1204669-37-3

Basic information

• Product Name: IDO inhibitor 1
• Synonyms: IDO inhibitor 1;4-[[2-[(Aminosulfonyl)amino]ethyl]amino]-N'-(3-bromo-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;N-(3-bromo-4-fluorophenyl)-N-hydroxy-4-{[2-(sulfamoylamino)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide;IDO inhibitor 1,Epacadostat;Epacadostat (INCB024360, IDO inhibitor 1)
• CAS NO: 1204669-37-3
• Molecular Formula: C₁₁H₁₃BrFN₇O₄S
• Molecular Weight: 438.2328232
• Mol File: 1204669-37-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Solubility: insoluble in H2O; ≥19.35 mg/mL in DMSO; ≥34.75 mg/mL in EtOH with ultrasonic
• CAS DataBase Reference: IDO inhibitor 1(CAS DataBase Reference)
• NIST Chemistry Reference: IDO inhibitor 1(1204669-37-3)
• EPA Substance Registry System: IDO inhibitor 1(1204669-37-3)

Safety Data

• Hazardous Substances Data: 1204669-37-3(Hazardous Substances Data)

Usage

Biological Activity

ido inhibitor 1 is a potent and novel indoleamine-2,3 dioxygenase (ido) inhibitor with ic50 value <100 nm.ido is an enzyme that catalyzes the degradation of the essential amino acid l-tryptophan to n-formylkynurenine and permits tumor cells to escape the immune system.

Upstream product

• 656-64-4 3-bromo-4-fluoroaniline 
• 914471-43-5 3‐(4‐amino‐1,2,5‐oxadiazol‐3‐yl)‐4‐(3‐bromo‐4‐fluorophenyl)‐1,2,4‐oxadiazol‐5‐one 
• 1771804-78-4 (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 
• 1204669-70-4 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 
• 1204669-69-1 (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 
• 1204669-67-9 3‐{4‐[(2‐aminoethyl)amino]‐1,2,5‐oxadiazol‐3‐yl}‐4‐(3‐bromo‐4‐fluorophenyl)‐1,2,4‐oxadiazol‐5‐one hydrochloride 
• 1204669-68-0 tert‐butyl N‐[2‐({4‐[4‐(3‐bromo‐4‐fluorophenyl)‐5‐oxo‐1,2,4‐oxadiazol‐3‐yl]‐1,2,5‐oxadiazol‐3‐yl}amino)ethyl]carbamate 
• 1204669-66-8 3-(4-((2-azidoethyl)amino)-1,2,5-oxadiazole-3-yl)-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazole-5(4H)-one 
• 1204669-65-7 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 
• 1204669-64-6 4-(3-bromo-4-fluorophenyl)-3-{4-[(2-hydroxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one 
• 1204669-63-5 4-(3-bromo-4-fluorophenyl)-3-{4-[(2-methoxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one 
• 1204669-62-4 N-(3-bromo-4-fluorophenyl)-N‘-hydroxy-4-((2-methoxyethyl)amino)-1,2,5-oxadiazole-3-carboximidamide 
• 1204669-61-3 N-hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride 
• 1204669-60-2 N¹-hydroxy-4-((2-methoxyethyl)amino)-1,2,5-oxadiazole-3-carboximidamide 

Relevant articles and documents

Singlet molecular oxygen regulates vascular tone and blood pressure in inflammation

Singlet molecular oxygen (1O2) has well-established roles in photosynthetic plants, bacteria and fungi1–3, but not in mammals. Chemically generated 1O2 oxidizes the amino acid tryptophan to precursors of a key metabolite called N-formylkynurenine4, whereas enzymatic oxidation of tryptophan to N-formylkynurenine is catalysed by a family of dioxygenases, including indoleamine 2,3-dioxygenase 15. Under inflammatory conditions, this haem-containing enzyme is expressed in arterial endothelial cells, where it contributes to the regulation of blood pressure6. However, whether indoleamine 2,3-dioxygenase 1 forms 1O2 and whether this contributes to blood pressure control have remained unknown. Here we show that arterial indoleamine 2,3-dioxygenase 1 regulates blood pressure via formation of 1O2. We observed that in the presence of hydrogen peroxide, the enzyme generates 1O2 and that this is associated with the stereoselective oxidation of l-tryptophan to a tricyclic hydroperoxide via a previously unrecognized oxidative activation of the dioxygenase activity. The tryptophan-derived hydroperoxide acts in vivo as a signalling molecule, inducing arterial relaxation and decreasing blood pressure; this activity is dependent on Cys42 of protein kinase G1α. Our findings demonstrate a pathophysiological role for 1O2 in mammals through formation of an amino?acid-derived hydroperoxide that regulates vascular tone and blood pressure under inflammatory conditions.

Preparation method of IDO1 inhibitor Epacadostat intermediate

The invention relates to the drug synthesis field, specifically to a preparation method of an IDO1 (indoleamine-2, 3-dioxygenase 1) inhibitor Epacadostat intermediate 4-(3-bromo-4-fluorophenyl)-3-(4-((2-bromoethyl)amino)-1, 2, 5-oxadiazole-3-yl)-1, 2, 4-o

Synthetic method of IDO inhibitor Aikaduosita

The invention discloses a synthetic method of an IDO inhibitor Aikaduosita, and relates to the technical field of organic synthesis. The method comprises the following steps: carrying out an addition rearrangement reaction on N-Boc-ethylene diamine used as a raw material to obtain an intermediate 1, carrying out an acid deprotection reaction on the intermediate 1 to obtain an intermediate 2, carrying out a condensation reaction on the intermediate 2 and a compound 1 to obtain an intermediate 3, and carrying out an alkaline ring opening reaction on the intermediate 3 to finally prepare the IDO inhibitor Aikaduosita. Compared with reported methods, the method disclosed in the invention has the advantages of short route, high yield, simplicity in post-treatment, avoiding of explosive reagents and ultralow temperature conditions, small pollution, and suitableness for industrial production.