2439-68-1

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
5-(Benzyloxy)-1-methyl-1H-indole is used as a chemical intermediate for the synthesis of various organic compounds, particularly in the pharmaceutical and medicinal chemistry industries. Its unique structure allows it to serve as a precursor for the development of new drugs and therapeutic agents.
Used in Research and Development:
In the field of organic chemistry, 5-(Benzyloxy)-1-methyl-1H-indole is utilized as a research compound to explore its potential biological activities and to understand its interactions with biological systems. This knowledge can contribute to the advancement of drug discovery and the creation of novel therapeutic agents.
Used in Drug Synthesis:
5-(Benzyloxy)-1-methyl-1H-indole is employed as a key component in the synthesis of pharmaceuticals, where its structural features can be leveraged to create new molecules with specific therapeutic properties. Its versatility in chemical reactions makes it a valuable building block for medicinal chemists.
Used in Biochemical Studies:
5-(Benzyloxy)-1-methyl-1H-indole is also used in biochemical studies to investigate its interactions with enzymes, receptors, and other biological targets. Understanding these interactions can provide insights into the development of drugs that modulate these targets for the treatment of various diseases.
Used in Drug Design:
5-(Benzyloxy)-1-methyl-1H-indole is utilized in the design of new drugs, where its structural elements can be incorporated into drug candidates to enhance their efficacy, selectivity, and pharmacokinetic properties. Its unique features make it a promising candidate for the development of innovative therapeutic agents.

InChI:InChI=1/C16H15NO/c1-17-10-9-14-11-15(7-8-16(14)17)18-12-13-5-3-2-4-6-13/h2-11H,12H2,1H3

Upstream product

• 1215-59-4 5-benzyloxy-1H-indole 
• 74-88-4 methyl iodide 

Downstream Products

• 16382-45-9 1-methyl-5-benzyloxy-α-oxo-3-indoleacetyl chloride 
• 596105-58-7 4-(5-benzyloxy-1-methyl-1H-indol-3-yl)-butan-2-one 
• 125313-90-8 3-(5-benzyloxy-1-methyl-3-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione 
• 13523-92-7 1-methyl-1H-indol-5-ol 
• 58630-07-2 5-(benzyloxy)-1-methyl-1H-indole-3-carbaldehyde 
• 2521-11-1 2-(5-benzyloxy-1-methyl-indol-3-yl)-ethylamine 
• 1292285-86-9 C₂₁H₂₄N₂O₃ 
• 1292285-84-7 C₁₈H₁₆N₂O₃ 
• 1292285-85-8 C₁₈H₁₈N₂O₃ 
• 161460-13-5 (5-(benzyloxy)-1-methyl-1H-indol-3-yl)(phenyl)methanone 
• 1334225-01-2 butyl 5-(benzyloxy)-1-methyl-1H-indole-3-carboxylate 
• 1198229-52-5 C₃₃H₃₁NO₂ 
• 1158209-20-1 5-benzyloxy-1-methyl-1H-indole-3-sulfonyl chloride 
• 72254-94-5 1-methyl-2,3-dihydro-indol-5-ol 

Relevant academic research and scientific papers

Discovery of a Class of Potent and Selective Non-competitive Sentrin-Specific Protease 1 Inhibitors

Sentrin-specific proteases (SENPs) are responsible for the maturation of small ubiquitin-like modifiers (SUMOs) and the deconjugation of SUMOs from their substrate proteins. Studies on prostate cancer revealed an overexpression of SENP1, which promotes prostate cancer progression as well as metastasis. Therefore, SENP1 has been identified as a novel drug target against prostate cancer. Herein, we report the discovery and biological evaluation of potent and selective SENP1 inhibitors. A structure-activity relationship (SAR) of the newly identified pyridone scaffold revealed allosteric inhibitors with very attractive in vitro ADMET properties regarding plasma binding and plasma stability for this challenging target. This study also emphasizes the importance of biochemical mode of inhibition studies for de novo designed inhibitors.

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide

Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).

Method for preparing indole compound through air oxidation catalyzed by N-hydroxyphthalimide

The invention discloses a method for preparing an indole compound through non-transition metal catalyzed air oxidation. According to the method, the low-cost N-hydroxyphthalimide is used as a catalystand air is used as an oxidizing agent, wherein indoline compounds are oxidized in an organic solvent, and synthesis of the indoline compounds is achieved. The method has the advantages of simple reaction operation, low reaction cost, high yield, mild conditions, no heavy metal pollution and the like.

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.

HISTONE DEMETHYLASE INHIBITORS

The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrido[3,4-d]pyrimidin-4-one derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition of histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

Palladium-catalyzed regioselective aerobic oxidative C-H/N-H carbonylation of heteroarenes under base-free conditions

Clearing the air! By using a balloon pressure of CO, the direct oxidative carbonylation of various heteroarenes with different alcohols was achieved in good to high yields with air as the oxidant in the presence of PdCl 2(PPh3)2 (see scheme). Notably, this transformation was carried out under base-free conditions. The reaction showed remarkably high regioselectivity and presents an environmentally benign protocol for the synthesis of carboxylic acid derivatives.

SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN

Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and pro-drugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain)

Indolyne experimental and computational studies: Synthetic applications and origins of selectivities of nucleophilic additions

Efficient syntheses of 4,5-, 5,6-, and 6,7-indolyne precursors beginning from commercially available hydroxyindole derivatives are reported. The synthetic routes are versatile and allow access to indolyne precursors that remain unsubstituted on the pyrrole ring. Indolynes can be generated under mild fluoride-mediated conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with varying degrees of regioselectivity; distortion energies control regioselectivity and provide a simple model to predict the regioselectivity in the nucleophilic additions to indolynes and other unsymmetrical arynes. This model has led to the design of a substituted 4,5-indolyne that exhibits enhanced nucleophilic regioselectivity.

Indolynes as electrophilic indole surrogates: Fundamental reactivity and synthetic applications

A mild method to access a variety of substituted indole derivatives has been developed. The strategy relies on the generation of highly reactive indolyne intermediates, which function as electrophilic indole surrogates.

Structure-based design leads to the identification of lithium mimetics that block mania-like effects in rodents. Possible new GSK-3β therapies for bipolar disorders

More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3β (GSK-3β) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3β inhibitors. The best ligand in this series (having a Ki value of 4.6 nM against GSK-3β) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3β inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.