N,N'-Dibenzylthiourea

Base Information

• Chemical Name: N,N'-Dibenzylthiourea
• CAS No.: 1424-14-2
• Deprecated CAS: 34853-56-0
• Molecular Formula: C15H16 N2 S
• Molecular Weight: 256.371
• Hs Code.: 2930909090
• European Community (EC) Number: 215-837-9
• NSC Number: 37141
• DSSTox Substance ID: DTXSID3061685
• Nikkaji Number: J12.279C
• Wikidata: Q81989597
• ChEMBL ID: CHEMBL1388908
• Mol file: 1424-14-2.mol

Synonyms:N,N'-Dibenzylthiourea;1,3-Dibenzylthiourea;1424-14-2;sym-Dibenzylthiourea;N,N-dibenzylthiourea;Thiourea, N,N'-bis(phenylmethyl)-;1,3-Dibenzyl-2-thiourea;Thiourea, bis(phenylmethyl)-;Urea, 1,3-dibenzyl-2-thio-;N,N/'-Dibenzylthiourea;DIBENZYLTHIOUREA;NSC 37141;CHEMBL1388908;EINECS 215-837-9;AI3-24936;NSC37141;Urea,3-dibenzyl-2-thio-;MLS000539149;SCHEMBL1275902;Thiourea,N'-bis(phenylmethyl)-;DTXSID3061685;HMS2504M08;BDBM50362770;MFCD00022013;NSC-37141;STK397440;AKOS000313277;NCGC00247275-01;SMR000160937;CS-0334155;FT-0629384;F87468;AB00527556-07;AN-689/40408316

Chemical Property of N,N'-Dibenzylthiourea

Chemical Property:

• Melting Point: 146-149oC
• Boiling Point: 405.4°Cat760mmHg
• Flash Point: 199°C
• PSA: 56.15000
• Density: 1.154g/cm³
• LogP: 3.63270
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 256.10341969
• Heavy Atom Count: 18
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

1,3-DIBENZYL-2-THIOUREA Aldrich ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 22-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=S)NCC2=CC=CC=C2
• General Description: N,N'-Dibenzylthiourea is a 1,3-diarylalkyl thiourea derivative that has been investigated as a potent TRPV1 antagonist, demonstrating significant activity in pain regulation. N,N'-DIBENZYLTHIOUREA's efficacy is optimized when it features a methylene linker between the thiourea core and the aromatic ring, along with a methanesulfonamido group at the 4-position of the benzene ring. Further enhancements in antagonistic activity are achieved by incorporating hydrogen-bond acceptors at the 3-position and appropriate hydrophobic substitutions. These structural modifications make N,N'-dibenzylthiourea a promising scaffold for developing advanced TRPV1-targeting therapeutics.

Technology Process of N,N'-Dibenzylthiourea

There total 53 articles about N,N'-Dibenzylthiourea 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: 100.0%

Benzyl isothiocyanate (622-78-6) + benzylamine (100-46-9) → dibenzyl thiourea (1424-14-2)

Guidance literature:

In hexane; at 20 ℃; for 2h;

DOI:10.2174/157017811797249281

Reference yield: 98.0%

Benzyl isothiocyanate (622-78-6) → dibenzyl thiourea (1424-14-2)

Guidance literature:

With water; triethylamine; In 1,4-dioxane; at 20 ℃; for 0.166667h;

DOI:10.1081/SCC-200061656

Reference yield: 95.0%

thiourea (17356-08-0) + benzylamine (100-46-9) → dibenzyl thiourea (1424-14-2)

Guidance literature:

With PEG-400; In water; for 0.00833333h; microwave irradiation;

DOI:10.1080/104265090968082

upstream raw materials:

1,2,3,4-thiatriazole-5-amine

benzylamine

4-methyl-pyrimidine-2-thione

Benzyl isothiocyanate

Downstream raw materials:

N-(phenylmethyl)acetamide

Benzyl isothiocyanate

S-(2-amino-ethyl)-N,N'-dibenzyl-isothiourea; dihydrobromide

5-benzylamino-1-benzyltetrazole

Refernces

Novel potent antagonists of transient receptor potential channel, vanilloid subfamily member 1: Structure-activity relationship of 1,3-diarylalkyl thioureas possessing new vanilloid equivalents

10.1021/jm0502790

The research aims to explore the structure-activity relationship (SAR) of a series of 1,3-dibenzyl thioureas as potential TRPV1 antagonists, which could be useful for pain regulation. The study systematically modulated three essential pharmacophoric regions of these compounds to identify potent TRPV1 antagonists. The researchers synthesized and tested multiple compounds, identifying six 1,3-dibenzyl thioureas with IC50 values between 10 and 100 nM in rat DRG neurons. The study concludes that the optimal linker between the thiourea and the aromatic part is methylene, and the methanesulfonamido group at the 4-position of the aromatic ring is crucial for high antagonistic activity. The introduction of H-bond acceptors at the 3-position and appropriate alkyl substitutions in the hydrophobic region C enhances activity. The findings provide a foundation for further development of advanced TRPV1 antagonists for clinical applications.