DGAT-1 inhibitor

Base Information

• Chemical Name: DGAT-1 inhibitor
• CAS No.: 959122-11-3
• Molecular Formula: C26H24N2O4
• Molecular Weight: 428.488
• Mol file: 959122-11-3.mol

Synonyms:DGAT-1Inhibitor 4a;Diacyl glycerolacyltransferase 1 inhibitor;A922500;

Chemical Property of DGAT-1 inhibitor

Chemical Property:

• Boiling Point: 576.1 °C at 760 mmHg
• Flash Point: 302.2 °C
• PSA: 95.50000
• Density: 1.323 g/cm³
• LogP: 5.82720
• Storage Temp.: Desiccate at +4°C
• Solubility.: ≥21.25 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

Purity/Quality:

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

A 922500 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-36-50
• Safety Statements: 26-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A922500 has been used in the inhibition of diacylglycerol acyltransferase (DGAT) in epithelial human breast cancer cell line (MDA-MB-231), digitonin-permeabilized human cancer cells, human myotubes and macrophages.

Technology Process of DGAT-1 inhibitor

There total 12 articles about DGAT-1 inhibitor 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-phenyl-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea (819056-67-2) + trans-(1R,2R)-2-(4-bromobenzoyl)cyclopentanecarboxylic acid (791594-13-3,1019115-10-6,733740-98-2) → (1R,2R)-2-[[4'-[(phenylamino)carbonyl]amino][1,1'-biphenyl-4-yl]carbonyl]cyclopentanecarboxylic acid (959122-11-3)

Guidance literature:

With dipotassium hydrogenphosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In ethanol; water; N,N-dimethyl-formamide; at 20 ℃; for 25h; Inert atmosphere;

DOI:10.1021/op900310v

Reference yield:

methyl cis-2-(4-bromobenzoyl)cyclopentanecarboxylate (791594-11-1) → (1R,2R)-2-[[4'-[(phenylamino)carbonyl]amino][1,1'-biphenyl-4-yl]carbonyl]cyclopentanecarboxylic acid (959122-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide

2: N-methyl-N-[(S)-1-phenylethyl]amine / Isopropyl acetate / 20 - 23 °C / Resolution of racemate

3: dipotassium hydrogenphosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / ethanol; water; N,N-dimethyl-formamide / 25 h / 20 °C / Inert atmosphere

With dipotassium hydrogenphosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); N-methyl-N-[(S)-1-phenylethyl]amine; sodium hydroxide; In ethanol; Isopropyl acetate; water; N,N-dimethyl-formamide; 3: Suzuki-Miyaura coupling;

DOI:10.1021/op900310v

Reference yield:

2-(4-bromobenzoyl)cyclohexan-1-one → (1R,2R)-2-[[4'-[(phenylamino)carbonyl]amino][1,1'-biphenyl-4-yl]carbonyl]cyclopentanecarboxylic acid (959122-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1: DBDMH; trifluoroacetic acid / acetonitrile / 17 h / 60 °C

2: potassium hydroxide / tetrahydrofuran; methanol; water / 46 h / 20 °C / Cooling

3: N-methyl-N-[(S)-1-phenylethyl]amine / Isopropyl acetate / 20 - 23 °C / Resolution of racemate

4: dipotassium hydrogenphosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / ethanol; water; N,N-dimethyl-formamide / 25 h / 20 °C / Inert atmosphere

With dipotassium hydrogenphosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); N-methyl-N-[(S)-1-phenylethyl]amine; DBDMH; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; Isopropyl acetate; water; N,N-dimethyl-formamide; acetonitrile; 2: Diketo Favorskii rearrangement / 4: Suzuki-Miyaura coupling;

DOI:10.1021/op900310v

upstream raw materials:

N-phenyl-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

trans-(1R,2R)-2-(4-bromobenzoyl)cyclopentanecarboxylic acid

methyl cis-2-(4-bromobenzoyl)cyclopentanecarboxylate

trans-(+/-)-2-(4-bromobenzoyl)cyclopentanecarboxylic acid

Refernces