structure of 3-Iodo-6-methyl-1H-indazol-5-amine

3-Iodo-6-methyl-1H-indazol-5-amine

CAS No.: 1000343-40-7
M. Wt: 273.074
M. Fa: C8H8IN3
InChI Key: KHCABMPYPIFRLE-UHFFFAOYSA-N

Names and Identifiers of 3-Iodo-6-methyl-1H-indazol-5-amine

CAS Number

1000343-40-7

IUPAC Name

3-iodo-6-methyl-2H-indazol-5-amine

InChI

InChI=1S/C8H8IN3/c1-4-2-7-5(3-6(4)10)8(9)12-11-7/h2-3H,10H2,1H3,(H,11,12)

InChIKey

KHCABMPYPIFRLE-UHFFFAOYSA-N

Canonical SMILES

CC1=CC2=NNC(=C2C=C1N)I

Physical and chemical properties of 3-Iodo-6-methyl-1H-indazol-5-amine

Acidity coefficient

13.03±0.40(Predicted)

Boiling Point

449.3±40.0 °C at 760 mmHg

Density

2.0±0.1 g/cm3

Exact Mass

272.976288

Flash Point

225.5±27.3 °C

Index of Refraction

1.811

LogP

2.44

Molecular Formula

C8H8IN3

Molecular Weight

273.074

PSA

54.70000

Storage condition

2-8°C

Vapour Pressure

0.0±1.1 mmHg at 25°C

Applications of 3-Iodo-6-methyl-1H-indazol-5-amine

3-Iodo-6-methyl-1H-indazol-5-amine has potential applications in various fields:

  • Pharmaceutical Development: Due to its IDO1 inhibitory activity, it is being investigated for its potential use in cancer therapies and other diseases where modulation of the kynurenine pathway is beneficial.
  • Organic Synthesis: The compound serves as an intermediate in synthesizing more complex organic molecules, making it valuable in heterocyclic chemistry.

Interaction Studies of 3-Iodo-6-methyl-1H-indazol-5-amine

Interaction studies involving 3-Iodo-6-methyl-1H-indazol-5-amine focus on its binding affinity with various biological targets. Techniques such as surface plasmon resonance or isothermal titration calorimetry are commonly employed to assess how well this compound interacts with proteins or enzymes involved in disease processes. Preliminary results suggest promising interactions that warrant further investigation to elucidate mechanisms of action and optimize therapeutic potential.

Biological Activity of 3-Iodo-6-methyl-1H-indazol-5-amine

3-Iodo-6-methyl-1H-indazol-5-amine exhibits significant biological activity, primarily through its role as an inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1). This inhibition affects the kynurenine pathway, which is critical for tryptophan metabolism. The compound has demonstrated anti-proliferative activity in certain cancer cell lines by inducing apoptosis via the activation of the p53/MDM2 pathway. Additionally, it interacts with various enzymes and proteins, influencing cellular processes such as signaling pathways and gene expression.