Epacadostat (INCB024360)

Base Information

• Chemical Name: Epacadostat (INCB024360)
• CAS No.: 1204669-58-8
• Molecular Formula: C₁₁H₁₃BrFN₇O₄S
• Molecular Weight: 438.237
• Mol file: 1204669-58-8.mol

Synonyms:(Z)-N-(3-bromo-4-fluorophenyl)-N'-hydroxy-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole-3-carboxamidine;Epacadostat(INCN024360);Epacadostat(INCB024360);[C(Z)]-4-[[2-[(Aminosulfonyl)amino]ethyl]amino]-N-(3-bromo-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide;Epacadostat;1,2,5-Oxadiazole-3-carboximidamide, 4-[[2-[(aminosulfonyl)amino]ethyl]amino]-N-(3-bromo-4-fluorophenyl)-N'-hydroxy-, [C(Z)]-

Chemical Property of Epacadostat (INCB024360)

Chemical Property:

• Boiling Point: 700.9±70.0 °C(Predicted)
• PKA: 7.65±0.69(Predicted)
• PSA: 176.14000
• Density: 2.01±0.1 g/cm3(Predicted)
• LogP: 2.74210
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

Epacadostat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Epacadostat is an inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1) with an IC50 value of 7.1 nM in HeLa cells that demonstrates little activity against the related enzymes IDO2 or tryptophan 2,3-dioxygenase (TDO). It has been shown to promote T and natural killer-cell growth, to increase IFN-γ production, and to reduce conversion to regulatory T (Treg)-like cells in a coculture system of human allogeneic lymphocytes with either dendritic cells or tumor cells. Epacadostat can also inhibit tumor growth in tumor-bearing mice in a lymphocyte-dependent manner.
• Uses: Epacadostat is a potent and novel indoleamine 2,3-dioxygenase (IDO1) inhibitor with IC50 of 10 nM. It has high selectivity over IDO2 and tryptophan 2,3-dioxygenase (TDO).

Technology Process of Epacadostat (INCB024360)

There total 32 articles about Epacadostat (INCB024360) 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: 95.4%

N-[2-({4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)ethyl]sulfamide (1204669-70-4) → 4-({2-[(aminosulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboximidamide (1204669-37-3,1204669-58-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 2 - 20 ℃; for 16h; Solvent;

Reference yield: 81.7%

N-[2-({4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)ethyl]sulfamide (1204669-70-4) → (Z)-4-({2-[(aminosulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide (1204669-37-3,1204669-58-8)

Guidance literature:

With trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; water; at 0 - 16 ℃; for 5h; Temperature; Time; Large scale;

Reference yield: 81.0%

(9H-fluoren-9-yl)methyl N-(2-((4-(4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl)amino)ethyl)sulfamoylcarbamate (1771804-78-4) → 4-({2-[(aminosulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboximidamide (1204669-37-3,1204669-58-8)

Guidance literature:

With 2,2',2''-triaminotriethylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 3.08333h;

upstream raw materials:

(Ν-(2-((4-(4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl)amino)ethyl)tert-butylsulfamoyl)carbamate

4-(3-bromo-4-fluorophenyl)-3-{4-[(2-methoxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one

4-(3-bromo-4-fluorophenyl)-3-{4-[(2-hydroxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one

2-({4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)ethyl methanesulfonate

Refernces

• 1、 Stanley, Christopher P.,Maghzal, Ghassan J.,Ayer, Anita,Talib, Jihan,Giltrap, Andrew M.,Shengule, Sudhir,Wolhuter, Kathryn,Wang, Yutang,Chadha, Preet,Suarna, Cacang,Prysyazhna, Oleksandra,Scotcher, Jenna,Dunn, Louise L.,Prado, Fernanda M.,Nguyen, Nghi,Odiba, Jephthah O.,Baell, Jonathan B.,Stasch, Johannes-Peter,Yamamoto, Yorihiro,Di Mascio, Paolo,Eaton, Philip,Payne, Richard J.,Stocker, Roland. "Singlet molecular oxygen regulates vascular tone and blood pressure in inflammation". . p. 548 - 552. Retrieved 2019/03/06.
• 2、 Yue, Eddy W.,Sparks, Richard,Polam, Padmaja,Modi, Dilip,Douty, Brent,Wayland, Brian,Glass, Brian,Takvorian, Amy,Glenn, Joseph,Zhu, Wenyu,Bower, Michael,Liu, Xiangdong,Leffet, Lynn,Wang, Qian,Bowman, Kevin J.,Hansbury, Michael J.,Wei, Min,Li, Yanlong,Wynn, Richard,Burn, Timothy C.,Koblish, Holly K.,Fridman, Jordan S.,Emm, Tom,Scherle, Peggy A.,Metcalf, Brian,Combs, Andrew P.. "INCB24360 (Epacadostat), a Highly Potent and Selective Indoleamine-2,3-dioxygenase 1 (IDO1) Inhibitor for Immuno-oncology". . p. 486 - 491. Retrieved 2017/05/19.