57102-98-4

Usage

Uses

9-Ethyl-9H-carbazole-3-carboxylic Acid is a useful reagent for the preparation of an oxime ester photoinitiator.

Upstream product

• 50668-21-8 3-iodo-9-ethylcarbazole 
• 57102-97-3 3-bromo-9-ethyl-9H-carbazole 
• 124-38-9 carbon dioxide 
• 86-28-2 N-ethylcarbazole 
• 68-12-2 N,N-dimethyl-formamide 
• 57103-00-1 9-ethyl-9H-carbazole-3-carbonitrile 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 62-53-3 aniline 
• 4058-18-8 methyl 4-(phenylamino)benzoate 
• 97931-41-4 3-methoxycarbonylcarbazole 
• 773873-63-5 N-ethylcarbazole-3-methyl formate 
• 86-74-8 9H-carbazole 
• 57103-07-8 9-ethyl-3,6-diiodocarbazole 
• 7570-45-8 N-ethyl-3-carbazolealdehyde 

Downstream Products

• 432506-50-8 9-ethyl-9H-carbazole-3-carboxylic acid phenylethylamide 
• 432505-71-0 9-Ethyl-9H-carbazole-3-carboxylic acid benzylamide 
• 302557-11-5 N-ethyl-3-(ω-aminopentylaminocarbonyl)-carbazole 

Relevant academic research and scientific papers

Tert -Butylhydroperoxide-Mediated Oxidation of Carbazole-3-carboxyaldehydes

Oxidation of carbazole-3-carboxyaldehydes promoted by a 70% aqueous solution of tert -butylhydroperoxide leads to the corresponding carbazole-3-carboxylic acids in good yields. This transition-metal-free oxidation protocol is attractive for the synthesis of pharmaceutically important carbazole analogues.

Coumarin-carbazole based functionalized pyrazolines: Synthesis, characterization, anticancer investigation and molecular docking

A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the N-1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, DEPT, and mass spectroscopic techniques. The in vitro cytotoxicity study of all the synthesized compounds was evaluated against HeLa, NCI-H520 and NRK-52E cell lines. Compounds 4a and 7b became the most active compounds and exhibited their potential to arrest the cell cycle progression and induce apoptosis in both the cell lines. In addition, molecular docking studies revealed a higher binding affinity of both the molecules with CDK2 protein. Based on the obtained results, a comprehensive analysis is warranted to establish the role of compounds 4a and 7b as promising cancer therapeutic agents.

MODIFIED CARBAZOLES AS THERAPEUTIC AGENTS

This disclosure relates to compounds that target microtubules, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating diseases. More particularly, this disclosure relates to modified carbazole compounds and pharmaceutical compositions thereof, methods of targeting microtubules with these compounds, and methods of treating diseases affected by microtubule disruption.

NOVEL CARBAZOLE EHOP-016 DERIVATIVES AS ANTI-CANCER AND ANTI-MIGRATORY AGENTS

A series of novel of EHop-016 derivatives is presented herein via designing and synthesizing compounds that mimics its more favorable “U-shaped” conformation that appears to be critical for inhibitory activity against Rac. Based on modeling studies on EHop-016, compounds with a more rigid structural conformation can mimic this “U-shaped” conformation would improve the anti-migration activity against metastatic cells. Compounds are disclosed that inhibit RhoGTPases that are useful for inhibiting hyperprofilerative and neoplastic diseases. Specifically, the compounds inhibit the GTPases Rac and Cdc42 that are overactive or overexpressed in signaling pathways in cancer and metastasis. Methods for treatment of cancer and hyperproliferative diseases are disclosed.

Copper(II)-Catalyzed Iodinations of Carbazoles: Access to Functionalized Carbazoles

A copper-catalyzed iodination of carbazoles has been developed. Barluenga's reagent IPy2BF4 is used to generate a soft electrophilic halonium species for the iodination of the carbazoles. This report represents the first concept of copper-catalyst-promoted electrophilic halogenation of carbazoles. We demonstrated numerous applications of this methodology synthesizing diverse carbazole derivatives, i.e., both electron-rich and electron-deficient systems.

