14501-66-7

Basic information

• Product Name: 1,4-DIMETHYL-3-FORMYLCARBAZOLE
• Synonyms: 1,4-DIMETHYL-3-FORMYLCARBAZOLE
• CAS NO: 14501-66-7
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.27
• Product Categories: Heterocycles
• Mol File: 14501-66-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 445.7°Cat760mmHg
• Flash Point: 228.1°C
• Appearance: /
• Density: 1.238g/cm³
• Vapor Pressure: 3.87E-08mmHg at 25°C
• Refractive Index: 1.741
• CAS DataBase Reference: 1,4-DIMETHYL-3-FORMYLCARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIMETHYL-3-FORMYLCARBAZOLE(14501-66-7)
• EPA Substance Registry System: 1,4-DIMETHYL-3-FORMYLCARBAZOLE(14501-66-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 14501-66-7(Hazardous Substances Data)

Usage

General Description

1,4-DIMETHYL-3-FORMYLCARBAZOLE is a chemical compound with the molecular formula C14H13NO. It is a carbazole derivative with two methyl groups and a formyl group attached to the 1,4-positions of the carbazole ring. 1,4-DIMETHYL-3-FORMYLCARBAZOLE is commonly used in organic synthesis and pharmaceutical research due to its potential biological activities. It has been studied for its anti-cancer, anti-inflammatory, and anti-microbial properties. 1,4-DIMETHYL-3-FORMYLCARBAZOLE has also been explored for its potential use as a fluorescent material in organic light-emitting diodes (OLEDs) and as a dye in organic solar cells. Its unique structure and potential applications make it a valuable compound in various fields of science and industry.

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

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

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 
• 66604-68-0 2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide 
• 18073-33-1 6-methylellipticine 
• 1618136-61-0 C₂₈H₃₃N₃O₆S 
• 56501-52-1 6-methyl-9-hydroxyellipticine 
• 1618136-72-3 2-(N-Boc-2-aminoethoxy)ethyl-9-hydroxy-6-methylellipticinium chloride 
• 1618136-76-7 2-(2-aminoethoxy)ethyl-9-hydroxy-6-methylellipticinium chloride 
• 1618136-81-4 C₂₄H₂₉N₄O₃⁽¹⁺⁾*Cl^(1-) 
• 1618136-86-9 C₂₄H₂₈N₅O₄⁽¹⁺⁾*Cl^(1-) 

Relevant articles and documents

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.

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.