5-bromo-5'-phenyl-1,2',3,3'-tetrahydrospiro[2H-indole-3,2'-(1,3,4)-thiadiazole]-2-one

Base Information

• Chemical Name: 5-bromo-5'-phenyl-1,2',3,3'-tetrahydrospiro[2H-indole-3,2'-(1,3,4)-thiadiazole]-2-one
• CAS No.: 297180-15-5
• Molecular Formula: C₁₅H₁₀BrN₃OS
• Molecular Weight: 360.234
• Hs Code.: 2934999090
• Mol file: 297180-15-5.mol

Synonyms:

Chemical Property of 5-bromo-5'-phenyl-1,2',3,3'-tetrahydrospiro[2H-indole-3,2'-(1,3,4)-thiadiazole]-2-one

Chemical Property:

• PKA: 0.44±0.20(Predicted)
• Density: 1.76±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Soluble in DMSO (up to 20 mg/ml).

Purity/Quality:

99% ^*data from raw suppliers

Lipofermata >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Lipofermata (297180-15-5) is an inhibitor of fatty acid transport protein 2 (FATP2; IC50?= 4.84 μM).1?It does not inhibit glucose transport or the activity of long chain acyl-CoA synthetase. It prevented palmitate-mediated oxidative stress, induction of BiP and CHOP, and cell death in a dose-dependent manner in hsHepG2 and mINS-1E cells suggesting utility in preventing fatty acid-mediated cell death pathways and lipotoxic disease.2?Inhibition was specific for long and very long chain fatty acids but not medium (C6-C10) acids. Lipofermata abrogates lipid transport into melanoma cells and reduces melanoma growth and invasion.3
• Uses: Lipofermata is a fatty acid transport proteins (FATPs) inhibitor.

Technology Process of 5-bromo-5'-phenyl-1,2',3,3'-tetrahydrospiro[2H-indole-3,2'-(1,3,4)-thiadiazole]-2-one

There total 5 articles about 5-bromo-5'-phenyl-1,2',3,3'-tetrahydrospiro[2H-indole-3,2'-(1,3,4)-thiadiazole]-2-one 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: 73.0%

→ 5-bromo-5'-phenyl-3'H-spiro[dihydroindole-3,2'-[1,3,4]thiadiazol]-2-one (297180-15-5)

Guidance literature:

In ethanol; at 40 ℃; for 1h;

Reference yield: 51.2%

thiobenzoylhydrazine (20605-40-7) + 5-Bromo-1H-indole-2,3-dione (87-48-9) → 5-bromo-5'-phenyl-3'H-spiro[dihydroindole-3,2'-[1,3,4]thiadiazol]-2-one (297180-15-5)

Guidance literature:

In ethanol; at 40 ℃; for 12h;

DOI:10.1016/j.cclet.2013.06.001

Reference yield:

bromobenzene (108-86-1,52753-63-6) → 5-bromo-5'-phenyl-3'H-spiro[dihydroindole-3,2'-[1,3,4]thiadiazol]-2-one (297180-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: magnesium; iodine / tetrahydrofuran / 12 h / Reflux

1.2: 12 h / 0 - 20 °C

2.1: sodium carbonate / tetrahydrofuran; water / 24 h / 20 °C

2.2: pH 2

3.1: hydrazine hydrate; sodium hydroxide / water / 2 h / 2 - 4 °C

3.2: 1 h / pH 2

4.1: ethanol / 12 h / 40 °C

With hydrazine hydrate; iodine; sodium carbonate; magnesium; sodium hydroxide; In tetrahydrofuran; ethanol; water; 1.1: |Grignard Reaction / 1.2: |Grignard Reaction;

DOI:10.1016/j.cclet.2013.06.001

upstream raw materials:

thiobenzoylhydrazine

5-Bromo-1H-indole-2,3-dione

bromobenzene

Carboxymethyl dithiobenzoate