2139-43-7

Usage

Uses

Used in Organic Synthesis:
5-BROMO-6-[1,3]DIOXOLAN-2-YL-BENZO[1,3]DIOXOLE is used as a key intermediate in organic synthesis for the creation of various chemical compounds. Its unique structure allows for versatile reactions and modifications, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-BROMO-6-[1,3]DIOXOLAN-2-YL-BENZO[1,3]DIOXOLE is utilized as a building block in the development of new molecules with potential medicinal uses. Its distinctive properties and reactivity enable the design and synthesis of novel drug candidates, contributing to the advancement of drug discovery and therapeutic innovation.
Used in Biological Process Studies:
5-BROMO-6-[1,3]DIOXOLAN-2-YL-BENZO[1,3]DIOXOLE's unique structure and properties make it a valuable tool in the study of biological processes. Researchers can use 5-BROMO-6-[1,3]DIOXOLAN-2-YL-BENZO[1,3]DIOXOLE to investigate its interactions with biological systems, potentially leading to a better understanding of molecular mechanisms and the development of targeted therapies.
Used in Drug Discovery:
As a component in drug discovery, 5-BROMO-6-[1,3]DIOXOLAN-2-YL-BENZO[1,3]DIOXOLE plays a significant role in the identification and optimization of new drug candidates. Its unique chemical properties allow for the exploration of novel molecular scaffolds and the development of innovative therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C10H9BrO4/c11-7-4-9-8(14-5-15-9)3-6(7)10-12-1-2-13-10/h3-4,10H,1-2,5H2

Upstream product

• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 107-21-1 ethylene glycol 
• 994-30-9 triethylsilyl chloride 
• 120-57-0 piperonal 

Downstream Products

• 42202-83-5 α-2-<(1,3-dioxolan-2-yl)-4,5-methylenedioxyphenyl>-3,4,5-trimethoxybenzyl alcohol 
• 116171-63-2 methyl (E)-3,4-dimethoxy-2'-formyl-4',5'-methylenedioxystilbene-2-carboxylate 
• 132628-85-4 methyl (E)-3,4-dimethoxy-2'-(1,3-dioxolan-2-yl)-4',5'-methylenedioxystilbene-2-carboxylate 
• 116171-69-8 methyl 2-(2-methoxycarbonyl-3,4-dimethoxyphenyl)-7,8-methylenedioxy-1H-3-benzazepine-4-carboxylate 
• 116171-65-4 methyl (3,4-dimethoxyphenyl)-1-(2-methoxycarbonyl-6,7-methylenedioxy)-isoquinoline-3-carboxylate 
• 116171-64-3 methyl (E)-2'-(2-azido-2-methoxycarbonylvinyl)-3,4-dimethoxy-4',5'-methylenedioxystilbene-2-carboxylate 
• 179936-98-2 (+/-)-5-(1,3-dioxolanyl)-[6-(1-hydroxy-3-phenylpropyl)]-1,3-benzodioxole 
• 1379669-24-5 5-[methoxy(3,4,5-trimethoxyphenyl)methyl]-6-[1,3]dioxolan-2-ylbenzo[1,3]dioxole 
• 1379669-25-6 5-[naphth-2-ylmethoxy(3,4,5-trimethoxyphenyl)methyl]-6-[1,3]dioxolan-2-ylbenzo[1,3]dioxole 
• 1379669-30-3 1,4-bis{([1-(3,4,5-trimethoxyphenyl)]-{1-[1-(1,3-dioxolanyl)-4,5-(methylene-1,3-dioxy)]phenyl}methyl)}benzene 
• 1379669-35-8 6-[(naphth-2-ylmethoxy)-(3,4,5-trimethoxyphenyl)methyl]-benzo[1,3]dioxole-5-carbaldehyde 

Relevant academic research and scientific papers

Palladium-catalyzed annulation of arynes by 2-halobenzaldehydes: Synthesis of fluoren-9-ones

(Chemical Equation Presented) Arynes, generated in situ from 2-(trimethylsilyl)aryl triflates and CsF, undergo annulation by o-haloarenecarboxaldehydes in the presence of a Pd catalyst, providing a useful new method for the synthesis of fluoren-9-ones in good yields.

The effect of carbonyl on the isomerization of a galanthan ring system and total synthesis of (±)-β-lycorane

Lycorine-type alkaloids are privileged structures in drug development due to their attractive biological activities. In this paper, the carbonyl on the C ring was proved to have played a critical role in stereoselectivity during the synthesis process, and the galanthan skeleton with acis-B/C ring is more thermodynamically stable in its presence. Furthermore, the total synthesis of (±)-β-lycorane was successfully completed by employing the Michael addition reaction to construct the galanthan skeleton with atrans-B/C ring. This system might be applied to other structural types with similar stereochemistry setting.