Modified carbazoles destabilize microtubules and kill glioblastoma multiform cells

Small molecules that target microtubules (MTs) represent promising therapeutics to treat certain types of cancer, including glioblastoma multiform (GBM). We synthesized modified carbazoles and evaluated their antitumor activity in GBM cells in culture. Modified carbazoles with an ethyl moiety linked to the nitrogen of the carbazole and a carbonyl moiety linked to distinct biaromatic rings exhibited remarkably different killing activities in human GBM cell lines and patient-derived GBM cells, with IC50 values from 67 to >10,000 nM. Measures of the activity of modified carbazoles with tubulin and microtubules coupled to molecular docking studies show that these compounds bind to the colchicine site of tubulin in a unique low interaction space that inhibits tubulin assembly. The modified carbazoles reported here represent novel chemical tools to better understand how small molecules disrupt MT functions and kill devastating cancers such as GBM.

Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents

Based on the efficacy of EHop-016 as an inhibitor of migration and Rac1 activation, a new series of carbazole derivatives has been synthesized. Cytotoxic and anti-migratory effects of these compounds were evaluated in MCF-7 and MDA-MB-231 breast cancer cell lines. Preliminary investigations of their anticancer activity demonstrated that several compounds have moderate antiproliferative effects on cancer cell lines with GI50 values in the range of 13–50 μM. Furthermore, compounds 3b and 11b inhibit migration activity of metastatic cell line MDA-MB-231 by 32% and 34%, respectively. Compound 11b was shown to inhibit activation of the Rho GTPase Rac1 by 55% at 250 nM in both MDA-MB-231 and MDA-MB-435 cell lines. Compared with the IC50 of Rac1 inhibition by lead compound EHop-016 of 1.1 μM, compound 11b demonstrates 4X improved in vitro efficacy.

Mechanofluorochromism of NIR-emitting dyes based on difluoroboron β-carbonyl cyclic ketonate complexes

New difluoroboron β-carbonyl cyclic ketonate complexes CnB (n = 2, 16), in which carbazole was linked to difluoroboron β-diketonate directly, and DCnB (n = 2, 16), where two terminal carbazole units were bridged by vinyl groups to link to difluoroboron β-

Discovery of carbazole carboxamides as novel RORγt inverse agonists

A novel series of carbazole carboxamides was discovered as potent RORγt inverse agonists using a scaffold hybridization strategy. Structure-activity relationship exploration on the amide linker, carbazole ring and arylsulfone moiety of the hybrid amide 3a led to identification of potent RORγt inverse agonists. Compound 6c was found to have a good RORγt activity with an IC50 of 58.5 nM in FRET assay, and reasonable inhibitory activity in mouse Th17 cell differentiation assay (58.8% inhibition at 0.3 μM). The binding mode of carbazole carboxamides in RORγt ligand binding domain was discussed.

A Solid-State Fluorescent Material Based on Carbazole-Containing Difluoroboron β-Diketonate: Multiple Chromisms, the Self-Assembly Behavior, and Optical Waveguides

A carbazole-containing difluoroboron β-diketonate complex (BCZ), which shows strong fluorescence in both the solid state and in organic solutions, is reported. The crystalline materials of BCZ obtained from different solvents display different emission colors. Single-crystal analysis reveals that the enhanced overlap between adjacent molecules induces increased excited-state delocalization and is responsible for the variation of the emission colors from yellow to red. The emission colors of the materials are effectively tuned by external stimuli such as grinding, heating, and solvent vapor. The powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and 1H NMR studies on materials of BCZ reveal that the thermochromic properties of BCZ are closely related to the removal of solvent molecules from the crystalline powders upon heating. Moreover, uniform 1D microstructures of BCZ obtained by solvent exchange in solution exhibit optical waveguide property with low optical loss.