(1S-endo)-5-(4-Chloro-3-methylphenyl)-1-((4-methylphenyl)methyl)-N-(1,3,3-trimethylbicyclo(2.2.1)hept-2-yl)-1H-pyrazole-3-carboxamide

Base Information

• Chemical Name: (1S-endo)-5-(4-Chloro-3-methylphenyl)-1-((4-methylphenyl)methyl)-N-(1,3,3-trimethylbicyclo(2.2.1)hept-2-yl)-1H-pyrazole-3-carboxamide
• CAS No.: 192703-06-3
• Molecular Formula: C29H34ClN3O
• Molecular Weight: 475.24
• DSSTox Substance ID: DTXSID50940947
• Nikkaji Number: J942.050I
• Wikipedia: SR-144,528
• Wikidata: Q7392759
• Pharos Ligand ID: Z21DCZMH51U6
• ChEMBL ID: CHEMBL381791
• Mol file: 192703-06-3.mol

Synonyms:N-(1,3,3-trimethylbicyclo(2.2.1)heptan-2-yl)-5-(4-chloro-3-methylphenyl)-1-(4-methylbenzyl)pyrazole-3-carboxamide;SR 144528;SR-144528;SR144528

Chemical Property of (1S-endo)-5-(4-Chloro-3-methylphenyl)-1-((4-methylphenyl)methyl)-N-(1,3,3-trimethylbicyclo(2.2.1)hept-2-yl)-1H-pyrazole-3-carboxamide

Chemical Property:

• Vapor Pressure: 1.14E-15mmHg at 25°C
• Refractive Index: 1.632
• Boiling Point: 627.699 °C at 760 mmHg
• Flash Point: 333.42 °C
• PSA: 46.92000
• Density: 1.222 g/cm³
• LogP: 7.20410
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 20 mg/ml, with warming).
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 475.2390404
• Heavy Atom Count: 34
• Complexity: 750

Purity/Quality:

98%,99%, ^*data from raw suppliers

SR144528 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)CN2C(=CC(=N2)C(=O)NC3C(C4CCC3(C4)C)(C)C)C5=CC(=C(C=C5)Cl)C
• Isomeric SMILES: CC1=CC=C(C=C1)CN2C(=CC(=N2)C(=O)N[C@H]3[C@]4(CC[C@H](C4)C3(C)C)C)C5=CC(=C(C=C5)Cl)C
• Description: SR 144528 is a cannabinoid (CB) receptor 2 inverse agonist with Ki values ranging from 0.3 to 5.6 nM. It is selective for CB2 over CB1 receptors, where it has Ki values ranging from 305 to >10,000 nM. SR 144528 blocks the inhibitory effects of CP 55,940 on forskolin-induced adenylyl cyclase activity in CHO cells expressing hCB2 (IC50 = 10 nM) but not in cells expressing hCB1 (IC50 = >10 μM). SR 144528 has been used to investigate the contribution of the CB2 receptor in the control of pain initiation as well as suppression of inflammation and immune activation.
• Uses: SR144528 has been used as a cannabinoid CB2 receptor antagonist:to study its blocking effect on the anti-dyskinetic functionality of HU-308to study its effects on spontaneous excitatory postsynaptic currents (sEPSCs) from the globus pallidus neuronsto analyze its effect on the gastric emptying in rats SR 144528 acts as a selective peripheral cannabinoid (CB2) receptor inverse agonist. Used in studies involving application of cannibis and anticancer drugs and multi-drug resistance (MDR) of the patie nt. SR 144528 acts as a selective peripheral cannabinoid (CB2) receptor inverse agonist. Used in studies involving application of cannabis and anticancer drugs and multi-drug resistance (MDR) of the patient.

Technology Process of (1S-endo)-5-(4-Chloro-3-methylphenyl)-1-((4-methylphenyl)methyl)-N-(1,3,3-trimethylbicyclo(2.2.1)hept-2-yl)-1H-pyrazole-3-carboxamide

There total 5 articles about (1S-endo)-5-(4-Chloro-3-methylphenyl)-1-((4-methylphenyl)methyl)-N-(1,3,3-trimethylbicyclo(2.2.1)hept-2-yl)-1H-pyrazole-3-carboxamide 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:

4-chloro-3-methylacetophenone (37074-39-8) → SR 144528 (192703-06-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium t-butoxide; lithium diisopropylamide / tetrahydrofuran; heptane; diethyl ether / 0.92 h / -78 °C

1.2: 68 percent / tetrahydrofuran; heptane; diethyl ether / 72 h / 20 °C

2.2: NaOH

3.1: SOCl₂

4.1: triethylamine

With thionyl chloride; potassium tert-butylate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; n-heptane;

DOI:10.1002/jlcr.952

Reference yield:

4-(4-chloro-3-methylphenyl)-2,4-dioxobutyric acid ethyl ester (475471-20-6) → SR 144528 (192703-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1.2: NaOH

2.1: SOCl₂

3.1: triethylamine

With thionyl chloride; triethylamine;

DOI:10.1002/jlcr.952

Reference yield:

5-(4-chloro-3-methyl-phenyl)-1-[(4-methylphenyl)methyl]-1H-pyrazole-3-carboxylic acid (192702-07-1) → SR 144528 (192703-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂

2: triethylamine

With thionyl chloride; triethylamine;

DOI:10.1002/jlcr.952

upstream raw materials:

1-(4-methylbenzyl)-5-(4-chloro-3-methylphenyl)pyrazole-3-carboxylic acid chloride

(1S)-endo-fenchylamine

4-(4-chloro-3-methylphenyl)-2,4-dioxobutyric acid ethyl ester

5-(4-chloro-3-methyl-phenyl)-1-[(4-methylphenyl)methyl]-1H-pyrazole-3-carboxylic acid

Refernces

• 1、 -. "3-pyrazolecarboxamide derivatives having cannabinoid receptor affinity". . . Retrieved 2008/06/13.