69902-42-7

Upstream product

• 288264-28-8 N-[N-(4-bromophenyl)-N-(2,5-dimethylphenyl)amino]phthalimide 
• 10075-50-0 5-bromo-1H-indole 
• 110-13-4 2,5-hexanedione 
• 957783-22-1 tert-butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxylate 
• 1186127-11-6 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(triisopropylsilyl)-1,3-oxazole 
• 2935-44-6 hexane-2,5-diol 
• 2050-44-4 N-(2,5-dimethylphenyl)acetamide 
• 106-37-6 1.4-dibromobenzene 
• 3002-24-2 hexane-2,4-dione 
• 387819-85-4 N-(4-bromophenyl)-N-(2,5-dimethylphenyl)amine 

Downstream Products

• 18073-34-2 9-bromoellipticine 
• 18073-21-7 6-bromo-1,4-dimethyl-9-H-carbazole-3-carbaldehyde 
• 111249-52-6 3-amino-1,4-dimethyl-9H-carbazole 

Relevant academic research and scientific papers

9-Ethyl-1,4-dimethyl-6-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole and 6-bromo-9-ethyl-1,4-dimethyl-9H-carbazole

The title carbazolyl boronic ester, C22H28BNO2, (I), is a building block for the synthesis of new carbazole derivatives of potential utility as pharmaceutically active compounds. The crystal structure of (I) and of the title bromo-carbazole com-pound, C16H16BrN, (II), the synthetic precursor of (I), were solved and analysed with the aim of understanding the lack of reactivity of (I) under Suzuki cross-coupling reaction conditions. In both structures, the methyl groups are coplanar with the carbazole ring system, and the ethyl group lies out of the carbazole plane. The dioxaborolane ring of boronic ester (I) adopts a half-chair conformation but lies approximately in a planar orientation with respect of the carbazole ring system, whereas the Br atom of (II) is coplanar with the carbazole plane. In (I), the carbazole-boronic ester C - B bond length is 1.5435 (14) A, which is somewhat shorter than the usual value of 1.57 A.

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

New trimethoxybenzamides and trimethoxyphenylureas derived from dimethylcarbazole as cytotoxic agents. Part i

A convenient synthesis of novel functionalized 1,4-dimethylcarbazole derivatives containing 3,4,5-trimethoxybenzamido-ureido or N-(3,4,5- trimethoxyphenyl)ureido group starting from their corresponding indole derivatives is reported. Three derivatives pre

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.

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.

Microwave-assisted solid-acid-catalyzed friedel-crafts alkylation and electrophilic annulation of indoles using alcohols as alkylating agents

Alcohols are considered environmentally benign alkylating agents since the only by-product generated in their reactions is water. Herein, we report a microwave-assisted Friedel-Crafts alkylation and electrophilic annulation of indoles using alcohols as al

Synthesis of 2-TIPS-oxazol-5-ylboronic acid pinacol ester: efficient route to 5-(het)aryloxazoles via Suzuki cross-coupling reaction

A facile synthetic route to the new 2-TIPS-oxazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-(het)aryloxazoles. A wide range of functions on the aryl moiety ar

Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction

N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.

Solvent-free solid acid-catalyzed electrophilic annelations: A new green approach for the synthesis of substituted five-membered N-heterocycles

An effective microwave-induced, solid acid-catalyzed, environmentally benign synthesis of substituted pyrroles, indoles and carbazoles under solvent-free conditions is described. The new synthetic methodology is based on the use of a considerably strong solid acid, K-10 montmorillonite. Both the cyclialkylation of amines and annelation of pyrroles and indoles have been completed within minutes and provided excellent (75-98%) yields with practically 100% selectivity.

Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine

Novel linear thiazolocarbazoles, which are structurally very close to the natural alkaloid ellipticine, have been rapidly synthesised via imino-1,2,3-dithiazoles, themselves readily obtained by treatment of the appropriate 3-aminocarbazoles with 4,5-dichloro-1,2,3-dithiazolium chloride 1 (Appel salt).