ACY-1215

Base Information

• Chemical Name: ACY-1215
• CAS No.: 1316214-52-4
• Molecular Formula: C24H27N5O3
• Molecular Weight: 433.51
• Hs Code.: 2933599090
• Mol file: 1316214-52-4.mol

Synonyms:N-[7-(Hydroxyamino)-7-oxoheptyl]-2-(N-phenylanilino)pyrimidine-5-carboxamide;

Chemical Property of ACY-1215

Chemical Property:

• PKA: 9.47±0.20(Predicted)
• PSA: 114.43000
• Density: 1.2±0.1 g/cm³
• LogP: 5.54720
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

2-(Diphenylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-5-pyrimidinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: ACY-1215 is an inhibitor of histone deacetylase 6 (HDAC6; IC50 = 5 nM). It is at least 10-fold less active against other HDACs in enzymatic assays. ACY-1215 shows synergistic activity with the proteasome inhibitor bortezomib against multiple myeloma (MM) cells, inducing protracted endoplasmic reticulum stress and apoptosis. ACY-1215 combined with proteasome inhibitors suppresses tumor growth and increases survival in mice with MM and mantle cell lymphoma xenografts. A multicenter phase I trial examining ACY-1215 combined with the E3 ligase inhibitor lenalidomide and dexamethasone in multiple myeloma found inhibition of HDAC6 in vivo. ACY-1215 also diminishes liver cyst development and fibrosis in a rat model of polycystic liver disease.
• Uses: This compound acts as a selective HDAC-6 (histone deacetylase) inihibitor. HDAC is linked to the transcription of DNA in cancers, including multiple myeloma (MM).

Technology Process of ACY-1215

There total 11 articles about ACY-1215 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: 48.0%

C25H28N4O3 (1316216-07-5) → N-[7-(hydroxyamino)-7-oxo-heptyl]-2-(N-phenylanilino)pyrimidine-5-carboxamide (1316214-52-4)

Guidance literature:

C₂₅H₂₈N₄O₃; With sodium hydroxide; In methanol; dichloromethane; at 0 ℃; for 0.166667h;

With hydroxylamine; In methanol; dichloromethane; water; at 0 - 20 ℃; for 0.333333h;

With hydrogenchloride; In water;

Reference yield:

ethyl 2-chloropyrimidine-5-carboxylate (89793-12-4) → N-[7-(hydroxyamino)-7-oxo-heptyl]-2-(N-phenylanilino)pyrimidine-5-carboxamide (1316214-52-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 120 °C

2.1: caesium carbonate / copper(l) iodide / tetraethoxy orthosilicate / 14 h / 140 °C

3.1: water / ethanol / 0.5 h / 60 °C

4.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C

5.1: sodium hydroxide / dichloromethane; methanol / 0.17 h / 0 °C

5.2: 0.33 h / 0 - 20 °C

With water; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; copper(l) iodide; In tetrahydrofuran; methanol; tetraethoxy orthosilicate; ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

aniline (62-53-3) → N-[7-(hydroxyamino)-7-oxo-heptyl]-2-(N-phenylanilino)pyrimidine-5-carboxamide (1316214-52-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 120 °C

2.1: caesium carbonate / copper(l) iodide / tetraethoxy orthosilicate / 14 h / 140 °C

3.1: water / ethanol / 0.5 h / 60 °C

4.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C

5.1: sodium hydroxide / dichloromethane; methanol / 0.17 h / 0 °C

5.2: 0.33 h / 0 - 20 °C

With water; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; copper(l) iodide; In tetrahydrofuran; methanol; tetraethoxy orthosilicate; ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

ethyl 2-chloropyrimidine-5-carboxylate

aniline

ethyl 2-(phenylamino)pyrimidine-5-carboxylate

C₁₉H₁₇N₃O₂

Refernces

• 1、 -. "PHARMACEUTICAL COMBINATIONS COMPRISING A HISTONE DEACETYLASE INHIBITOR AND EPOTHILONE AND METHODS OF USE THEREOF". . . Retrieved 2018/05/24.
• 2、 -. "PHARMACEUTICAL COMBINATIONS COMPRISING A HISTONE DEACETYLASE INHIBITOR AND A BCL-2 INHIBITOR AND METHODS OF USE THEREOF". . . Retrieved 2018/05/24.