81881-74-5

Usage

Uses

Used in Pharmaceutical Synthesis:
C-(1H-INDOL-5-YL)-METHYLAMINE is used as a reactant for the preparation of various pharmaceutical agents, including HIV-1 integrase inhibitors, inhibitors of Gli1-mediated transcription in the Hedgehog pathway, SCIO-469-like compounds for the inhibition of p38 MAP kinase, and 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles as protein kinase C theta (PKC θ) inhibitors.
Used in the Synthesis of Vigabatrin Bioisosteres:
C-(1H-INDOL-5-YL)-METHYLAMINE is used in the synthesis of Vigabatrin (V253000) bioisosteres, which are inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT). These compounds have potential applications in the treatment of neurological disorders, such as epilepsy, by modulating the GABAergic system.
Used in the Development of Non-covalent Thrombin Inhibitors:
C-(1H-INDOL-5-YL)-METHYLAMINE is also used as a reactant for the preparation of non-covalent thrombin inhibitors. These inhibitors have potential applications in the prevention and treatment of thrombotic disorders, such as deep vein thrombosis and pulmonary embolism, by targeting the thrombin enzyme and modulating its activity.

InChI:InChI=1/C9H10N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H,6,10H2

Upstream product

• 15861-24-2 1H-indole-5-carbonitrile 
• 10075-50-0 5-bromo-1H-indole 
• 1075-25-8 indole-5-methanol 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 1670-87-7 SD-169 

Downstream Products

• 401907-15-1 1-(1H-indol-5-ylmethyl)-3-phenethylurea 
• 401907-14-0 1-(1H-indol-5-ylmethyl)-3-phenethylthiourea 
• 259537-85-4 2,2,2-Trifluoro-N-(2-methoxyethyl)-N-[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl] acetamide 
• 259538-85-7 2-[3-({[(2 R)-1-(Cyclohexyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2 H)-pyrazinyl]-N-(1 H-indol-5-ylmethyl)acetamide 
• 1146213-75-3 tert-butyl 5-((4-(4-fluorobenzyl)piperazine-1-carboxamido)methyl)-1H-indole-1-carboxylate 
• 267875-62-7 tert-butyl ((1H-indol-5-yl)methyl)carbamate 
• 15861-24-2 1H-indole-5-carbonitrile 
• 1196-69-6 1H-indole-5-carboxaldehyde 

Relevant academic research and scientific papers

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation

Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.

Effects of ruthenium hydride species on primary amine synthesis by direct amination of alcohols over a heterogeneous Ru catalyst

Heterogeneously catalysed synthesis of primary amines by direct amination of alcohols with ammonia has long been an elusive goal. In contrast to reported Ru-based catalytic systems, we report that Ru-MgO/TiO2 acts as an effective heterogeneous catalyst for the direct amination of a variety of alcohols to primary amines at low temperatures of ca. 100 °C without the introduction of H2 gas. The present system could be applied to a variety of alcohols and provides an efficient synthetic route for 2,5-bis(aminomethyl)furan (BAMF), an attention-getting biomonomer. The high catalytic performance can be rationalized by the reactivity tuning of Ru-H species using MgO. Spectroscopic measurements suggest that MgO enhances the reactivity of hydride species by electron donation from MgO to Ru.

Generation of novel family of reductases from PCR based library for the synthesis of chiral alcohols and amines

Biocatalysis has shown tremendous potential in the synthesis of drugs and drug intermediates in the last decade. Screening of novel biocatalysts from the natural genome space is the growing trend to replenish the harsh chemical synthetic routes, commonly used in the pharmaceutical and chemical industry. Here, we report a novel ketoreductase (KERD) and a nitrile reductase isolated from the PCR based library generated from the genome of Rhodococcus ruber and Bacillus subtilis, respectively. Both the proteins are hypothetical in nature as there is no putative homology found in the database, although both the enzymes have significant activity towards the synthesis of chiral alcohols and amines. Enzyme activity over a wide range of substrates (aromatic and aliphatic) for both the novel catalysts was observed. From the unique gene sequence to activity over a broad range of substrate and >99% conversion at higher concentrations (100 mM and above) entitles both the hypothetical enzymes as novel. The novel KERD has shown >99% selectivity for the synthesis of (S)-phenylethanol which makes it a potential candidate for industrial catalysis. The novel nitrile reductase has also shown promising activity for the synthesis of (R)-2-phenylethanolamine, which is a difficult moiety to synthesize chemically. In this report, starting from a homology based library, two highly potent whole cell biocatalysts are obtained.

Selective Hydrogenation of Nitriles to Primary Amines by using a Cobalt Phosphine Catalyst

A general procedure for the catalytic hydrogenation of nitriles to primary amines by using a non-noble metal-based system is presented. Co(acac)3 in combination with tris[2-(dicyclohexylphosphino)ethyl]phosphine efficiently catalyzes the selective hydrogenation of a wide range of (hetero)aromatic and aliphatic nitriles to give the corresponding amines.

NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions

A series of seven novel NImNHP-type pincer imidazolylphosphine ruthenium complexes has been synthesized and fully characterized. The use of hydrogenation of benzonitrile as a benchmark test identified [RuHCl(CO)(NImNHPtBu)] as the most active catalyst. With its stable Ru-BH4 analogue, in which chloride is replaced by BH4, a broad range of (hetero)aromatic and aliphatic nitriles, including industrially interesting adiponitrile, has been hydrogenated under mild and base-free conditions.

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

Screening of NOS activity and selectivity of newly synthesized acetamidines using RP-HPLC

Nitric Oxide Synthase (NOS) inhibitors could play a powerful role in inflammatory and neurodegenerative diseases. In this work, novel acetamidine derivatives of NOS were synthesized and the inhibitor activity was evalued. To screen the activity and selectivity, the l-citrulline residue, after the enzymatic NOS assay, was derivatized with o-phthaldialdehyde/N-acetyl cysteine (OPA/NAC) and then evaluated by RP-HPLC method with fluorescence detection.All compounds did not affect the activity of endothelial and neuronal isoforms, while nine of them possessed a percentage of iNOS activity at 10 μM lower than 50%, and were selected for IC50 evaluation. Among them, a compound emerged as a very potent (IC50 of 53 nM) and selective iNOS inhibitor.

THERAPEUTIC INHIBITORY COMPOUNDS

The invention provides compounds of Formula I and Formula II: A-B-C-D-E-F-G-J (I) C-D-E-F-G-J (II) wherein A, B, C, D, E, F, G, and J have any of the values defined in the specification, and salts thereof. The compounds are useful for inhibiting plasma kallikrein, and for treating a disease or condition in an animal where inhibition of plasma kallikrein is indicated.

NEW INHIBITORS OF CYCLOPHILINS AND USES THEREOF

The present invention relates to a compound of formula (I): Formula (I), wherein: - n is 0, 1 or 2; - A is in particular CH or N; - X is in particular CO, SO2, CS, and R1 is in particular H, - R2 is a group of formula NR3R4 or OR5, R3 and R4 being in particular H, and R5 an alkyl group, - R6 is in particular H or an alkyl group, and - R7 is in particular an aryl group, for its use in the prevention and/or the treatment of viral pathologies or infections.