145692-57-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-INDOLE-3-CARBONITRILE, 6-METHOXYis used as a building block for the synthesis of various pharmaceuticals due to its versatile chemical structure and biological activities, including its anti-cancer, anti-inflammatory, and anti-microbial properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1H-INDOLE-3-CARBONITRILE, 6-METHOXYis utilized as a precursor in the development of new agrochemicals, leveraging its chemical properties to create compounds with potential applications in pest control and crop protection.
Used in Dye Intermediates Industry:
1H-INDOLE-3-CARBONITRILE, 6-METHOXYis employed as a key intermediate in the production of dyes, taking advantage of its chemical structure to synthesize a range of dye compounds used in various industries.
Used in Research and Development:
1H-INDOLE-3-CARBONITRILE, 6-METHOXYis used as a precursor in the research and development of novel therapeutic agents, exploring its potential in creating new medicines with improved efficacy and reduced side effects.

InChI:InChI=1/C10H8N2O/c1-13-8-2-3-9-7(5-11)6-12-10(9)4-8/h2-4,6,12H,1H3

Upstream product

• 1261024-50-3 6-methoxy-1H-indole-3-carbaldehyde oxime 
• 3189-13-7 6-methoxylindole 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 70555-46-3 6-methoxy-1H-indole-3-carbaldehyde 

Downstream Products

• 1248576-70-6 (S)-6-(3-cyano-1-cyclobutyl-6-(difluoromethoxy)-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide 
• 1248585-37-6 C₂₆H₃₈F₂N₂OSn 
• 876739-47-8 C₁₉H₁₈FN₃O 
• 1443382-52-2 C₁₉H₁₇N₃O₂ 
• 1443382-51-1 C₁₉H₁₈N₂O₂S 
• 1443382-53-3 C₂₅H₂₁N₃O₂ 
• 876733-61-8 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile 

Relevant academic research and scientific papers

Metabolism of the phytoalexins camalexins, their bioisosteres and analogues in the plant pathogenic fungus Alternaria brassicicola

The metabolism of the phytoalexins camalexin (1), 1-methylcamalexin (10) and 6-methoxycamalexin (11) by Alternaria brassicicola and their antifungal activity is reported. This work establishes that camalexins are slowly biotransformed (ca. six days) to the corresponding indole-3-thiocarboxamides, which are further transformed to the indole-3-carboxylic acids. These metabolites are substantially less inhibitory to A. brassicicola than the parent camalexins, indicating that these enzyme-mediated transformations are detoxifications. In addition, analyses of the metabolism of synthetic isomers and bioisosteres of camalexin (1) indicate that isomers of camalexin in the thiazole ring are not metabolized. Based on these results, the potential intermediates that lead to formation of indole-3-thiocarboxamides are proposed.

Structure-activity relationship (SAR) optimization of 6-(Indol-2-yl) pyridine-3-sulfonamides: Identification of potent, selective, and orally bioavailable small molecules targeting hepatitis C (HCV) NS4B

A novel, potent, and orally bioavailable inhibitor of hepatitis C RNA replication targeting NS4B, compound 4t (PTC725), has been identified through chemical optimization of the 6-(indol-2-yl)pyridine-3-sulfonamide 2 to improve DMPK and safety properties.

Discovery of N-(4′-(indol-2-yl)phenyl)sulfonamides as novel inhibitors of HCV replication

A series of novel 2-phenylindole analogs were synthesized and evaluated for activity in subgenomic HCV replicon inhibition assays. Several compounds containing small alkyl sulfonamides on the phenyl ring exhibiting submicromolar EC50 values against the genotype 1b replicon were identified. Among these, compound 25d potently inhibited the 1b replicon (EC50 = 0.17 μM) with 147-fold selectivity with respect to cytotoxicity. Compound 25d was stable in the presence of human liver microsomes and had a good pharmacokinetic profile in rats with an IV half-life of 4.3 h and oral bioavailability (F) of 58%.

Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4- thiadiazoles

A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity.

NITROGENATED HETEROCYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to novel compounds having a xanthine oxidase inhibitory effect and an uricosuric effect and pharmaceutical compositions comprising the same as an active ingredient. That is, the present invention relates nitrogen-containing heterocyclic compounds represented by the following general formula (I): wherein Y1 represents N or C(R4) ; Y2 represents N or C(R5) ; R4 and R5 independently represent an alkyl group, a hydrogen atom etc. ; one of R1 and R2 represents an optionally substituted aryl group, an alkoxygroup or an optionally substituted heterocyclic group; the other of R1 and R2 represents a haloalkyl group, a cyanogroup, ahalogenatometc.; and R3 represents a 5-tetrazolyl group or a carboxy group, and pharmaceutically acceptable salts thereof, and pharmaceutical compositions comprising the same as an active ingredient.

METHODS FOR TREATING HEPATITIS C

In accordance with the present invention, compounds that inhibit viral replication, preferably Hepatitis C Virus (HCV) replication, have been identified, and methods for their use provided. In one aspect of the invention, compounds useful in the treatment

Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: Analogues of cytotoxic marine bis(indole) alkaloid

2,4-Bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis(3'-indolyl)pyrazine were synthesized and evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. These compounds demonstrated significant inhibitory effects in the growth of a range of cancer cell lines. 2,4-Bis(3'-indolyl)thiazole displayed selective cytotoxicity against certain leukemia cell lines with GI50 values in the low micromolar range while the substituted derivatives showed a broad spectrum of cytotoxic activity. 3,5-Bis(3'-indolyl)-2(1H)pyrazinone and 3,6- bis[3'-(N-methyl-indolyl)]pyrazine possessed strong inhibitory activity against a wide range of human tumor cell lines. The mechanism of action remained unknown. The results suggested that 2,4-bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis[3'-(N-methyl-indolyl)] pyrazine offer potential as lead compounds for the discovery of anticancer agents. (C) 2000 Elsevier Science Ltd.