131666-74-5

Basic information

• Product Name: 1H-Indazole-3-acetic acid, Methyl ester
• Synonyms: 1H-Indazole-3-acetic acid, Methyl ester;Methyl 2-(1H-indazol-3-yl)acetate
• CAS NO: 131666-74-5
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.1986
• Mol File: 131666-74-5.mol

Chemical Properties

• Boiling Point: 353.3±17.0 °C(Predicted)
• Appearance: /
• Density: 1.285±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.56±0.40(Predicted)
• CAS DataBase Reference: 1H-Indazole-3-acetic acid, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indazole-3-acetic acid, Methyl ester(131666-74-5)
• EPA Substance Registry System: 1H-Indazole-3-acetic acid, Methyl ester(131666-74-5)

Safety Data

• Hazardous Substances Data: 131666-74-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
1H-Indazole-3-acetic acid, methyl ester is used as a pharmaceutical candidate for its potential anti-inflammatory and anti-tumor properties. It is being studied for its ability to modulate various biological pathways and mechanisms, offering therapeutic benefits in treating inflammatory and neoplastic conditions.
Used in Organic Synthesis and Chemical Reactions:
1H-Indazole-3-acetic acid, methyl ester serves as a valuable precursor in organic synthesis, enabling the creation of new compounds with potential applications in various industries. Its reactivity and functional groups make it a useful building block for developing novel chemical entities and advancing chemical research.
Used in Chemical Research:
As a member of the indazole class, 1H-Indazole-3-acetic acid, methyl ester contributes to the understanding of the structure-activity relationships and pharmacological profiles of related compounds. Its study aids in the discovery of new drug targets and the optimization of lead compounds for improved efficacy and safety.

Upstream product

• 26663-42-3 2-(1H-indazol-3-yl)acetic acid 
• 67-56-1 methanol 
• 101714-15-2 2-(1H-indazol-3-yl)acetonitrile 
• 174180-42-8 2-methyl-2-propanyl 3-(bromomethyl)-1H-indazole-1-carboxylate 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 140926-26-7 methyl 1-(4-bromo-2-fluorobenzyl)-1H-indazole-3-acetate 
• 124955-71-1 1-(4-bromo-2-fluorobenzyl)-1H-indazole-3-acetic acid 
• 1412449-54-7 Methyl 2-(1-(4-chlorobenzoyl)-1H-indazol-3-yl)acetate 
• 1408237-72-8 N-(4-hydroxy-3,5-dimethylphenyl)-2-(1-iso-propyl-1H-indazol-3-yl)-acetamide 

Relevant articles and documents

Discovery and Optimization of Orally Bioavailable Phthalazone and Cinnolone Carboxylic Acid Derivatives as S1P2 Antagonists against Fibrotic Diseases

Idiopathic pulmonary fibrosis (IPF) is a chronic and progressive lung disease. Current treatments only slow down disease progression, making new therapeutic strategies compelling. Increasing evidence suggests that S1P2 antagonists could be effective agents against fibrotic diseases. Our compound collection was mined for molecules possessing substructure features associated with S1P2 activity. The weakly potent indole hit 6 evolved into a potent phthalazone series, bearing a carboxylic acid, with the aid of a homology model. Suboptimal pharmacokinetics of a benzimidazole subseries were improved by modifications targeting potential interactions with transporters, based on concepts deriving from the extended clearance classification system (ECCS). Scaffold hopping, as a part of a chemical enablement strategy, permitted the rapid exploration of the position adjacent to the carboxylic acid. Compound 38, with good pharmacokinetics and in vitro potency, was efficacious at 10 mg/kg BID in three different in vivo mouse models of fibrotic diseases in a therapeutic setting.

C3-CARBON LINKED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION

This invention provides Degronimers that have carbon-linked E3 Ubiquitin Ligase targeting moieties (Degrons), which can be linked to a targeting ligand for a protein that has been selected for in vivo degradation, and methods of use and compositions thereof as well as methods for their preparation.

INDOMETHACIN ANALOGS FOR THE TREATMENT OF CASTRATE-RESISTANT PROSTATE CANCER

Provided are compositions for inhibiting a biological activity of an aldoketo reductase family 1, member C3 (AKR1 C3) polypeptide. In some embodiments, the compositions are indomethacin derivatives that are AKR1 C3-specific inhibitors. Also provided are methods for producing disclosed indomethacin derivatives that substantially lack cyclooxygenase inhibitory activity but that have AKR1C3 inhibitory activity, methods for inhibiting AKR1C3 polypeptide biological activities, and methods for treating prostate tumors in subjects.

Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

A library of approximately 40 N1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2′-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets.

Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

A library of approximately 40 N1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2′-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets.

DPPH radical scavenging activity of paracetamol analogues

Biochemical studies suggest a direct relationship between the radical scavenging activity of paracetamol (I) and its antipyretic and analgesic action. To evaluate the effect of chemical modifications on the radical scavenging activity of compounds of type I, analogues 1-14 were prepared and submitted to a stable free radical (DPPH; 1,1-diphenyl-2-picryl-hydrazyl) assay. All paracetamol derivatives showed a significant higher efficiency than the parent compound. This study showed that radical scavenging activity can be increased by decreasing the phenolic ortho substituents steric hindrance or by introducing substituents on the acyl moiety like an indazole ring or the ionic N-methyl morpholinium group. A significant activating effect was also observed by replacing the 1,4-acylamidophenol with a 1,4-acylamidonaphthol system.

Design and synthesis of pyridone inhibitors of non-nucleoside reverse transcriptase

Next generation NNRTIs are sought which possess both broad spectrum antiviral activity against key mutant strains and a high genetic barrier to the selection of new mutant viral strains. Pyridones were evaluated as an acyclic conformational constraint to

Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof

Oxophthalazinyl acetic acids having benzothiazole side chains are prepared by reacting an oxophthalazinyl thioacetamide acetate with hydrogen sulfide and a nitrophenyl compound having a reactive group such that the benzothiazole side chain may be formed by ring closure involving the thioacetamide group. The oxophthalazinyl thioacetamide may be prepared by reacting the corresponding cyanomethyloxophthalazinyl acetate with hydrogen sulfide in the presence of tertiary amines. Analogous indazole and oxopyridopyridazinone acetic acids may be prepared similarly, as well as oxophthalazinyl, indazole and oxopyridopyridazinone acetic acids having thiazolopyridinyl side chains.

1H-indazole-3-acetic acids as aldose reductase inhibitors

Certain 1-(heteroaryl or aryl)methyl-1H--indazole-3-acetic acid derivatives, and their pharma-ceutically-acceptable esters and salts, are inhibitors of the aldose reductase enzyme, and so are useful in the treatment of diabetic complications.