156571-69-6

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
N-(Methoxymethyl)-1H-indole-2-carboxamide is used as a ligand for various receptors or enzymes in pharmaceutical and medicinal chemistry. Its ability to interact with biological systems makes it a promising candidate for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
MMICA is utilized as a building block or intermediate in organic synthesis, taking advantage of its unique chemical structure and reactivity to create novel compounds with potential applications in various fields.
Used in Material Science:
Due to its distinct chemical properties, N-(Methoxymethyl)-1H-indole-2-carboxamide may be employed in the development of new materials with specific properties, such as in the creation of advanced polymers, coatings, or other functional materials.

Upstream product

• 1477-50-5 Indole-2-carboxylic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 16714-25-3 2-azidobenzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 80783-99-9 N-methoxy-N-methylcinnamamide 
• 3770-50-1 2-carbethoxyindole 
• 94790-37-1 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 
• 58881-45-1 Indole-2-carbonyl chloride 

Downstream Products

• 1352805-33-4 1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-indole-2-carboxamide 
• 1352805-34-5 1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethanone 
• 1352805-35-6 1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethanol 
• 1352805-36-7 2-(1-azidoethyl)-1-(3-fluorophenyl)-1H-indole 
• 1352805-37-8 1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethanamine 
• 1352805-38-9 tert-butyl {1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethyl}carbamate 
• 1352805-39-0 tert-butyl {1-[3-chloro-1-(3-fluorophenyl)-1H-indol-2-yl]ethyl}carbamate 
• 1352805-40-3 1-[3-chloro-1-(3-fluorophenyl)-1H-indol-2-yl]ethanamine 
• 1448592-77-5 (3-bromoindole-2-yl)(2-methoxyphenyl)methanone 
• 1448592-61-7 (3-bromoindole-2-yl)(2-hydroxyphenyl)methanone 
• 486-84-0 harmane 
• 16765-79-0 1-phenyl-9H-pyrido[3,4-b]indole 
• 80360-23-2 1-(phenylsulfonyl)-1H-indole-2-carbaldehyde 
• 1382978-47-3 4-acetyl-2-[bis(trimethylsilyl)methyl]-9-(phenylsulfonyl)-4,9-dihydro-1H-pyrido[3,4-b]indol-3(2H)-one 

Relevant academic research and scientific papers

Synthesis and evaluation of cyclic nitrone derivatives as potential anti-cancer agents

Nitrones have been found to exhibit attractive biological values as immuno spin trapping agents. However, successful clinical cases of nitrone therapeutics are still lacking. Herein we report the synthesis and antiproliferative activity of a series of structurally diverse nitrone derivatives against a panel of 5 cancer cell lines, based on which indole- and pyrrole-fused were further evaluated by analogue preparation and in-vitro screening. Analogues with moderate to good potency were identified. This study shows the promise for further pursuit of nitrone-type small molecules in chemotherapy. [Figure not available: see fulltext.]

Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones

We report a remote functionalization strategy, which allows the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as an active chain-walking/functionalization catalyst, ultimately generating a stabilized η3-bound Ni(II) enolate as the key selectivity-controlling intermediate.

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.

Calcium-Catalyzed Formal [5 + 2] Cycloadditions of Alkylidene β-Ketoesters with Olefins: Chemodivergent Synthesis of Highly Functionalized Cyclohepta[ b]indole Derivatives

The calcium-catalyzed, formal [5 + 2] cycloaddition of indolyl alkylidene β-ketoesters with mono- A nd disubstituted aryl olefins to form cyclohepta[b]indole derivatives has been established. Unanticipated chemodivergence with phenyl vinyl sulfide/ether revealed a double [5 + 2] cycloaddition cascade providing ethano-bridged cyclohepta[b]indoles. Overall, the method's highlights include: (1) use of a green, calcium-based catalyst (2.5 mol % loading); (2) reaction times under 1 h; (3) mild reaction conditions; (4) substrate-derived chemodivergence; (5) functional group tolerance; and (6) examples of derivatization.

IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS

Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.

General Method for the Preparation of Indole-2-Weinreb Amides

Indole-2-Weinreb amides are obtained via thermolysis of α-azidocinnamic acid Weinreb amides in a Hemetsberger-Knittel-type cyclization. The required vinyl azides are not accessible by Knoevenagel condensation, but are obtained by cerium(IV)-mediated oxida

Asymmetric Nazarov Cyclizations Catalyzed by Chiral-at-Metal Complexes

The application of Lewis acidic chiral-at-metal complexes of iridium(III) and rhodium(III) as catalysts for the asymmetric polarized Nazarov cyclization of dihydropyran- and indole-functionalized α-unsaturated β-ketoesters is reported (overall 24 examples). For both substrate classes, catalyst loadings of 2 mol% were found to be sufficient for achieving high yields and high stereoselectivities. The cyclized dihydropyran products were isolated in 85–98% yield, with 89%–>99% ee, and trans/cis ratios of 15:1–50:1 (9 examples). The cyclized indole products were typically isolated in more than 70% yield and in up to 93% yield, typically with more than 90% ee and in up to 97% ee, and trans/cis ratios of 12:1–28:1 (15 examples). (Figure presented.).

Beta-carboline derivatives, gamma-carboline derivatives as well as preparation methods and use thereof

The invention relates to beta-carboline derivatives, gamma-carboline derivatives as well as preparation methods and use thereof. The general structural formulas of the beta-carboline derivatives and the gamma-carboline derivatives are respectively describ

The first calcium-catalysed Nazarov cyclisation

The first calcium-catalysed Nazarov cyclisation is described. The Ca(NTf2)(PF6) complex is found to be a very active catalyst for 4π electrocyclisations. The remarkable catalytic activity of this complex is attributed to its increased Lewis acidity compared to other Ca complexes. Spectroscopic studies have provided an insight into the chelating interactions between the substrate and the Ca catalyst.