Copper-Catalyzed Tandem Cross-Coupling and Alkynylogous Aldol Reaction: Access to Chiral Exocyclic α-Allenols

An enantioselective copper-catalyzed tandem cross-coupling/alkynylogous aldol reaction has been developed. The tetrasubstituted allenoates containing both central and axial chirality have been obtained in moderate to good yields and excellent enantio-and

Short, enantioselective, gram-scale synthesis of (?)-zephyranthine

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (?)-zephyranthine. The concise route includes a catalytic Micha

COMPOUNDS FOR THE INHIBITION OF UNREGULATED CELL GROWTH

The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly cancer stem cells. Particularly, the invention relates to compounds of Formula I to XXII for the treatment of cancer.

Structure-Activity Relationship Study Enables the Discovery of a Novel Berberine Analogue as the RXRα Activator to Inhibit Colon Cancer

We reported recently that berberine (Ber), a traditional oriental medicine to treat gastroenteritis, binds and activates retinoid X receptor α (RXRα) for suppressing the growth of colon cancer cells. Here, we extended our studies based on the binding mode of Ber with RXRα by design, synthesis, and biological evaluation of a focused library of 15 novel Ber analogues. Among them, 3,9-dimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride (B-12) was identified as the optimal RXRα activator. More efficiently than Ber, B-12 bound and altered the conformation of RXRα/LBD, thereby suppressing the Wnt/β-catenin pathway and colon cancer cell growth via RXRα mediation. In addition, B-12 not only preserved Ber's tumor selectivity but also greatly improved its bioavailability. Remarkably, in mice, B-12 did not show obvious side effects including hypertriglyceridemia as other RXRα agonists or induce hepatorenal toxicity. Together, our study describes an approach for the rational design of Ber-derived RXRα activators as novel effective antineoplastic agents for colon cancer.

NHC-Catalyzed Synthesis of Benzazole-Phosphine Ligands under an Air Atmosphere

An efficient strategy for the synthesis of benzazole-phosphine ligand precursors via N -heterocyclic carbene catalyzed aerobic oxidative cyclization reaction has been performed. The reaction displays broad functional group tolerance and high atom economy,

Intermolecular Dehydrative Coupling and Intramolecular Cyclization of Ruthenium Vinylidene Complexes Formed from Aromatic Propynes Containing Carbonyl Functionalities

A remarkable intermolecular dehydrative coupling reaction with the formation of a C?C bond was found for the vinylidene complex 2 a, yielding the dinuclear bisvinylidene complex 4 a. Complex 2 a containing 1-hydroxyindan moiety was first formed from the reaction of o-propynyl benzaldehyde 1 a with [Ru]–Cl ([Ru]=Cp(PPh3)2Ru) by a cyclization process. For analogous aldehyde 1 b containing an additional 1,3-dioxolane group on the aryl ring, similar intermolecular coupling yields the dinuclear bisvinylidene complex 4 b. However, the fluoro group on the aryl ring in aldehyde 1 c inhibits the coupling reaction, giving only the vinylidene complex 2 c. For the reactions of [Ru]–Cl in MeOH with compounds 1 f, 1 g and 1 h, each with a ketone functionality, cyclization gives vinylidene complexes 2 f, 2 g and 2 h, respectively. However, no similar intermolecular coupling was observed, instead, the intramolecular dehydration yields 8 f, 8 g and 8 h, respectively. In CDCl3, catalytic cyclization is observed for the o-propynylphenyl ketone 1 h with [Ru]–Cl at 50 °C giving the isochromene products 14 h. Furthermore, treatment of the o-propynylaryl α,β-unsaturated ketones 1 k–m and 1 n with [Ru]–Cl in MeOH affords the corresponding vinylidene complexes 10 k–m and 11 n each with 1-benzosuberone moiety in the presence of NH4PF6. These intramolecular cyclization products were formed by the addition of Cβ onto the terminal carbon of the alkene moiety. All these reaction products were characterized by spectroscopic methods. In addition, structures of complexes 4 a, and 10 l were confirmed by single crystal X-ray diffraction analysis.

An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

A simple method for the preparation of arylnaphthalene lactone natural products was developed and used to synthesize diphyllin (10), justicidin A (12), cilinaphthalide B (13), taiwanin E (15), chinensinaphthol (16), taiwanin E methyl ether (17), chinensin

Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis

A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 μM and 16.40 μM, respectively. The intracellular amastigotes assays showed IC50 = 22.00 μM (22) and 17.00 μM (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase.