5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole

Base Information

• Chemical Name: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole
• CAS No.: 611207-11-5
• Molecular Formula: C20H20Cl3N3
• Molecular Weight: 408.75
• European Community (EC) Number: 804-240-4
• DSSTox Substance ID: DTXSID20436100
• Nikkaji Number: J2.738.604K
• Wikidata: Q82251308
• ChEMBL ID: CHEMBL328379
• Mol file: 611207-11-5.mol

Synonyms:611207-11-5;LH 21;5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole;LH-21;CHEMBL328379;LH21;SCHEMBL3188922;DTXSID20436100;USJFDADYVUDVAX-UHFFFAOYSA-N;BDBM50147009;HY-121827;CS-0083509;5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-3-hexyl-1H-[1,2,4]triazole;5-(4-chlorophenyl)-1-(2,4-dichloro-phenyl)-3-hexyl-1h-1,2,4-triazole

Chemical Property of 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole

Chemical Property:

• PSA: 30.71000
• LogP: 7.01730
• Solubility.: ≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide
• XLogP3: 8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 407.072281
• Heavy Atom Count: 26
• Complexity: 417

Purity/Quality:

≥98% ^*data from raw suppliers

LH-21 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1=NN(C(=N1)C2=CC=C(C=C2)Cl)C3=C(C=C(C=C3)Cl)Cl
• Description: LH 21 is a 1,2,4-triazole that acts as a cannabimimetic. It has a relatively low-affinity for the central cannabinoid (CB1) receptor (Ki = 855 nM). However, it interferes, at low nanomolar concentrations, with the action of the potent CB1 agonist WIN 55,212-2 on murine vas deferens, suggesting that LH 21 acts as a silent CB1 antagonist. Consistent with this interpretation, LH 21 diminishes the in vivo effects of WIN 55,212-2 on standard CB tetrad responses in mice and reduces food intake and body weight gain in obese Zucker rats. However, in CHO cells overexpressing CB1, LH 21 is able to elevate cAMP, suggesting that, in this model, it acts as an inverse agonist of CB1. Furthermore, LH 21 suppresses food intake and body weight gain in both wild-type and CB1 receptor knockout mice, indicating that this receptor is not necessary for these effects.

Technology Process of 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole

There total 5 articles about 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole 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: 50.0%

N-heptanoyl-4-chlorobenzamide (39549-66-1) + 2,4-dichlorophenyl hydrazine hydrochloride (5446-18-4) → LH-21 (611207-11-5)

Guidance literature:

With pyridine; at 200 ℃; for 0.0166667h; regioselective reaction; Microwave irradiation;

DOI:10.1016/j.tet.2012.01.003

Reference yield: 9.0%

N-heptanoyl-4-chlorobenzamide (39549-66-1) + (2,4-dichlorophenyl)hydrazine (13123-92-7) → LH-21 (611207-11-5)

Guidance literature:

With sodium acetate; In acetic acid; for 22h; Heating;

DOI:10.1021/jm031099y

Reference yield:

n-heptanoic anhydride (626-27-7) → LH-21 (611207-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / H₂SO₄ / toluene / 1 h / Heating

2: 9 percent / NaOAc / acetic acid / 22 h / Heating

With sulfuric acid; sodium acetate; In acetic acid; toluene;

DOI:10.1021/jm031099y

upstream raw materials:

N-heptanoyl-4-chlorobenzamide

(2,4-dichlorophenyl)hydrazine

n-heptanoic anhydride

4-chlorobenzamide

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