Ganetespib

Base Information

• Chemical Name: Ganetespib
• CAS No.: 888216-25-9
• Molecular Formula: C₂₀H₂₀N₄O₃
• Molecular Weight: 364.404
• Hs Code.: 2933990090
• Mol file: 888216-25-9.mol

Synonyms:3-(2,4-Dihydroxy-5-isopropylphenyl)-4-(1-methylindol-5-yl)-5-hydroxy-4H-1,2,4-triazole; 5-[2,4-Dihydroxy-5-(1-methylethyl)phenyl]-2,4-dihydro-4-(1-methyl-1H-indol-5-yl)-3H-1,2,4-triazol-3-one;

Chemical Property of Ganetespib

Chemical Property:

• PKA: 7.38±0.20(Predicted)
• PSA: 96.33000
• Density: 1.39
• LogP: 3.66620
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml)

Purity/Quality:

99%, ^*data from raw suppliers

3-[2,4-Dihydroxy-5-(propan-2-yl)phenyl]-4-(1-methyl-1H-indol-5-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Ganetespib (888216-25-9) is an inhibitor of heat shock protein 90 (IC50 = 19 nM, canine C2 malignant mast cells; 4 nM, canine BR malignant mast cells) binding to the N-terminal ATP site.1? It displayed potent cytotoxicity against a panel of 57 transformed cell lines of both hematologic and solid tumors? with IC50’s between 14 and 280 nM.2 Ganetespib enhanced T-cell-mediated killing of human melanoma cells and potentiated responses to anti-CTLA4 and anti-PD1 therapy via upregulation of interferon response genes.3 In multiple clinical trials for various cancers.

Technology Process of Ganetespib

There total 10 articles about Ganetespib 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: 99.0%

C34H32N4O3 (958888-26-1) → 5-[2,4-dihydroxy-5-(1-methylethyl)phenyl]-2,4-dihydro-4-(1-methyl-1H-indol-5-yl)-3H-1,2,4-triazole-3-one (888216-25-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 3h;

Reference yield:

5-nitroindole (6146-52-7) → 5-[2,4-dihydroxy-5-(1-methylethyl)phenyl]-2,4-dihydro-4-(1-methyl-1H-indol-5-yl)-3H-1,2,4-triazole-3-one (888216-25-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

1.2: 20 °C

2.1: palladium on activated charcoal; hydrogen / ethanol / 5 h / 50 °C

3.1: triethylamine / dichloromethane / 0.17 h / 0 °C

3.2: 0.25 h

4.1: hydrazine hydrate / 1,4-dioxane / 102 °C

5.1: acetic acid / ethanol / 1 h / 80 °C

6.1: potassium hexacyanoferrate(III); sodium hydroxide / ethanol / 8 h / 100 °C

7.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 20 °C

With palladium on activated charcoal; hydrogen; sodium hydride; hydrazine hydrate; acetic acid; triethylamine; sodium hydroxide; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

1-methyl-5-nitro-1H-indole (29906-67-0) → 5-[2,4-dihydroxy-5-(1-methylethyl)phenyl]-2,4-dihydro-4-(1-methyl-1H-indol-5-yl)-3H-1,2,4-triazole-3-one (888216-25-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: palladium on activated charcoal; hydrogen / ethanol / 5 h / 50 °C

2.1: triethylamine / dichloromethane / 0.17 h / 0 °C

2.2: 0.25 h

3.1: hydrazine hydrate / 1,4-dioxane / 102 °C

4.1: acetic acid / ethanol / 1 h / 80 °C

5.1: potassium hexacyanoferrate(III); sodium hydroxide / ethanol / 8 h / 100 °C

6.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 20 °C

With palladium on activated charcoal; hydrogen; hydrazine hydrate; acetic acid; triethylamine; sodium hydroxide; potassium hexacyanoferrate(III); In 1,4-dioxane; methanol; ethanol; dichloromethane;

upstream raw materials:

C₃₄H₃₂N₄O₃

5-nitroindole

1-methyl-5-nitro-1H-indole

1-methyl-1H-indol-5-amine

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