90764-90-2

Basic information

• Product Name: 3-METHYL-1H-INDAZOL-5-AMINE
• Synonyms: 3-METHYL-1H-INDAZOL-5-AMINE;3-METHYL-1H-INDAZOL-5-YLAMINE;5-Amino-3-methyl-1H-indazole;5-Amino-3-methylindazole;1H-Indazol-5-aMine, 3-Methyl-;3-methyl-2H-indazol-5-amine
• CAS NO: 90764-90-2
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.18
• Product Categories: Indazole
• Mol File: 90764-90-2.mol

Chemical Properties

• Melting Point: 232-233 °C
• Boiling Point: 209.7 °C at 760 mmHg
• Flash Point: 102.7 °C
• Appearance: /
• Density: 1.295 g/cm³
• Vapor Pressure: 0.2mmHg at 25°C
• Refractive Index: 1.736
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.91±0.40(Predicted)
• CAS DataBase Reference: 3-METHYL-1H-INDAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-1H-INDAZOL-5-AMINE(90764-90-2)
• EPA Substance Registry System: 3-METHYL-1H-INDAZOL-5-AMINE(90764-90-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 90764-90-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-1H-indazol-5-amine is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its unique structure allows for the creation of molecules with specific therapeutic properties, enhancing the range of treatments available for various medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Methyl-1H-indazol-5-amine is utilized as a building block for the synthesis of compounds with pesticidal or herbicidal properties. Its incorporation into these products can lead to more effective and targeted agricultural solutions, contributing to crop protection and yield enhancement.
Used in Material Science:
3-Methyl-1H-indazol-5-amine finds application in material science, where it may be used to develop new materials with specific properties. Its chemical structure can influence the physical and chemical characteristics of the materials it is part of, potentially leading to advancements in areas such as polymer science and nanotechnology.
Used in Organic Synthesis:
As a versatile organic compound, 3-Methyl-1H-indazol-5-amine is used in organic synthesis for the preparation of a wide range of organic compounds. Its reactivity and functional groups make it suitable for various synthetic routes, broadening the scope of organic chemistry and enabling the creation of complex molecules for diverse applications.

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

Upstream product

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Relevant articles and documents

A Preclinical Candidate Targeting Mycobacterium tuberculosis KasA

Published Mycobacterium tuberculosis β-ketoacyl-ACP synthase KasA inhibitors lack sufficient potency and/or pharmacokinetic properties. A structure-based approach was used to optimize existing KasA inhibitor DG167. This afforded indazole JSF-3285 with a 30-fold increase in mouse plasma exposure. Biochemical, genetic, and X-ray studies confirmed JSF-3285 targets KasA. JSF-3285 offers substantial activity in an acute mouse model of infection and in the corresponding chronic infection model, with efficacious reductions in colony-forming units at doses as low as 5 mg/kg once daily orally and improvement of the efficacy of front-line drugs isoniazid or rifampicin. JSF-3285 is a promising preclinical candidate for tuberculosis. Inoyama et al. disclose the optimization of an indazole antitubercular targeting the β-ketoacyl-ACP synthase KasA. A structure-based approach has overcome significant issues with mouse metabolic stability and pharmacokinetics. A preclinical drug candidate has been delivered with efficacy in a mouse model of chronic M. tuberculosis infection at 5 mg/kg dosing.

THERAPEUTIC INDAZOLES

The invention provides compounds of formula (I): and salts thereof wherein R1-R5 have any of the meanings described in the specification. The compounds are useful for treating bacterial infections (e.g. tuberculosis).

Design and synthesis of Rho kinase inhibitors (II)

In a previous study, we identified several structurally unrelated scaffolds of the Rho kinase inhibitor using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. 1H-Indazole is one of the candidate scaffolds on which a new series of potent Rho kinase inhibitors could be developed. In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied. During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells. The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells. Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out. The inhibitory potential was improved both in the cell-free enzyme assay and in the chemotaxis assay.

Design and synthesis of Rho kinase inhibitors (I)

Several structurally unrelated scaffolds of the Rho kinase inhibitor were designed using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. A docking simulation using the ligand-binding pocket of the Rho kinase model helped to comprehensively understand and to predict the structure-activity relationship of the inhibitors. This understanding was useful for developing new Rho kinase inhibitors of higher potency and selectivity. We identified several potent platforms for developing the Rho kinase inhibitors, namely, pyridine, 1H-indazole, isoquinoline, and phthalimide.

Rho-kinase inhibitors

Disclosed are compounds and derivatives thereof, their synthesis, and their use as Rho-kinase inhibitors. These compounds of the present invention are useful for inhibiting tumor growth, treating erectile dysfunction, and treating other indications mediated by Rho-kinase, e.g., coronary heart disease.

Structure-Based Design, Synthesis, and Antimicrobial Activity of Indazole-Derived SAH/MTA Nucleosidase Inhibitors

The structure-based design, synthesis, and biological activity of a novel indazole-containing inhibitor series for S-adenosyl homocysteine/methylthioadenosine (SAH/MTA) nucleosidase are described. Use of 5-aminoindazole as the core scaffold provided a structure-guided series of low nanomolar inhibitors with broad-spectrum antimicrobial activity. The implementation of structure-based methodologies provided a 6000-fold increase in potency over a short timeline (several months) and an economy of synthesized compounds.