1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea

Base Information

• Chemical Name: 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea
• CAS No.: 2089293-61-6
• Molecular Formula: C₂₃H₂₉Cl₂N₃O
• Molecular Weight: 434.409

Synonyms:

Chemical Property of 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

NAcM-OPT ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: NAcM-OPT (2089293-61-6) is a potent and selective NEDD8 ligation inhibitor, IC50=80 nM (in vitro).1? It inhibits the N-terminal acetyl-dependent interaction between the E2 conjugating enzyme UBE2M/UBC12 and DCN1, a subunit of a multiprotein E3 ligase for the ubiquitin-like protein NEDD8, an interaction which is essential for assembly of the multiprotein ligation complex.2 NAcM-OPT inhibits NEDD8 ligation in vitro and in cells (IC50=10 μM) and suppresses anchorage-independent growth of HCC95 cells and is highly selective with respect to other N-terminal acetyl protein binding sites.1
• Uses: NAcM-OPT inhibits N-Acetyl-mediated interaction between BE2M (E2 conjugating enzyme) and DCN1 (a component of E3 ligase complex). Also has inhibitory action on DCN2 and NEDD8 ubiquitin-like protein. Reduces anchorage-independent growth in DCN1-amplified cell line.

Technology Process of 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea

There total 3 articles about 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea 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:

1-n-butyl-4-piperidone (23081-86-9) → 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea (2089293-61-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 20 °C

2.1: tetrahydrofuran / 3 h / 20 °C

2.2: 16 h / 20 °C

With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.jmedchem.7b01282

Reference yield:

benzylamine (100-46-9) → 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea (2089293-61-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 20 °C

2.1: tetrahydrofuran / 3 h / 20 °C

2.2: 16 h / 20 °C

With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.jmedchem.7b01282

Reference yield:

N-benzyl-1-butylpiperidin-4-amine + m,p-dichloroaniline (95-76-1) + 1,1'-carbonyldiimidazole (530-62-1) → 1-benzyl-1-(1-butylpiperidin-4-yl)-3-(3,4-dichlorophenyl)urea (2089293-61-6)

Guidance literature:

m,p-dichloroaniline; 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 3h;

N-benzyl-1-butylpiperidin-4-amine; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.7b01282

upstream raw materials:

1-n-butyl-4-piperidone

m,p-dichloroaniline

1,1'-carbonyldiimidazole

benzylamine

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