6127-49-7

Usage

Uses

Used in Pharmaceutical Research:
2-(4-BROMO-PHENYL)-1H-INDOLE is used as a research compound for its potential therapeutic applications, including its antiviral, anticancer, and anti-inflammatory properties. It is studied for its ability to modulate different biological pathways, which could lead to the development of new drugs and treatments for various diseases.
Used in Chemical Research:
In the field of chemical research, 2-(4-BROMO-PHENYL)-1H-INDOLE serves as a chemical building block for the synthesis of various heterocyclic compounds. Its unique structure and properties make it a valuable component in the creation of new chemical entities with potential applications in various industries.
Used in Drug Development:
2-(4-BROMO-PHENYL)-1H-INDOLE is utilized in drug development as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its potential as a modulator of biological pathways and its diverse biological activities make it a promising candidate for the development of new drugs with novel mechanisms of action.

InChI:InChI=1/C14H10BrN/c15-12-7-5-10(6-8-12)14-9-11-3-1-2-4-13(11)16-14/h1-9,16H

Upstream product

• 62-53-3 aniline 
• 99-73-0 para-bromophenacyl bromide 
• 99-90-1 para-bromoacetophenone 
• 100-63-0 phenylhydrazine 
• 5705-15-7 N-benzyl-N-phenylhydrazine hydrochloride 
• 120-72-9 indole 
• 1038997-85-1 (4-bromophenyl)(2,4,6-triisopropylphenyl)iodonium triflate 
• 78133-84-3 (2-aminobenzyl)triphenylphosphonium bromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 157869-13-1 2-((4-bromophenyl)ethynyl)aniline 
• 1224876-14-5 C₂₁H₁₅BrIN 
• 589-87-7 1,4-bromoiodobenzene 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 61843-42-3 1-methyl-2-(4-bromophenyl)-1H-indole 
• 1211973-73-7 C₃₅H₂₃Br₂FN₂ 
• 1211973-76-0 C₃₆H₂₆Br₂N₂O 
• 1351939-90-6 2-amino-4-(2-(4-bromophenyl)-1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1351939-89-3 2-amino-4-(2-(4-bromophenyl)-1H-indol-3-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 83800-88-8 2-(4-bromophenyl)-3H-quinazolin-4-one 
• 1456698-55-7 2-((2-(4-bromophenyl)-1H-indol-3-yl)(4-chlorophenyl)methyl)-1H-indene-1,3(2H)-dione 
• 18600-53-8 2-(4-bromophenyl)-4H-benzo[d][1,3]oxazine-4-one 
• 1401073-72-0 2-(2-(4-bromophenyl)-1H-indol-3-yl)-1-p-tolyl-2-(m-tolylamino)ethanone 
• 1364953-11-6 N-(3-bromo-5,5-difluoroindolo[2,1-a]isoquinolin-6(5H)-ylidene)-4-methoxyaniline 
• 1364952-39-5 N-(2-bromo-1-(2-(4-bromophenyl)-1H-indol-1-yl)-2,2-difluoroethylidene)-4-methoxyaniline 

Relevant academic research and scientific papers

One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones

A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.

Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis

Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives

We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.

Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones

A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.

4-benzo five-membered ring-phenyl ketoxime ester compound as well as preparation method and application thereof

The invention discloses a 4-benzo five-membered ring- phenyl ketoxime ester compound as well as a preparation method and application thereof. The invention relates to a 4-benzo five-membered ring-phenyl oxime ester derivative shown as a formula (I), a photocuring composition and a preparation method of the 4-benzo five-membered ring-phenyl ketoxime ester derivative shown as the formula (I). The 4-benzo five-membered ring-phenyl ketoxime ester derivative molecule represented by the formula (I) has the advantages of red shift of absorption wavelength, good photoinitiation efficiency, simple synthesis steps, and wide application prospect in the field of UV-Vis-LED excitable photocureable coating or ink industrialization.

Aniline-initiated and Br?nsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR

A highly novel method of direct synthesis of 2-aryl-3-sulfenylindoles in moderate to good yields was developed via one-pot tandem reaction of readily available α-aminocarbonyl compounds and catalytic amount of benzenamines with RSSR.

Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C–H Activation Reaction

Abstract: A regioselective C2 arylation of indoles, benzothiophene and benzofuran without directing group has been accomplished using economically cheap Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst is efficiently employed to access C2 arylated heterocycles in good to excellent yield. The reusability of the catalyst is studied up to five cycles and a gram-scale synthesis has been achieved. The reaction mechanism is well supported by control experiments and literature precedents. Grapic Abstract: [Figure not available: see fulltext.]