156571-69-6

Basic information

• Product Name: N-(Methoxymethyl)-1H-indole-2-carboxamide
• Synonyms: N-(Methoxymethyl)-1H-indole-2-carboxamide;1H-Indole-2-carboxylic acid methoxy-methyl-amide;N-Methoxy-N-Methyl-1H-Indole-2-Carboxamide
• CAS NO: 156571-69-6
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.22518
• Mol File: 156571-69-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 147-149 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• Boiling Point: 426.7±18.0 °C(Predicted)
• Appearance: /
• Density: 1.248±0.06 g/cm3(Predicted)
• PKA: 14.96±0.30(Predicted)
• CAS DataBase Reference: N-(Methoxymethyl)-1H-indole-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Methoxymethyl)-1H-indole-2-carboxamide(156571-69-6)
• EPA Substance Registry System: N-(Methoxymethyl)-1H-indole-2-carboxamide(156571-69-6)

Safety Data

• Hazardous Substances Data: 156571-69-6(Hazardous Substances Data)

Usage

Description

N-(Methoxymethyl)-1H-indole-2-carboxamide, also known as MMICA, is a chemical compound belonging to the class of indole carboxamides. It is a derivative of indole, a heterocyclic aromatic organic compound, featuring a methoxymethyl group attached to the nitrogen atom and a carboxamide group at the carbon-2 position of the indole ring. MMICA's unique structure and reactivity endow it with potential applications in pharmaceutical and medicinal chemistry, as well as in organic synthesis and material science.

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 
• 58881-45-1 Indole-2-carbonyl chloride 
• 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 
• 552-89-6 2-nitro-benzaldehyde 
• 16714-25-3 2-azidobenzaldehyde 

Downstream Products

• 1373438-10-8 (E)-N'-((1H-indol-2-yl)(phenyl)methylene)-5-bromo-2-hydroxybenzohydrazide 
• 1373438-11-9 C₂₂H₁₆BrN₃O₂ 
• 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 

Relevant articles and documents

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.]

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.