7570-47-0

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-5-NITROINDOLE is used as a reactant for the preparation of various pharmaceutical compounds, including:
1. βCyanoindoles: These compounds are utilized as building blocks in the synthesis of various biologically active molecules.
2. Methanoindoles: These are important intermediates in the development of drugs targeting specific receptors or enzymes.
3. Protein kinase C theta (PKCθ) inhibitors: PKCθ is a critical enzyme involved in various cellular processes, and its inhibition can have therapeutic benefits in treating certain diseases.
4. Tubulin polymerization inhibitors: These compounds can disrupt the normal functioning of tubulin, a protein essential for cell division, and are being explored for their potential in cancer therapy.
5. Peptide-mimetic protease-activated receptor-1 (PAR-1) antagonists: These molecules can block the activity of PAR-1, a receptor involved in various physiological processes, and may have applications in treating conditions like thrombosis and inflammation.
6. Cytosolic phospholipase A2α: This enzyme plays a role in the production of inflammatory mediators, and its inhibition can be beneficial in treating inflammatory diseases.
7. Cyclooxygenase (COX) inhibitors: These compounds can inhibit the activity of COX enzymes, which are involved in the production of prostaglandins, and are commonly used as anti-inflammatory and analgesic agents.
8. Serotonin 5-HT6 Receptor Ligands: These molecules can modulate the activity of the serotonin 5-HT6 receptor, which is implicated in various neurological and psychiatric disorders.
Used in Chemical Industry:
2-METHYL-5-NITROINDOLE is used as a building block for the synthesis of heterocyclic β-substituted alanine derivatives, which are important components in the development of novel pharmaceuticals and other chemical compounds with potential applications in various industries.

InChI:InChI=1/C9H8N2O2/c1-6-4-7-5-8(11(12)13)2-3-9(7)10-6/h2-5,10H,1H3

Upstream product

• 115210-54-3 2-methyl-5-nitroindoline 
• 95-20-5 2-methyl-1H-indole 
• 53512-36-0 2-Methyl-3-methylthio-5-nitroindol 
• 100-16-3 4-nitrophenylhydrazone 
• 67-64-1 acetone 
• 100-01-6 4-nitro-aniline 
• 1363421-86-6 2-methyl-5-azido-1H-indole 
• 75-05-8 acetonitrile 

Downstream Products

• 7570-49-2 5-amino-2-methylindole 
• 147646-73-9 3-benzyl-2-methyl-5-nitro-indole 
• 120627-43-2 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole 
• 3558-17-6 2-Methyl-5-nitro-1H-indole-3-carboxaldehyde 
• 51226-47-2 1,2-dimethyl-5-nitro-1H-indole 
• 115210-54-3 2-methyl-5-nitroindoline 
• 852042-41-2 1-(3,5-dimethyl-phenyl)-2-methyl-5-nitro-1H-indole 
• 872675-11-1 1-(diphenylmethyl)-2-methyl-5-nitro-1H-indole 
• 872675-13-3 2-[1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]ethanol 
• 872675-12-2 ethyl [1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]oxoacetate 
• 872675-16-6 methyl 4-[2-[5-amino-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]ethoxy]benzoate 
• 872675-14-4 methyl 4-[2-[1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]ethoxy]benzoate 
• 164083-71-0 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole-3-glyoxylic acid amide 
• 1025821-83-3 (1-Benzyl-2-methyl-5-nitro-1H-indol-3-yl)-oxo-acetyl chloride 

Relevant academic research and scientific papers

Trichloroisocyanuric acid (TCCA) and carboxamide interactions in TCCA/NaNO2 triggered nitration of pyrrole and indole in aqueous aprotic media: A kinetic correlation of solvent properties with reactivity

This study deals with the trichloroisocyanuric acid (TCCA) interactions with carboxamides like formamide (FMA), N,N′-dimethyl formamide (DMF), and N,N′-dimethyl acetamide (DMA) interactions during the nitration of heterocyclic compounds (HC) like pyrrole and indole in the presence of excess of [NaNO2] over the concentrations of all other reactants. All the reactions were performed in aqueous acetonitrile media containing carboxamide under acid-free conditions. Kinetics of the reactions revealed first order in [nitrating agent] and [HC] under otherwise similar conditions. To gain an insight into the reactive species and role of added carboxamide (FAA, DMF, DMA, etc.), the observed rates of the nitration reaction (log k) were analyzed as a function of (1/D), ([D ? 1]/[2D + 1]), mole fraction (nx), and volume (%) of carboxamide, 1/viscosity, density refractive index function), and Hildebrand solubility parameter plots. Linear regression analysis gave very good correlation coefficients (R2 values), which indicate the importance of several solvent properties in addition to the role of dielectric constant (D) of the reaction media. Multiple linear solvent energy relationships suggested by Abraham, Koppel, Palm, and Taft also afforded very good correlation coefficient (R2 values), showing the importance of cumulative effect of solvent properties. Besides these features, the negative entropies of activation (?S#) suggest greater solvation in the transition state. Isokinetic temperature (β) values for different protocols were very close to the experimental temperature range (303-323 K), indicating the importance of both enthalpy and entropy factors in controlling the reaction.

