Chidamide

Base Information

• Chemical Name: Chidamide
• CAS No.: 743420-02-2
• Molecular Formula: C22H19FN4O2
• Molecular Weight: 390.417
• UNII: 462284YV3M
• DSSTox Substance ID: DTXSID801348099
• Wikidata: Q27075960,Q76411459
• Pharos Ligand ID: GDXL2PSBTW5R
• ChEMBL ID: CHEMBL4087968
• Mol file: 743420-02-2.mol

Synonyms:chidamide;N-(2-amino-5-fluorobenzyl)-4-(N-(pyridine-3-acrylyl)aminomethyl)benzamide

Chemical Property of Chidamide

Chemical Property:

• Melting Point: >145°C (dec.)
• Boiling Point: 600.2±55.0 °C(Predicted)
• PKA: 12.30±0.70(Predicted)
• PSA: 97.11000
• Density: 1.336±0.06 g/cm3(Predicted)
• LogP: 4.42990
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 390.14920402
• Heavy Atom Count: 29
• Complexity: 577

Purity/Quality:

99% ^*data from raw suppliers

De-4-fluoro 5-Fluoro Chidamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CN=C1)C=CC(=O)NCC2=CC=C(C=C2)C(=O)NC3=C(C=CC(=C3)F)N
• Isomeric SMILES: C1=CC(=CN=C1)/C=C/C(=O)NCC2=CC=C(C=C2)C(=O)NC3=C(C=CC(=C3)F)N
• Recent ClinicalTrials: Treatment of Chidamide and Venetoclax for Retinoic Acid and Arsenic Resistant Acute Promyelocytic Leukemia
• Description: Chidamide (Epidaza?), a class I HDAC inhibitor, was discovered and developed by ChipScreen and approved by the CFDA in December 2014 for the treatment of recurrent of refractory peripheral T-cell lymphoma. Chidamide, also known as CS055 and HBI- 8000, is an orally bioavailable benzamide type inhibitor of HDAC isoenzymes class I 1–3, as well as class IIb 10, with potential antineoplastic activity. It selectively binds to and inhibits HDAC, leading to an increase in acetylation levels of histone protein H3.74 This agent also inhibits the expression of signaling kinases in the PI3K/ Akt and MAPK/Ras pathways and may result in cell cycle arrest and the induction of tumor cell apoptosis. Currently, phases I and II clinical trials are underway for the treatment of non-small cell lung cancer and for the treatment of breast cancer, respectively.
• Uses: De-5-fluoro 4-Fluorochidamide is an analogue of Chidamide (CAS 743420-02-0), a hitsone deacetylase inhibitor (HDACI) that enhances gemcitabine (G305000) cytotoxicity in pancreatic cancer cells.

Technology Process of Chidamide

There total 1 articles about Chidamide 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: 57.0%

4-fluoro-1,2-phenylenediamine (367-31-7) + 4-[N-(pyridin-3-ylacryloyl)aminomethyl]benzoic acid (219964-34-8) → N-(2-amino-5-fluorophenyl)-4-[N-(pyridin-3-ylacryloyl)aminomethyl]benzamide (743420-02-2)

Guidance literature:

4-[N-(pyridin-3-ylacryloyl)aminomethyl]benzoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 45 ℃; for 1h;

4-fluoro-1,2-phenylenediamine; With trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 24h;

upstream raw materials:

4-fluoro-1,2-phenylenediamine

4-[N-(pyridin-3-ylacryloyl)aminomethyl]benzoic acid

Refernces