77894-69-0

Basic information

• Product Name: 1-Methyl-1H-indazol-4-ylamine
• Synonyms: 1-Methyl-1H-indazol-4-ylamine;1-Methyl-1H-indazole-4-amine;1-Methyl-1H-indazol-4-amine;1H-Indazol-4-aMine,1-Methyl-;4-AMino-1-Methylindazole;1-Methyl-4-aMino-1h-indazole;1-methylindazol-4-amine
• CAS NO: 77894-69-0
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.18
• Product Categories: pharmacetical
• Mol File: 77894-69-0.mol

Chemical Properties

• Boiling Point: 321.6 °C at 760 mmHg
• Flash Point: 148.3 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 0.000295mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1-Methyl-1H-indazol-4-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-1H-indazol-4-ylamine(77894-69-0)
• EPA Substance Registry System: 1-Methyl-1H-indazol-4-ylamine(77894-69-0)

Safety Data

• Hazardous Substances Data: 77894-69-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
1-Methyl-1H-indazol-4-ylamine is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure and basic properties make it a valuable component in the design and synthesis of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
As a building block in organic synthesis, 1-Methyl-1H-indazol-4-ylamine is used to construct more complex organic molecules. Its reactivity and structural features facilitate the creation of a wide range of chemical entities for various applications, including but not limited to, agrochemicals, dyes, and materials science.
Used in Research and Development:
In the field of research and development, 1-Methyl-1H-indazol-4-ylamine serves as a key compound for exploring the properties and potential applications of indazole derivatives. Its synthesis and modification can lead to the discovery of new chemical entities with improved pharmacological profiles or novel functionalities.
Used in Biomedical Research:
1-Methyl-1H-indazol-4-ylamine is utilized in biomedical research to investigate the role of indazole derivatives in biological systems. Its interaction with biological targets can provide insights into the development of new therapeutic agents or the understanding of disease mechanisms.

InChI:InChI=1/C8H9N3/c1-11-8-4-2-3-7(9)6(8)5-10-11/h2-5H,9H2,1H3

Upstream product

• 26120-43-4 1-methyl-4-nitro-1H-indazole 
• 603-83-8 3-nitro-o-tolylamine 
• 2942-40-7 nitro-4 indazole 
• 7440-44-0 pyrographite 
• 365427-30-1 4-bromo-1-methyl-1H-indazole 
• 64-17-5 ethanol 

Downstream Products

• 369652-67-5 2-[(1-methyl-1H-indazol-4-yl)amino]-3-nitrobenzoic acid 
• 82013-51-2 2-methyl-4-amino-2H-indazole 
• 735331-25-6 N-(4-tert-butylbenzyl)-N'-(1-methyl-1H-indazol-4-yl)urea 
• 735331-13-2 N-(2,4-dichlorobenzyl)-N'-(1-methyl-1H-indazol-4-yl)urea 
• 581810-82-4 N-(1-methyl-1H-indazol-4-yl)-N'-[4-(1-piperidinyl)benzyl]urea 
• 41748-71-4 4-aminoindazole 
• 581810-83-5 N-[3-fluoro-4-(1-piperidinyl)benzyl]-N'-(1-methyl-1H-indazol-4-yl)urea 
• 581810-84-6 N-(1-methyl-1H-indazol-4-yl)-N'-[4-(1-pyrrolidinyl)benzyl]urea 
• 581810-86-8 N-[4-(1-azepanyl)benzyl]-N'-(1-methyl-1H-indazol-4-yl)urea 
• 581810-87-9 N-[4-(1-azepanyl)-3-fluorobenzyl]-N'-(1-methyl-1H-indazol-4-yl)urea 
• 1378079-11-8 1-(5-Methanesulfonyl-2-methoxy-phenyl)-3-(1-methyl-1H-indazol-4-yl)-thiourea 
• 144528-23-4 1-methyl-1H-indazol-4-ol 
• 1613391-40-4 C₂₀H₁₉N₃O₄ 

Relevant articles and documents

Development of indazolylpyrimidine derivatives as high-affine EphB4 receptor ligands and potential PET radiotracers

