N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea

Base Information

• Chemical Name: N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea
• CAS No.: 2301866-59-9
• Molecular Formula: C₂₃H₂₀Cl₂F₃N₅O₂S
• Molecular Weight: 558.411
• Mol file: 2301866-59-9.mol

Synonyms:

Chemical Property of N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea

Chemical Property:

• Boiling Point: 601.5±65.0 °C(Predicted)
• Density: 1.52±0.1 g/cm3(Predicted)

Purity/Quality:

99%+, ^*data from raw suppliers

DO-264 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DO264 is an inhibitor of α/β-hydrolase domain-containing protein 12 (ABHD12; IC50 = 11 nM). It inhibits ABHD12-dependent hydrolysis of lysophosphatidylserine (lyso-PS) in mouse brain membrane lysates (IC50 = 2.8 nM) and human THP-1 cells. DO264 increases levels of chemokine (C-C motif) ligand 3 (CCL3), CCL4, TNF-α, and IL-1β in M1-polarized THP-1 macrophages. It potentiates ferroptotic cell death induced by the glutathione peroxidase 4 (GPX4) inhibitor RSL3 in HT1080 fibrosarcoma and SU-DHL-5 B cell lymphoma cells when used at a concentration of 1 μM. In vivo, DO264 (30 mg/kg per day for four weeks) increases levels of 1-stearoyl-2-hydroxy-sn-glycero-3-PS, 1-arachidonoyl-2-hydroxy-sn-glycero-3-PS, 1-docosanoyl-2-hydroxy-sn-glycero-3-PS, 1-stearoyl-2-arachidonoyl-sn-glycero-3-PS, and 1-oleoyl-2-arachidonoyl-sn-glycero-3-PS in mouse brain. It increases levels of CCL2, CCL3, and CCL5 in bronchoalveolar lavage fluid (BALF) and decreases survival in a mouse model of infection with lymphocytic choriomeningitis virus (LCMV) clone 13 when administered at a dose of 30 mg/kg.
• Uses: DO264 is a potent inhibitor of ABHD12 (α/β-hydrolase domain-containing 12) which shows negligible interaction with other serine hydrolases as determined by activity-based protein profiling.

Technology Process of N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea

There total 6 articles about N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea 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:

pyridin-3-yl isothiocyanate (17452-27-6) + 1-(3-chloro-4-(2-chloro-4-(trifluoromethoxy)phenoxy)pyridin-2-yl)piperidin-4-ylamine → N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea (2301866-59-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/acs.jmedchem.8b01958

Reference yield:

tert-butyl (1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)carbamate → N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea (2301866-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

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

DOI:10.1021/acs.jmedchem.8b01958

Reference yield:

4-(trifluoromethoxy)-2-chlorophenol (70783-75-4) → N-3-pyridyl-N’-(1-[3-chloro-4-{2-chloro-4-(trifluoromethoxy)phenoxy}pyridine-2-yl]piperidin-4-yl)thiourea (2301866-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 - 20 °C

1.2: 90 - 100 °C

2.1: potassium carbonate / dimethyl sulfoxide / 100 - 120 °C

3.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With hydrogenchloride; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.8b01958

upstream raw materials:

pyridin-3-yl isothiocyanate

4-(trifluoromethoxy)-2-chlorophenol

2,3,4-trichloropyridine

Refernces

• 1、 -. "ABHD12 INHIBITORS AND METHODS OF MAKING AND USING SAME". Paragraph 00119; 00128. . Retrieved 2019/12/04.