PFK-158

Base Information

• Chemical Name: PFK-158
• CAS No.: 1462249-75-7
• Molecular Formula: C18H11F3N2O
• Molecular Weight: 328.29
• Mol file: 1462249-75-7.mol

Synonyms:PFK-158;PFK-158, ACT-PFK-158;(2E)-1-(4-Pyridinyl)-3-[7-(trifluoromethyl)-2-quinolinyl]-2-propen-1-one

Chemical Property of PFK-158

Chemical Property:

• Boiling Point: 466.3±45.0 °C(Predicted)
• PKA: 2.46±0.10(Predicted)
• PSA: 42.85000
• Density: 1.346±0.06 g/cm3(Predicted)
• LogP: 4.54470

Purity/Quality:

97% ^*data from raw suppliers

PFK158 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: PFK158 is an inhibitor of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 (PFKFB3; IC50 = 137 nM for human recombinant PFKFB3). It inhibits PFKFB3 and glycolysis in Jurkat cells (IC50s = 1.6 and 0.847 μM, respectively). PFK158 inhibits the growth of leukemia cells in vitro (IC50 = 0.33 μM for Jurkat cells) and reduces tumor volume in CT-26 murine colon carcinoma syngeneic model and a BxPC-3 pancreatic cancer mouse xenograft model. PFK158 also enhances activity of the anti-CTLA-4 antibody in the B16/F10 mouse model of melanoma.

Technology Process of PFK-158

There total 4 articles about PFK-158 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: 63.3%

7-(trifluoromethyl)quinoline-2-carbaldehyde (904369-15-9) + 1-pyridin-4-yl-2-(triphenyl-λ5-phiosphanylidene)ethanone (316124-45-5) → PFK158 (1462249-75-7)

Guidance literature:

In toluene; for 17h; Reflux;

Reference yield: 33.0%

methyl (4-pyridyl) ketone (1122-54-9) + 7-(trifluoromethyl)quinoline-2-carbaldehyde (904369-15-9) → PFK158 (1462249-75-7)

Guidance literature:

With triethylamine; In isopropyl alcohol; at 20 ℃; for 20h; Reflux;

Reference yield:

methyl (4-pyridyl) ketone (1122-54-9) → PFK158 (1462249-75-7)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine / tetrachloromethane / 1 h / Reflux

2: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere; Reflux

3: sodium hydroxide / methanol; water / 20 °C

4: toluene / 17 h / Reflux

With bromine; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; tetrachloromethane; water; toluene;

upstream raw materials:

methyl (4-pyridyl) ketone

7-(trifluoromethyl)quinoline-2-carbaldehyde

1-pyridin-4-yl-2-(triphenyl-λ⁵-phiosphanylidene)ethanone

4-bromoacetylpyridine hydrobromide