SMALL MOLECULE DIRECT INHIBITORS OF KEAP1-NRF2 PROTEIN-PROTEIN INTERACTION

This patent document diclsoes novel compounds and methods of preventing or treating diseases or conditions related to Keapl-Nrf2 interaction activity by use of the novel compounds. As direct inhibitors of Keapl-Nrf2 interaction, the compounds disclosed herein are more specific and free of various undesirable effects than existing indirect inhibitors, and are potential dmg candidates of chemopreventive and therapeutic agents for treatment of various diseases or conditions involving oxidative stress and/or inflammation, including but not limited to cancers, diabetes, Alzheimer's, Parkinson's, and inflammatory bowel disease including ulcerative colitis.

On the mechanism for the photooxidation of aromatic azides containing a secondary N–H bond: A sequence of intramolecular transformations with the formation of heterocyclic oximes

During the photooxidation of aromatic azides containing a secondary N–H bond at the para-position, a sequence of intramolecular transformations of nitroso oxides led to the formation of heterocyclic oximes along with the corresponding nitroso and nitro co

Indole Based Weapons to Fight Antibiotic Resistance: A Structure-Activity Relationship Study

Antibiotic resistance represents a worldwide concern, especially regarding the outbreak of methicillin-resistant Staphylococcus aureus, a common cause for serious skin and soft tissues infections. A major contributor to Staphylococcus aureus antibiotic resistance is the NorA efflux pump, which is able to extrude selected antibacterial drugs and biocides from the membrane, lowering their effective concentrations. Thus, the inhibition of NorA represents a promising and challenging strategy that would allow recycling of substrate antimicrobial agents. Among NorA inhibitors, the indole scaffold proved particularly effective and suitable for further optimization. In this study, some unexplored modifications on the indole scaffold are proposed. In particular, for the first time, substitutions at the C5 and N1 positions have been designed to give 48 compounds, which were synthesized and tested against norA-overexpressing S. aureus. Among them, 4 compounds have NorA IC50 values lower than 5.0 μM proving to be good efflux pump inhibitor (EPI) candidates. In addition, preliminary data on their ADME (absorption, distribution, metabolism, and excretion) profile is reported.

PROTEASOME ACTIVITY ENHANCING COMPOUNDS

The present invention is directed to compounds having the Formula (I), (II), (III), (IV), and (V), compositions thereof, the methods of synthesis of the compouds of interest, and to methods for the treatment of a condition associated with a dysfunction in proteostasis, such as cancer, inflammatory conditions, neurodegeneration, metabolic conditions, comprising administering an effective amount of a compound of the invention.

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death

Methuosis is a novel caspase-independent form of cell death in which massive accumulation of vacuoles derived from macropinosomes ultimately causes cells to detach from the substratum and rupture. We recently described a chalcone-like compound, 3-(2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1- one (i.e., MIPP), which can induce methuosis in glioblastoma and other types of cancer cells. Herein, we describe the synthesis and structure-activity relationships of a directed library of related compounds, providing insights into the contributions of the two aryl ring systems and highlighting a potent derivative, 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (i.e., MOMIPP) that can induce methuosis at low micromolar concentrations. We have also generated biologically active azide derivatives that may be useful for future studies aimed at identifying the protein targets of MOMIPP by photoaffinity labeling techniques. The potential significance of these studies is underscored by the finding that MOMIPP effectively reduces the growth and viability of Temozolomide-resistant glioblastoma and doxorubicin-resistant breast cancer cells. Thus, it may serve as a prototype for drugs that could be used to trigger death by methuosis in cancers that are resistant to conventional forms of cell death (e.g., apoptosis).

Synthesis and pharmacological evaluation of peptide-mimetic protease-activated receptor-1 antagonists containing novel heterocyclic scaffolds

Protease-activated receptor-1 (PAR-1) is a G-coupled receptor activated by α-thrombin and other proteases. In this paper we describe the synthesis and the pharmacological evaluation of novel peptide-mimetic antagonists (compounds 1-16) characterized by th

A Practical Approach of Continuous Processing to High Energetic Nitration Reactions in Microreactors

Continuous processing in microreactors represents a novel way for the safe and expedient conduct of high energetic reactions and potentially hazardous chemistry. Apart from handling benefits (such as minimised problems in the scale-up process), reactions in microreactors proceed under precisely controlled conditions providing improved yields and product quality compared to the batch procedure. In this paper, the potential of this technology is exemplarily determined in the crucial nitration of the pharmaceutically relevant intermediate 1-methyl-3-propyl-1H-pyrazole-5-carboxylic acid (1). Further fundamental nitration examples demonstrate the unproblematic handling of hazardous H2SO4/ HNO3 mixtures for the nitration of 2-methylindole (4) and pyridine- N-oxide (6) or even the explosive acetyl nitrate Ac2O/HNO3 (nitration of toluene, 8) in the continuous reaction mode.

Bicyclic oxazolidinones as antibacterial agents

The present invention provides compounds of formula I useful as antimicrobial agents wherein W, X, Y, R1, R2 and n are as defined in thereof.