PFI3

Base Information

• Chemical Name: PFI3
• CAS No.: 1819363-80-8
• Molecular Formula: C₁₉H₁₉N₃O₂
• Molecular Weight: 321.379
• Mol file: 1819363-80-8.mol

Synonyms:PFI3;PFI-3;(E)-1-(2-Hydroxyphenyl)-3-((1R,4R)-5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)prop-2-en-1-one;(2E)-1-(2-Hydroxyphenyl)-3-[(1R,4R)-5-(2-pyridinyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]-2-propen-1-one

Chemical Property of PFI3

Chemical Property:

• PSA: 56.67000
• LogP: 2.44960
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (>25 mg/ml)

Purity/Quality:

98%,99%, ^*data from raw suppliers

PFI-?3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: PFI-3 (1819363-80-8) is a selective inhibitor of family VIII bromodomains PB1(5), SMARCA2, and SMARCA4.1 It showed complete selectivity over all non-family VIII bromodomains.? PFI-3 blocked adipogenesis in C3H10T1/2 mesenchymal cells at 20μM.Treatment of embryonic stem cells with PFI-3 led to deprivation of stemness and deregulated lineage specificity. Differentiation of trophoblast stem cells in the presence of PFI-3 was enhanced.2 Cell permeable.
• Uses: PFI-3 is a selective chemical inhibitor for SMARCA (2/4) and PBI (5) bromodomains which may result in the delay and prevention of breast cancer.

Technology Process of PFI3

There total 5 articles about PFI3 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: 80.0%

chromone-3-carboxylic acid (39079-62-4) + (1R,4R)-2-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane → (E)-1-(2-hydroxyphenyl)-3-((1R,4R)-5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)prop-2-en-1-one (1819363-80-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; at 20 ℃; Inert atmosphere;

Reference yield:

(1R,4R)-tert-butyl 5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate → (E)-1-(2-hydroxyphenyl)-3-((1R,4R)-5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)prop-2-en-1-one (1819363-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol; 1,4-dioxane / 0.5 h

2: N-ethyl-N,N-diisopropylamine / ethanol / 3 h / 20 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; ethanol;

DOI:10.1021/acs.jmedchem.6b00012

Reference yield:

tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (134003-84-2,174823-32-6) → (E)-1-(2-hydroxyphenyl)-3-((1R,4R)-5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)prop-2-en-1-one (1819363-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene; tetrahydrofuran / 16 h / 110 °C

2: hydrogenchloride / methanol; 1,4-dioxane / 0.5 h

3: N-ethyl-N,N-diisopropylamine / ethanol / 3 h / 20 °C

With hydrogenchloride; potassium tert-butylate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; toluene;

DOI:10.1021/acs.jmedchem.6b00012

upstream raw materials:

tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

2-bromo-pyridine

chromone-3-carboxylic acid

Refernces

• 1、 He, Yali,Miller, Duane D.,Pfeffer, Lawrence M.,Sacher, Joshua R.,Sims, Michelle M.,Wang, Yinan,Yang, Chuanhe. "Novel structural-related analogs of PFI-3 (SRAPs) that target the BRG1 catalytic subunit of the SWI/SNF complex increase the activity of temozolomide in glioblastoma cells". . . Retrieved 2021/12/08.