1H-Indazol-3-amine

Base Information

• Chemical Name: 1H-Indazol-3-amine
• CAS No.: 874-05-5
• Molecular Formula: C7H7N3
• Molecular Weight: 133.153
• Hs Code.: 29339900
• European Community (EC) Number: 692-411-2
• NSC Number: 44677,348887
• DSSTox Substance ID: DTXSID5061243
• Nikkaji Number: J79.993I
• Wikidata: Q27182567
• ChEMBL ID: CHEMBL1331627
• Mol file: 874-05-5.mol

Synonyms:1H-indazol-3-amine;1H-indazole-3-amine

Chemical Property of 1H-Indazol-3-amine

Chemical Property:

• Vapor Pressure: 7.16E-06mmHg at 25°C
• Melting Point: 156-157 °C
• Refractive Index: 1.78
• Boiling Point: 376.6 °C at 760 mmHg
• PKA: 14.89±0.40(Predicted)
• Flash Point: 209.5 °C
• PSA: 54.70000
• Density: 1.367 g/cm³
• LogP: 1.72630
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 133.063997236
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

97% ^*data from raw suppliers

1H-Indazol-3-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 34-25-36/37/38-22
• Safety Statements: 26-36/37/39-45-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NN2)N
• General Description: 1H-Indazol-3-ylamine (3-aminoindazole) is a key structural component in the development of P1/P1′ substituted cyclic urea HIV protease inhibitors, as demonstrated in the synthesis and evaluation of compounds like DMP 850 and DMP 851. Its incorporation into these inhibitors aims to enhance intracellular antiviral potency by improving cell penetration and binding affinity to HIV protease. The modifications of P1/P1′ residues in these analogues contribute to their enzyme inhibitory activity, whole-cell antiviral efficacy, and pharmacokinetic properties, highlighting its role as a pharmacophore in potential HIV therapeutics.

Technology Process of 1H-Indazol-3-amine

There total 1 articles about 1H-Indazol-3-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 3-aminoindazole (874-05-5) + o-toluidine (95-53-4)

Guidance literature:

With ammonium sulfide;

Reference yield: 94.0%

3-aminoindazole (874-05-5) + 4-amino-o-xylene (95-64-7) → N-(3,4-dimethylphenyl)-1,2,3-benzotriazin-4(3H)-imine

Guidance literature:

With tert.-butylhydroperoxide; iodine; tetra-(n-butyl)ammonium iodide; In propan-1-ol; at 80 ℃; for 12h;

DOI:10.1039/c9gc03567b

Reference yield: 94.0%

n-butyl isonitrile (2769-64-4) + 2-(2-bromoethyl)benzaldehyde (22901-09-3) + 3-aminoindazole (874-05-5) → N-butyl-5,6-dihydroindazolo[3',2':2,3]imidazo[5,1-a]isoquinolin-14-amine

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 78 ℃; for 1h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior;

DOI:10.1016/j.tetlet.2020.152101

Downstream raw materials:

2H-indazole

1,2,3-benzotriazin-4(3H)-one

(1H-Indazol-3-yl)-(3-pyrrolidin-1-yl-propyl)-amine

1-(3-Pyrrolidin-1-yl-propyl)-1H-indazol-3-ylamine

Refernces

Synthesis, antiviral activity and pharmacokinetics of P1/P1′ substituted 3-aminoindazole cyclic urea HIV protease inhibitors

10.1016/S0960-894X(02)01064-8

The study focuses on the synthesis, antiviral activity, and pharmacokinetics of P1/P10 substituted 3-aminoindazole cyclic urea HIV protease inhibitors. The aim was to enhance the intracellular antiviral potency of nonsymmetrical 3-aminoindazoles, DMP 850 and DMP 851, by modifying the P1/P10 residues to improve cell penetration. The chemicals used included various substituted benzyllithiums, dihydrazone 1, Raney nickel, and 1,10-carbonyldiimidazole for synthesis; 3-cyano4-fluoro-benzylbromide and hydrazine hydrate for introducing the 3-aminoindazole group; and benzyl bromide or butyl iodide for alkylation to form mono-alkylated cyclic ureas. These chemicals served to create a series of P1/P10 substituted cyclic urea analogues, which were then tested for their enzyme binding affinity, whole cell antiviral activity, plasma protein binding, resistance profile, and pharmacokinetics to assess their potential as therapeutics for inhibiting the human immunodeficiency virus protease (HIV-Pr).