14501-66-7

Usage

Uses

Used in Pharmaceutical Research:
1,4-DIMETHYL-3-FORMYLCARBAZOLE is used as a pharmaceutical candidate for its anti-cancer, anti-inflammatory, and anti-microbial properties. Its unique structure and potential therapeutic effects make it a valuable compound in the development of new drugs.
Used in Organic Synthesis:
1,4-DIMETHYL-3-FORMYLCARBAZOLE is utilized as a key intermediate in the synthesis of various organic compounds, contributing to the advancement of organic chemistry.
Used in Organic Light-Emitting Diodes (OLEDs):
1,4-DIMETHYL-3-FORMYLCARBAZOLE is explored as a fluorescent material in OLEDs, leveraging its unique optical properties to improve the performance and efficiency of these devices.
Used in Organic Solar Cells:
1,4-DIMETHYL-3-FORMYLCARBAZOLE is considered as a dye in organic solar cells, potentially enhancing their energy conversion efficiency and contributing to the development of sustainable energy solutions.

InChI:InChI=1/C15H13NO/c1-9-7-11(8-17)10(2)14-12-5-3-4-6-13(12)16-15(9)14/h3-8,16H,1-2H3

Upstream product

• 120-72-9 indole 
• 861207-74-1 9-formyl-1,4-dimethylcarbazole 
• 18028-55-2 1,4-dimethyl-9H-carbazole 
• 68-12-2 N,N-dimethyl-formamide 
• 1227626-87-0 C₁₇H₁₂F₆O₇S₂ 
• 95-78-3 2,5-Dimethylaniline 
• 93-61-8 N-methyl-N-phenylformamide 
• 1478-41-7 diethoxycarbonium fluoroborate 

Downstream Products

• 519-23-3 ellipticine 
• 65266-48-0 N-(2,2-diethoxyethyl)-N-(1,4-dimethyl-9H-carbazol-3-ylmethyl)-4-methylbenzenesulfonamide 
• 65266-47-9 N-(1,4-dimethylcarbazol-3-ylmethyl) aminoacetaldehyde diethyl acetal 
• 120105-80-8 3--1,4-dimethylcarbazole 
• 720696-80-0 4-(3-formyl-1,4-dimethylcarbazol-9-ylmethyl)benzoic acid 
• 18073-23-9 3-(2,2-diethoxyethyliminomethyl)-1,4-dimethylcarbazole 
• 1227626-89-2 N-(2,2-diethoxyethyl)-N-((1,4-dimethyl-9H-carbazol-3-yl)methyl)-2-nitrobenzenesulfonamide 
• 51131-85-2 9-hydroxyellipticine 
• 1618136-69-8 C₂₈H₃₆N₃O₃⁽¹⁺⁾*C₇H₇O₃S^(1-) 
• 1618136-67-6 C₂₇H₃₄N₃O₄⁽¹⁺⁾*C₇H₇O₃S^(1-) 
• 1618136-87-0 C₂₅H₃₀N₅O₃⁽¹⁺⁾*Cl^(1-) 
• 1618136-82-5 Cl^(1-)*C₂₅H₃₁N₄O₂⁽¹⁺⁾ 
• 1618136-77-8 2-(5-aminopentyl)-9-hydroxy-6-methylellipticinium chloride 
• 1618136-73-4 2-(N-Boc-5-aminopentyl)-9-hydroxy-6-methylellipticinium chloride 

Relevant academic research and scientific papers

Efficient microwave-assisted synthesis of ellipticine through N-(1,4-dimethyl-9h-carbazol-3-ylmethyl)-n-tosylaminoacetaldehyde diethyl acetal

The long-lasting problematic low yield in the D-ring cyclization of ellipticine (1a) was dramatically improved through N-(1,4-dimethylcarbazol-3- ylmethyl)-N-tosylaminoacetaldehyde diethyl acetal with microwave irradiation. The overall yield of 1a starting from indole was significantly increased by 25-fold. This new approach is superior to reported methods in yields and, reaction time, and it provides efficient access to a broad spectrum of ellipticine derivatives.

Simple method for preparing ellipticine or substituted ellipticine

The invention relates to a synthesis process for preparing ellipticine. Ellipticine is obtained through six steps of reaction and three steps of crystallization separation, the target product total yield is high, column chromatography separation is not needed for an intermediate product and the target product, and the method is particularly suitable for large-scale preparation.

Design, synthesis, DNA binding studies and evaluation of anticancer potential of novel substituted biscarbazole derivatives against human glioma U87 MG cell line

In this research paper, we report the design and synthesis of novel substituted biscarbazole derivatives which were characterized by 1H and 13C NMR, high resolution mass spectroscopy (HRMS). The SAR study of the compounds is reported

SMALL MOLECULES TARGETING REPEAT r(CGG) SEQUENCES

The invention provides a series of bioactive small molecules that target expanded r(CGG) repeats, termed r(CGG)exp, that causes Fragile X-associated Tremor Ataxia Syndrome (FXTAS). The compound was identified by using information on the chemotypes and RNA motifs that interact. Specifically, 9-hydroxy-5,11-dimethyl-2-(2-(piperidin-1-yl)ethyl)-6H-pyrido[4,3-b]carbazol-2-ium, binds the 5′CG/3′GGC motifs in r(CGG)exp and disrupts a toxic r(CGG)exp-protein complex. Specifically, dimeric compounds incorporating two 9-hydroxyellipticine analog structures can even more potently bind the 5′CGG/3′GGC motifs in r(CGG)exp and disrupts a toxic r(CGG)exp-protein complex. Structure-activity relationships (SAR) studies determined that the alkylated pyridyl and phenolic side chains are important chemotypes that drive molecular recognition of r(CGG) repeats, such as r(CGG)exp. Importantly, the compound is efficacious in FXTAS model cellular systems as evidenced by its ability to improve FXTAS-associated pre-mRNA splicing defects and to reduce the size and number of r(CGG)exp-protein aggregates.

