1-(4-(Trifluoromethyl)benzyl)-3-(isoquinolin-5-yl)urea

Base Information

• Chemical Name: 1-(4-(Trifluoromethyl)benzyl)-3-(isoquinolin-5-yl)urea
• CAS No.: 581809-67-8
• Molecular Formula: C₁₈H₁₄F₃N₃O
• Molecular Weight: 345.324
• Hs Code.: 2933499090
• UNII: N2NOA4CE04
• DSSTox Substance ID: DTXSID20206906
• Nikkaji Number: J2.699.040H
• Wikidata: Q27074071
• Pharos Ligand ID: HUAVR3CN7H4T
• ChEMBL ID: CHEMBL104028
• Mol file: 581809-67-8.mol

Synonyms:1-isoquinolin-5-yl-3-(4-trifluoromethyl-benzyl)-urea;A-425619

Chemical Property of 1-(4-(Trifluoromethyl)benzyl)-3-(isoquinolin-5-yl)urea

Chemical Property:

• PSA: 57.51000
• LogP: 4.85270
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 345.10889656
• Heavy Atom Count: 25
• Complexity: 449

Purity/Quality:

95-99% ^*data from raw suppliers

A425619 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN=C2)C(=C1)NC(=O)NCC3=CC=C(C=C3)C(F)(F)F
• General Description: 1-(4-(Trifluoromethyl)benzyl)-3-(isoquinolin-5-yl)urea is a potent antagonist of the human vanilloid receptor 1 (VR1/TRPV1), developed from a high-throughput screening lead. It belongs to a class of N-isoquinolin-5-yl-N′-aralkyl ureas, which exhibit strong binding affinity and antagonistic activity against TRPV1, a target implicated in pain modulation. 1-(4-(TRIFLUOROMETHYL)BENZYL)-3-(ISOQUINOLIN-5-YL)UREA's structure-activity relationship (SAR) highlights the importance of the trifluoromethylbenzyl group for enhancing potency. This class of inhibitors represents a promising therapeutic approach for managing pain conditions mediated by TRPV1 activation.

Technology Process of 1-(4-(Trifluoromethyl)benzyl)-3-(isoquinolin-5-yl)urea

There total 5 articles about 1-(4-(Trifluoromethyl)benzyl)-3-(isoquinolin-5-yl)urea 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: 60.0%

isoquinolin-5-ylamine (1125-60-6) + 1-(isocyanatomethyl)-4-(trifluoromethyl)benzene (102422-55-9) → A-425619 (581809-67-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2004.04.038

Reference yield: 43.0%

p-Trifluoromethylbenzylamine (3300-51-4) + 2,2,2-trichloro-N-(isoquinolin-5-yl)acetamide (581812-64-8) → A-425619 (581809-67-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; Reflux;

DOI:10.2174/1573406415666190626130453

Reference yield:

isoquinolin-5-ylamine (1125-60-6) → A-425619 (581809-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

2: 41 percent / DBU / acetonitrile / 10 h / Heating

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jm0492958

upstream raw materials:

isoquinolin-5-ylamine

1-(isocyanatomethyl)-4-(trifluoromethyl)benzene

p-Trifluoromethylbenzylamine

2,2,2-trichloro-N-(isoquinolin-5-yl)acetamide