Due to their essential role in the pathogenesis of cancer, members of the Eph (erythropoietin-producing hepatoma cell line-A2) receptor tyrosine kinase family represent promising candidates for molecular imaging. Thus, the development and preparation of novel radiotracers for the noninvasive imaging of the EphB4 receptor via positron emission tomography (PET) is described. First in silico investigations with the indazolylpyrimidine lead compound which is known to be highly affine to EphB4 were executed to identify favorable labeling positions for an introduction of fluorine-18 to retain the affinity. Based on this, reference compounds as well as precursors were developed and labeled with carbon-11 and fluorine-18, respectively. For this purpose, a protecting group strategy essentially had to be generated to prevent unwanted methylation and to enable the introduction of fluorine-18. Further, a convenient radiolabeling strategy using [11C]methyl iodide was established which afforded the isotopically labeled radiotracer in 30-35% RCY (d.c.) which is identical with the original inhibitor molecule. A spiro ammonium precursor was prepared for radiolabeling with fluorine-18. Unfortunately, the labeling did not lead to the desired 18F-radiotracer under the chosen conditions.

Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents

Recently, it has been reported that compounds bearing a sulfonamide moiety possess many types of biological activities, including anticancer activity. The present work reports the synthesis and antiproliferative evaluation of some N-(6(4)-indazolyl)benzenesulfonamides and 7-ethoxy-N-(6(4)-indazolyl) benzenesulfonamides. All compounds were evaluated for their in vitro antiproliferative activity against three tumor cell lines: A2780 (human ovarian carcinoma) A549 (human lung adenocarcinoma) and P388 (murine leukemia). The results indicated that sulfonamides 2c, 3c, 6d, 8, 13, 3b and 16 were endowed with a pharmacologically interesting antiproliferative activity with compounds 2c and 3c showing the lower IC50 (from 0.50 ± 0.09 to 1.83 ± 0.52 μM and from 0.58 ± 0.17 to 5.83 ± 1.83 μM, respectively). Moreover, these indazoles were able to trigger apoptosis through the upregulation of the typical apoptosis markers p53 and bax. As regard to the hypothetic targets of these compounds, a preliminary docking analysis showed that all compounds seemed to interact with β-tubulin, in particular compound 3b that showed the lower Ki. The cytofluorimetric analysis of the cell cycle phases indicates that all compounds, when administered at their IC 75, caused a block in the G2/M phase of the cell cycle with the generation of subpopulations of cells with a number of chromosome >4n. When the IC50s were applied we observed a prevalent block in the G0/G1 phase except for compounds 16 and 8 where a partial G2/M block was present with a concomitant decrease of cells in the G0/G1 and S phases of the cell cycle. Altogether these results suggest a possible, but not exclusive, interaction with microtubules.

TRPV1 ANTAGONISTS

Disclosed herein are compounds of Formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

TRPV1 ANTAGONISTS

Disclosed herein are compounds of formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

SUBSTITUTED BENZOFUSED DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS

The present invention relates to substituted benzofused derivatives, which can be used as vanilloid receptor ligands, method of treating diseases, conditions and/or disorders modulated by vanilloid receptors with them, and processes for preparing them.

Reduction of nitroindazoles: Preparation of new amino and chloroamino derivatives

The synthesis of chloroaminoindazoles by the reduction of the nitro group of indazoles using stannous chloride in alcoholic acid solution is reported. Using catalytic hydrogenation with palladium the expected reduction to amino-indazoles occur.{A figure is presented}. Indazole Nitro Reduction Chlorination Aminochloroindazole Heterocycle.

Structure-activity studies of a novel series of 5,6-fused heteroaromatic ureas as TRPV1 antagonists

Novel 5,6-fused heteroaromatic ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that 4-aminoindoles and indazoles are the preferential cores for the attachment of ureas. Bulky electron-withdrawing groups in the para-position of the aromatic ring of the urea substituents imparted the best in vitro potency at TRPV1. The most potent derivatives were assessed in in vivo inflammatory and neuropathic pain models. Compound 46, containing the indazole core and a 3,4-dichlorophenyl group appended to it via a urea linker, demonstrated in vivo analgesic activity upon oral administration. This derivative also showed selectivity versus other receptors in the CEREP screen and exhibited acceptable cardiovascular safety at levels exceeding the therapeutic dose.

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor

Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity, wherein X1, X2, X3, X4, X5, R5, R6, R7, R8a, R8b, R9, Z1, Z2 and L are as defined in the description.

HETEROAROMATIC UREAS WHICH MODULATE THE FUNCTION OF THE VANILLOID-1 RECEPTOR (VR1)

Compounds of formula (I): are useful as therapeutic compounds, particularly in the treatment of pain and other conditions ameliorated by the modulation of the function of the vanilloid-1 receptor (VR1).

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor

Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.