nutlin-3A

Base Information

• Chemical Name: nutlin-3A
• CAS No.: 675576-98-4
• Molecular Formula: C₃₀H₃₀Cl₂N₄O₄
• Molecular Weight: 581.499
• European Community (EC) Number: 809-614-0
• UNII: 53IA0V845C,L7C92IOE65
• ChEMBL ID: CHEMBL191334
• DSSTox Substance ID: DTXSID801317967
• Metabolomics Workbench ID: 56689
• NCI Thesaurus Code: C74594
• Nikkaji Number: J2.492.420C
• Pharos Ligand ID: 2WF5UMQ1Y3G2,2WF65BJ3T7HM
• Wikidata: Q27166862
• Mol file: 675576-98-4.mol

Synonyms:nutlin 3;nutlin-3;nutlin-3A;nutlin-3B

Chemical Property of nutlin-3A

Chemical Property:

• PKA: 14.35±0.20(Predicted)
• PSA: 83.47000
• Density: 1.36
• LogP: 5.52600
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble5mg/mL, clear
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 580.1644108
• Heavy Atom Count: 40
• Complexity: 919

Purity/Quality:

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

Nutlin-3A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC1=C(C=CC(=C1)OC)C2=NC(C(N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl
• Isomeric SMILES: CC(C)OC1=C(C=CC(=C1)OC)C2=N[C@H]([C@H](N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl
• Uses: (ndash)-Nutlin-3 is an inhibitor of p-53-MDM2 interaction. Anti-cancer agent. Nutlin-3a has been used as a tumor suppressor p53(TP53) stabilizer and as an inhibitor of the mouse double minute 2 homolog (MDM2)–p53 interaction.

Technology Process of nutlin-3A

There total 23 articles about nutlin-3A 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: 89.0%

N-((1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethyl)-3-oxopiperazine-1-carboxamide (1353891-93-6) → nutlin-3a (548472-68-0,675576-98-4)

Guidance literature:

With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide; In dichloromethane; for 1.5h; Cooling with ice; Inert atmosphere;

DOI:10.1021/jo401321a

Reference yield:

4-chlorophenylnitromethane (29559-24-8) → nutlin-3a (548472-68-0,675576-98-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: H,⁽⁴⁾pyrrolidine(6,7)(MeO)2Quin-BAM / toluene / 24 h / -78 °C

2.1: sodium tetrahydroborate; methanol / cobalt(II) chloride / 1 h / 0 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dmap / dichloromethane / 16 h / 0 - 20 °C

4.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

5.1: 1,1'-carbonyldiimidazole / dichloromethane / 1.5 h / 20 °C

5.2: 15 h

6.1: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 1 h / 0 °C

With methanol; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,1'-carbonyldiimidazole; trifluoroacetic acid; Triphenylphosphine oxide; dmap; H,⁽⁴⁾pyrrolidine(6,7)(MeO)2Quin-BAM; cobalt(II) chloride; In dichloromethane; toluene;

Reference yield:

tert-butyl ((1R,2S)-2-amino-1,2-bis(4-chlorophenyl)ethyl)carbamate (1353891-88-9) → nutlin-3a (548472-68-0,675576-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dmap / dichloromethane / 16 h / 0 - 20 °C

2.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1.5 h / 20 °C

3.2: 15 h

4.1: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 1 h / 0 °C

With trifluoromethylsulfonic anhydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,1'-carbonyldiimidazole; trifluoroacetic acid; Triphenylphosphine oxide; dmap; In dichloromethane;

upstream raw materials:

4-methoxysalicylic acid

4-chlorobenzyl bromide

4-chlorophenylnitromethane

tert-butyl 4-chlorobenzylidenecarbamate

Refernces

• 1、 -. "ARYL-SUBSTITUTED IMIDAZOLES AND METHODS OF MAKING AND USING SAME". Paragraph 00451. . Retrieved 2015/12/17.
• 2、 Qin, Lingyun,Yang, Fei,Zhou, Cindy,Chen, Yao,Zhang, Huashan,Su, Zhengding. "Efficient reactivation of p53 in cancer cells by a dual MdmX/Mdm2 inhibitor". . p. 18023 - 18033. Retrieved 2015/03/03.