1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

Base Information

• Chemical Name: 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
• CAS No.: 183232-66-8
• Molecular Formula: C₂₂H₂₁Cl₂IN₄O
• Molecular Weight: 555.245
• European Community (EC) Number: 634-045-8
• UNII: 3I4FA44MAI
• DSSTox Substance ID: DTXSID7042695
• Nikkaji Number: J1.080.914B
• Wikipedia: AM-251_(drug)
• Wikidata: Q4652514
• Pharos Ligand ID: 612SFTNJ6RVA
• ChEMBL ID: CHEMBL285932
• Mol file: 183232-66-8.mol

Synonyms:AM 251;AM-251;AM251;N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamide;N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide

Chemical Property of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 195-196℃
• Refractive Index: 1.702
• PKA: 11.31±0.20(Predicted)
• PSA: 50.16000
• Density: 1.65 g/cm³
• LogP: 6.21860
• Storage Temp.: Store at RT
• Solubility.: DMSO: >10 mg/mL, soluble
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 554.01371
• Heavy Atom Count: 30
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

AM 251 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)I
• Description: AM251 is a cannabinoid 1 (CB1) receptor 1 antagonist. It binds to CB1 receptors in rat forebrain membrane preparations (Ki = 7.5 nM) and is selective over CB2 receptors in mouse spleen preparations (Ki = 2,290 nM) in radioligand binding assays. AM251 inhibits GTPγS binding induced by the CB receptor agonist CP 55,940 in HEK293 cells expressing human CB1 receptors (EC50 = 8 nM). AM251 (10 mg/kg) decreases immobility time in the forced swim test in wild-type but not CB1 receptor-deficient mice. It reduces fasting-induced food intake and body weight gain in mice when administered at a dose of 30 mg/kg. AM251 also induces GTPγS binding in HEK293 cells expressing the orphan receptor GPR55 (EC50 = 39 nM) and potentiates GABA-induced GABAA receptor currents (EC50 = 0.4 μM). It prevents TGF-β1-induced epithelial-to-mesenchymal transition (EMT), inhibits SMAD2/3 and p38 MAPK activation, and reduces the expression of EMT-related transcription factors in HK-2 renal tubule epithelial cells. AM251 induces cell cycle arrest at the G2/M phase and apoptosis in A375 human melanoma cells.
• Uses: AM251, a CB1 cannabinoid receptor antagonist, has been used in a study to determine its interaction with hippocampal neurons to enhance spatial memory in mice. Inhibitor of CB1 receptors. AM 251is a biarylpyrazole compound which has been considered for many years as the prototypical cannabinoid (CB) receptor antagonist

Technology Process of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

There total 14 articles about 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-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: 60.0%

C32H35Cl2GeN4O2Pol → 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide (183232-66-8)

Guidance literature:

With N-chloro-succinimide; acetic acid; trifluoroacetic acid; sodium iodide; In dichloromethane; at 20 ℃; for 1h; solid phase reaction;

DOI:10.1021/ol902038y

Reference yield:

2,4-dichlorophenyl hydrazine hydrochloride (5446-18-4) → 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide (183232-66-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) AcOH / 1.) EtOH, RT, 20 h, 2.) reflux, 24 h

3: 94 percent / N₂H₄ / Raney Ni / ethanol; H₂O / 3 h / 70 °C

4: 1.) aq. HCl, NaNO₂, 2.) aq. KI / 1.) 0 deg C, 10 min, 2.) RT, 4 h

With hydrogenchloride; acetic acid; potassium iodide; hydrazine; sodium nitrite; nickel; In ethanol; water;

DOI:10.1021/jm980363y

Reference yield:

1-phenyl-propan-1-one (93-55-0) → 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide (183232-66-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LiHMDS / 1.) hexane, diethyl ether, -78 deg C, 45 min, 2.) hexane, diethyl ether, RT, 16 h

2: 2.) AcOH / 1.) EtOH, RT, 20 h, 2.) reflux, 24 h

4: 94 percent / N₂H₄ / Raney Ni / ethanol; H₂O / 3 h / 70 °C

5: 1.) aq. HCl, NaNO₂, 2.) aq. KI / 1.) 0 deg C, 10 min, 2.) RT, 4 h

With hydrogenchloride; acetic acid; potassium iodide; lithium hexamethyldisilazane; hydrazine; sodium nitrite; nickel; In ethanol; water;

DOI:10.1021/jm980363y

upstream raw materials:

1-(2,4-dichlorophenyl)-5-(4-bromophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

5-(4-amino-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide

2,4-dichlorophenyl hydrazine hydrochloride

1-phenyl-propan-1-one

Downstream raw materials:

4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl nitrate

1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

Refernces

• 1、 Lan, Ruoxi,Liu, Qian,Fan, Pusheng,Lin, Sonyuan,Fernando, Susanthi R.,McCallion, Deirdre,Pertwee, Roger,Makriyannis, Alexandras. "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists". . p. 769 - 776. Retrieved 2007/10/03.