PFI-1

Base Information

• Chemical Name: PFI-1
• CAS No.: 1403764-72-6
• Molecular Formula: C₁₆H₁₇N₃O₄S
• Molecular Weight: 347.395
• Mol file: 1403764-72-6.mol

Synonyms:4e96;QCR-192;PFI-1;CS-1362;

Chemical Property of PFI-1

Chemical Property:

• PSA: 96.12000
• LogP: 3.70300
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10mg/mL

Purity/Quality:

98% min ^*data from raw suppliers

PFI-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: PFI 1 is a BET bromodomain inhibitor that exhibits inhibitory activity at BRD2 and BRD4. PFI-1 is a selective BET bromodomain inhibitor with activity at BRD2 (IC50 = 98 nM) and BRD4 (IC50 = 220 nM). PFI 1 induces apoptosis and G1 cell cycle arrest in BET inhibitor-sensitive cell lines (MV4;11). PFI 1 also downregulates Aurora B expression in MV4;11 cells.
• Uses: PFI-1 is used as a selective protein interaction inhibitor targetting BET bromodomains, used as regulators required for efficient expression of several growth promoting and anti-apoptotic genes.

Technology Process of PFI-1

There total 3 articles about PFI-1 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: 34.0%

o-Methoxybenzenesulfonyl chloride (10130-87-7) + 6-amino-3-methyl-3,4-dihydroquinazolin-2(1H)-one → 2-methoxy-N-(3-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)benzenesulfonamide (1403764-72-6)

Guidance literature:

With pyridine; In dichloromethane; for 2h;

DOI:10.1021/jm3010515

Reference yield:

3-methyl-3,4-dihydro-2(1H)-quinazolinone (24365-65-9) → 2-methoxy-N-(3-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)benzenesulfonamide (1403764-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid; potassium nitrate / 0 °C

2: hydrogen / acetic acid / 16 h / 20 °C / 760.05 Torr

3: pyridine / dichloromethane / 2 h

With pyridine; sulfuric acid; hydrogen; potassium nitrate; In dichloromethane; acetic acid;

DOI:10.1021/jm3010515

Reference yield:

3-methyl-6-nitro-3,4-dihydroquinazolin-2(1H)-one (1253226-04-8) → 2-methoxy-N-(3-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)benzenesulfonamide (1403764-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; acetic acid / 16 h / 1551.49 Torr

2: pyridine / dichloromethane / 1 h / 20 °C / Cooling with ice

With pyridine; hydrogen; acetic acid; In dichloromethane;

upstream raw materials:

3-methyl-3,4-dihydro-2(1H)-quinazolinone

o-Methoxybenzenesulfonyl chloride

3-methyl-6-nitro-3,4-dihydroquinazolin-2(1H)-one

Refernces

• 1、 Fish, Paul V.,Filippakopoulos, Panagis,Bish, Gerwyn,Brennan, Paul E.,Bunnage, Mark E.,Cook, Andrew S.,Federov, Oleg,Gerstenberger, Brian S.,Jones, Hannah,Knapp, Stefan,Marsden, Brian,Nocka, Karl,Owen, Dafydd R.,Philpott, Martin,Picaud, Sarah,Primiano, Michael J.,Ralph, Michael J.,Sciammetta, Nunzio,Trzupek, John D.. "Identification of a chemical probe for bromo and extra C-terminal bromodomain inhibition through optimization of a fragment-derived hit". . p. 9831 - 9837. Retrieved 2013/01/16.