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Usage

Uses

Used in Biochemical Research:
5-Amino-2-phenylindole is used as a research tool for the synthesis and study of various biochemical compounds due to its unique structure and reactivity.
Used in Pharmaceutical Industry:
5-Amino-2-phenylindole is used as an intermediate in the synthesis of pharmaceuticals for its potential therapeutic properties and ability to be incorporated into drug molecules.
Used in Dye Synthesis:
5-Amino-2-phenylindole is used as a precursor in the production of dyes, leveraging its aromatic and conjugated system to impart color and stability to the dyes.
Used in Pesticide Industry:
5-Amino-2-phenylindole is used as a component in the development of pesticides, taking advantage of its chemical properties to target and control pests effectively.

Upstream product

• 4993-87-7 5-nitro-2-phenyl-1H-indole 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 536-74-3 phenylacetylene 
• 165280-21-7 4-nitro-2-(2-phenylethynyl)aniline 
• 16720-35-7 N,N'-2,5-cyclohexadiene-1,4-diylidenebis 
• 500992-02-9 N-[(4'-nitro-2'-phenylethynyl)phenyl]butyramide 
• 120830-42-4 N,N'-[2-(1-benzoyl-2-oxo-2-phenyl-ethyl)-p-phenylene]-bis-benzamide 
• 108-86-1 bromobenzene 
• 1227410-09-4 2-boronic acid 1-N-BOC-5-(N',N'-bisBOC)aminoindole 
• 857555-71-6 2-[2,5-bis-(dimethylsulfamoyl-amino)-phenyl]-3-oxo-3-phenyl-propionic acid ethyl ester 

Downstream Products

• 4771-09-9 N-(2-phenyl-1H-indol-5-yl)acetamide 
• 748799-38-4 4,4,4-trifluoro-3-oxobutyric acid N-(2-phenyl-1H-5-indolyl)amide 

Relevant academic research and scientific papers

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Synthesis of 2-arylindole derivatives and evaluation as nitric oxide synthase and NFκB inhibitors

Development of small molecule drug-like inhibitors blocking both nitric oxide synthase and NFκB could offer a synergistic therapeutic approach in the prevention and treatment of inflammation and cancer. During the course of evaluating the biological potential of a commercial compound library, 2-phenylindole (1) displayed inhibitory activity against nitrite production and NFκB with IC50 values of 38.1 ± 1.8 and 25.4 ± 2.1 μM, respectively. Based on this lead, synthesis and systematic optimization have been undertaken in an effort to find novel and more potent nitric oxide synthase and NFκB inhibitors with antiinflammatory and cancer preventive potential. First, chemical derivatizations of 1 and 2-phenylindole-3-carboxaldehyde (4) were performed to generate a panel of N-alkylated indoles and 3-oxime derivatives 2-7. Second, a series of diversified 2-arylindole derivatives (10) were synthesized from an array of substituted 2-iodoanilines (8) and terminal alkynes (9) by applying a one-pot palladium catalyzed Sonogashira-type alkynylation and base-assisted cycloaddition. Subsequent biological evaluations revealed 3-carboxaldehyde oxime and cyano substituted 2-phenylindoles 5 and 7 exhibited the strongest nitrite inhibitory activities (IC50 = 4.4 ± 0.5 and 4.8 ± 0.4 μM, respectively); as well as NFκB inhibition (IC50 = 6.9 ± 0.8 and 8.5 ± 2.0 μM, respectively). In addition, the 6′-MeO-naphthalen-2′-yl indole derivative 10at displayed excellent inhibitory activity against NFκB with an IC50 value of 0.6 ± 0.2 μM.

COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Novel irreversible fluorescent probes targeting the 18 kDa translocator protein: Synthesis and biological characterization

The 18 kDa translocator protein (TSPO) is a mitochondrial protein whose basal density is altered in several diseases, with the result that the evaluation of its expression levels by means of molecular imaging techniques represents a promising diagnostic approach. Experimental procedures using a labeled ligand often cause loss of the bound probe, and consequently high affinity ligands covalently binding the receptor protein are needed to overcome this problem. We have previously described a series of N,N-dialkyl-(2- phenylindol-3-yl)glyoxylamides as potent and selective TSPO ligands. Starting from these derivatives, we designed novel TSPO irreversible ligands bearing an electrophilic isothiocyanato group (7, 8), together with an irreversible NBD-fluorescent probe (18). The TSPO affinity of the new irreversible ligands was measured on rat tissue homogenates by [3H]Ro 5-4864 radiobinding kinetic assays, all compounds showing high affinities for the target protein. Further biological characterization of the fluorescent irreversible TSPO probe 18 was carried out by using fluorescent spectroscopy in human glioma cells.

Straightforward selective preparation of nitro- or amino-indoles from 2-halonitroanilines and alkynes. First synthesis of 7-amino-5-nitroindoles

A one-pot selective synthesis of 2-substituted C5-, C6-, and C7-nitro- or amino-indoles has been developed from 2-halonitroanilines. These two types of nitrogen-substituted indoles have been selectively obtained by only varying the solvent used in the tandem Sonogashira coupling/heteroannulation reaction. Moreover, from commercially available 2-bromo-4,6-dinitroaniline an unprecedented in situ selective reduction of one of the nitro groups has allowed the synthesis of new 7-amino-5-nitro-2-substituted indoles.

Modulators of ATP-binding cassette transporters

Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production

Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which: G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; and Z is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.

Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production

Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which:G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; andZ is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.

Chemistry of aminophenols. Part 2: A general and efficient synthesis of indoles possessing a nitrogen substituent at the C4, C5, C6, and C7 positions

A general and efficient synthesis of indoles possessing a nitrogen substituent at the C4, C5, C6, and C7 positions has been developed. Starting from commercially available nitro 2-aminophenols, 5-, 6-, and 7-arenesulfamoylindoles were synthesized via a ba

7-(Substituted)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamines

Pyrrolo[3,2-f]quinazoline-1,3-diamine and the 7-(substituted) and 7,8-disubstituted derivatives thereof, possess anti-bacterial activity in vitro. The invention also provides compounds having other biological effects, such as synergism in vivo with sulfa drugs against bacterial infections, activity in vivo against malarial infections, and anti-cancer activity in vivo. In addition, the compounds show anti-folic acid activity in in vitro tests.