Synthesis and evaluation of novel ellipticines as potential anti-cancer agents

Drugs that inhibit DNA topoisomerase I and DNA topoisomerase II have been widely used in cancer chemotherapy. We report herein the results of a focused medicinal chemistry effort around novel ellipticinium salts which target topoisomerase I and II enzymes with improved solubility. The salts were prepared by reaction of ellipticine with the required alkyl halide and evaluated for DNA intercalation, topoisomerase inhibition and growth inhibition against 12 cancer cell lines. Results from the topoisomerase I relaxation assay indicated that all novel ellipticine derivatives behaved as intercalating agents. At a concentration of 100 μM, specific topoisomerase I inhibition was not observed. Two of the derivatives under investigation were found to fully inhibit the DNA decatenation reaction at a concentration of 100 μM, indicative of topoisomerase II inhibition. N-Alkylation of ellipticine was found to enhance the observed growth inhibition across all cell lines and induce growth inhibition comparable to that of Irinotecan (CPT-11; GI50 1-18 μM) and in some cell lines better than Etoposide (VP-16; GI50 = 0.04-5.2 μM). 6-Methylellipticine was the most potent growth inhibitory compound assessed (GI50 = 0.47-0.9 μM). N-Alkylation of 6-methylellipticine was found to reduce this response with GI50 values in the range of 1.3-28 μM.

Ellipticines and 9-acridinylamines as inhibitors of d-alanine:d-alanine ligase

d-Alanine:d-alanine ligase (Ddl), an intracellular bacterial enzyme essential for cell wall biosynthesis, is an attractive target for development of novel antimicrobial drugs. This study focused on an extensive evaluation of two families of Ddl inhibitors encountered in our previous research. New members of both families were obtained through similarity search and synthesis. Ellipticines and 9-acridinylamines were both found to possess inhibitory activity against Ddl from Escherichia coli and antimicrobial activity against E. coli and Staphylococcus aureus. Ellipticines with a quaternary methylpyridinium moiety were the most potent among all studied compounds, with MIC values as low as 2 mg/L in strains with intact efflux mechanisms. Antimicrobial activity of the studied compounds was connected to membrane damage, making their development as antibacterial drug candidates unlikely unless analogues devoid of this nonspecific effect can be discovered.

Modifications to the Vilsmeier-Haack formylation of 1,4-dimethylcarbazole and its application to the synthesis of ellipticines

Figure represented. An improved method for the preparation of 3-formyl-1,4-dimethylcarbazole, a key intermediate in the synthesis of ellipticine, is presented. Conditions of the Vilsmeier-Haack reaction have been modified to facilitate the production of 3-formyl-1,4-dimethylcarbazole as a major product leading to an overall improvement in yield of ellipticine from 3% to 14%. This approach was also applied to the synthesis of 6-methylellipticine and 9-methoxyellipticine.

An expedient synthesis of ellipticine via Suzuki-Miyaura coupling

A simple and efficient total synthesis of ellipticine was developed via the Suzuki-Miyaura coupling of sterically sensitive 2-hydroxybenzeneboronic acid with a multifunctional aryl halide using Pd(OAc)2 as a catalyst and Cu(OAc)2·H2O as an additive in DMSO/H2O as a key step followed by double N-arylation and cyclization.

INTRAMOLECULAR CYCLIZATION OF ortho-(CYCLOHEX-2-ENYL)ANILINES SYNTHESIS OF ELLIPTICINE

A convenient method is proposed for the synthesis of the alkaloid ellipticine, which possesses a pronounced antitumoral activity.The interaction of 3-bromocyclohexene (1 equiv.) and 2,5-xylylidine (4 equiv., 150 deg C, 5 h) gave a mixture of hexa- and tetrahydrocarbazoles which was dehydrogenated in the presence of Pd/C to the key synthon 1,4-dimethylcarbazole.The formylation of the carbazole by the Vilsmeier-Haack reaction, interaction with 2,2-diethoxyethylamine, and reduction of the imine formed over Raney nickel led to 3-(2,2-diethoxyethylaminomethyl)-1,4-dimethylcarbazole, the boiling of the N-tosylate of which gave ellipticine in high yield.

Reactions of Electron-Rich Heterocycles with Orthocarboxylic Acid Derivatives, 10. - Formylation and Alkylation of Carbazoles with Ambident Dialkoxycarbenium Tetrafluoroborates

Carbazole and some derivatives were formylated regioselectively with diethoxycarbenium tetrafluoroborate.The thermodynamically more stable diethoxymethylcarbenium and trimethoxycarbenium ions exhibit ambident electrophilic reactivity as predominant alkylation reagent.