3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate

Base Information

• Chemical Name: 3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate
• CAS No.: 546141-08-6
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.406
• Hs Code.: 2924299090
• European Community (EC) Number: 637-274-1
• UNII: PX47LB88FO
• DSSTox Substance ID: DTXSID70203046
• Nikkaji Number: J1.860.860J
• Wikipedia: URB597
• Wikidata: Q7865591
• Pharos Ligand ID: LSFRNDXVD7BZ
• ChEMBL ID: CHEMBL184238
• Mol file: 546141-08-6.mol

Synonyms:cyclohexyl carbamic acid 3'-carbamoylbiphenyl-3-yl ester;URB 597;URB-597;URB597

Chemical Property of 3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate

Chemical Property:

• Appearance/Colour: white powder
• Boiling Point: 533.2 °C at 760 mmHg
• PKA: 11.74±0.20(Predicted)
• Flash Point: 276.3 °C
• PSA: 81.42000
• Density: 1.23 g/cm³
• LogP: 4.96480
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~14 mg/mL, soluble
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 338.16304257
• Heavy Atom Count: 25
• Complexity: 462

Purity/Quality:

99.0% ^*data from raw suppliers

URB 597 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 22-24/25-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)NC(=O)OC2=CC=CC(=C2)C3=CC(=CC=C3)C(=O)N
• Recent ClinicalTrials: Evaluation Study of New Compounds With Potential Use in Schizophrenia
• Description: URB597 is a potent, orally bioavailable FAAH inhibitor with IC50 of 4.6 nM, with no activity on other cannabinoid-related targets. Phase 1. URB-597 (546141-08-6) is a potent and selective fatty acid amide hydrolase (FAAH) inhibitor, IC50 = 3-5 nM.1?Produces cannabinoid CB1 and CB2 receptor-mediated analgesia in inflammatory pain states without causing side effects associated with cannabinoid receptor activation.2?Attenuates the anxiolytic-like effect of acetaminophen in a mouse model.3?Exerts anti-inflammatory effects in rat hippocampus and ameliorates age-related deficits.4?Off target effects of URB-597: Reduces tyrosine hydroxylase expression.5 Improves cognitive?impairment caused by chronic cerebral hypoperfusion in a mouse model via inhibition of mTOR-dependent autophagy.6

Technology Process of 3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate

There total 5 articles about 3'-Carbamoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbamate 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: 51.0%

Cyclohexyl isocyanate (3173-53-3) + 3′-hydroxy-(1,1′-biphenyl)-3-carboxamide (681161-44-4) → URB597 (546141-08-6)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/jm301492y

Reference yield: 33.0%

Cyclohexyl isocyanide (931-53-3) + 3′-hydroxy-(1,1′-biphenyl)-3-carboxamide (681161-44-4) → URB597 (546141-08-6)

Guidance literature:

With triethylamine; In toluene; for 20h; Heating / reflux;

Reference yield:

3-bromobenzamide (22726-00-7) → URB597 (546141-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / aq. Na₂CO₃; Pd(PPh₃)4 / ethanol; toluene / 2 h / Heating

2: 33 percent / Et₃N / toluene / 18 h / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; triethylamine; In ethanol; toluene; 1: Suzuki cross-coupling;

DOI:10.1021/jm031140x

upstream raw materials:

Cyclohexyl isocyanate

3′-hydroxy-(1,1′-biphenyl)-3-carboxamide

cyclohexylamine

1,1'-carbonyldiimidazole

Refernces

• 1、 Wilson, Alan A.,Hicks, Justin W.,Sadovski, Oleg,Parkes, Jun,Tong, Junchao,Houle, Sylvain,Fowler, Christopher J.,Vasdev, Neil. "Radiosynthesis and evaluation of [11C-carbonyl ]-labeled carbamates as fatty acid amide hydrolase radiotracers for positron emission tomography". . p. 201 - 209. Retrieved 2013/03/14.
• 2、 -. "MODULATION OF ANXIETY THROUGH BLOCKADE OF ANANDAMIDE HYDROLYSIS". Page 59; 60 - 61. . Retrieved 2008/06/13.