by an hypervalent iodine(III) reagent promoted oxidative coupling, affording the target heterocycles 8a-c in good yields and with no racemization at the formerly created stereogenic center.

A facile method for the synthesis of glaucine and norglaucine from boldine

A large-scale preparation of glaucine was achieved by reacting boldine with trimethylphenylammonium chloride and potassium t-butoxide in high yield. Treatment of glaucine with 30% H202, subsequent with hydrated ferrous sulfate, afforded norglaucine in an overall yield of 40%.

Chiral auxiliary mediated pictet-spengler reactions: Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine

Cyclohexyl-based chiral auxiliaries can be used effectively in an asymmetric Pictet-Spengler synthesis of tetrahydroisoquinoline, aporphine and protoberbine alkaloids. Using this strategy, concise asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (+)- xylopinine have been accomplished.

Enantioselective synthesis of (R)-(-)-laudanosine and (R)-(-)-glaucine from L-ascorbic acid

L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine.