391-45-7

Usage

Uses

3-Fluoro-9H-carbazole was studied for its potential as a kinesin spindle protein inhibitor.

Upstream product

• 61272-76-2 4-fluoro-2-iodoaniline 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 330-83-6 N-(4-fluorophenyl)aniline 
• 2677-05-6 (2-chlorophenyl)(4-fluorophenyl)amine 
• 1140969-77-2 2-azido-5-fluoro-1,1'-biphenyl 
• 1140969-90-9 C₁₂H₈FN₃ 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 108-94-1 cyclohexanone 
• 371-41-5 4-Fluorophenol 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 98-80-6 phenylboronic acid 
• 2367-17-1 6-fluoro-1,2,3,4-tetrahydrocarbazole 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 95-51-2 o-chloroaniline 

Relevant academic research and scientific papers

Fluorine-substituted bimolecular carbazole derivative as well as preparation method and application thereof

The invention discloses a fluorine-substituted bimolecular carbazole derivative represented by a formula (I) or pharmaceutically acceptable salt thereof. R1, R2, R3, R4 and R5 are defined in the specification. The fluorine-substituted bimolecular carbazole derivative or the pharmaceutically acceptable salt thereof provided by the invention can be used for preparing a DNA methyltransferase inhibitor or a histone demethylase inhibitor, and in-vitro cancer cell anti-proliferation tests prove that the fluorine-substituted bimolecular carbazole derivative has anti-proliferation activity on cancer cells.

Fluorine-substituted monocarbazole derivative as well as preparation method and application thereof (by machine translation)

The invention belongs to the field of pharmaceutical chemistry, and relates to a fluorine-substituted monocarbazole derivative which is one or more of compounds represented by formula (I) and formula (II) or a pharmaceutically acceptable soluble salt formed by a compound represented by formula (II). The fluorine-substituted monocarbazole derivatives obtained in the application can be used for preparing DNA methyltransferase inhibitors or histone demethylase inhibitors. The fluorine-substituted monocarbazole derivative has an inhibitory effect on the proliferation of cancer cells and can be used for preparing medicaments for treating and/or preventing cancer. An in-vitro cancer cell proliferation inhibition test shows that the fluorine-substituted monocarbazole compound obtained by the invention shows anti-proliferation activity against human lung cancer cells (A549), human colon cancer cells (HCTCTCT116), human gastric cancer cells (MNK NK NK-45), human liver cancer cells (HepepepG2), RPMI PMI PMI PMI PMI PMI and Karpppp289. (by machine translation)

5,6-Bis(9-(2-decyltetradecyl)-6-fluoro-9H-carbazol-3-yl)naphtho[2,1-b:3,4-b']dithiophene as a Promising Donor Structure for D–A Conjugated Copolymers with a Narrow Bandgap

A new carbazole-containing naphthodithiophene derivative—heteroaromatic compound 5,6- bis[9-(2-decyltetradecyl)-9H-carbazol-3-yl]naphtho[2,1-b:3,4-b']dithiophene (M1)—has been synthesized. The compound will be used by us as a weak donor structural block for fabricating narrow-bandgap D–A conjugated polymers. The composition and structure of M1 have been confirmed by elemental analysis data, IR spectroscopy, and 1H and 13C NMR. The synthesized compound has a low HOMO energy (–5.4 eV), which is favorable for a high open-circuit voltage. Monomer M1 can be used as a promising weak donor moiety in D–A conjugated polymers for solar photovoltaics.

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.

Visible-light-promoted intramolecular C-H amination in aqueous solution: Synthesis of carbazoles

An effective and operationally simple protocol is reported for the synthesis of versatile carbazoles. With water as a co-solvent, visible-light rather than various metals is used to facilitate the conversion of readily available 2-azidobiphenyls under mild conditions. Various functionalized bioactive natural alkaloids, such as glycoborine, clausine C, clausine L, clausine H and clauszoline K, were synthesized efficiently with nitrogen as a sole byproduct. The reaction could be performed in water, acidic or alkaline buffer solutions, showing its potential for applications in biochemistry.

Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate

A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.

Palladium-Catalyzed Intramolecular C–H Amination in Water

Palladium(II) catalysis was found to be effective for intramolecular C–H amination in water. With 2-azidobiphenyls as substrates, the reaction efficiently provided various carbazoles with N2as the sole byproduct. The reaction showed high functional-group tolerance and could be used in the synthesis of several natural carbazole alkaloids. The catalytic process was promoted by water, and the reaction was inefficient in the organic solvents that were investigated.

Iron-Catalyzed Intramolecular C(sp2)-H Amination

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.

Rh(I)-catalyzed decarbonylation synthesis of carbazoles via C-N cleavage

A one-pot Rh(I)-catalyzed synthesis of 9-H carbazoles via C-N bond cleavage by activation of aldehyde C-H bonds is reported. This protocol offers good yields and tolerates a broad range of functional groups. Based on the extensive control experiments, we propose a plausible decarbonylation mechanism.

Carbazole-Containing Sulfonamides as Cryptochrome Modulators

The subject matter herein is directed to carbazole-containing sulfonamide derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, B, C, D, E, F, G, H, a, and b are accordingly described. Also provided are pharmaceutical compositions comprising the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, obesity, metabolic syndrome, Cushing's syndrome, and glaucoma.