Mocetinostat

Base Information

• Chemical Name: Mocetinostat
• CAS No.: 726169-73-9
• Molecular Formula: C23H20N6O
• Molecular Weight: 396.451
• Hs Code.: 2933990090
• European Community (EC) Number: 232-668-6
• UNII: A6GWB8T96J
• DSSTox Substance ID: DTXSID80222945
• Nikkaji Number: J2.554.200B
• Wikipedia: Mocetinostat
• Wikidata: Q424869
• NCI Thesaurus Code: C62521
• Pharos Ligand ID: CDVZ1TRTN8TM
• Metabolomics Workbench ID: 152924
• ChEMBL ID: CHEMBL272980
• Mol file: 726169-73-9.mol

Synonyms:MG 0103;MG 4230;MG 4915;MG 5026;MG-0103;MG-4230;MG-4915;MG-5026;MG0103;MG4230;MG4915;MG5206;MGCD 0103;MGCD-0103;MGCD0103;mocetinostat;N-(2-aminophenyl)-4-((4-pyridin-3-ylpyrimidin-2-ylamino)methyl)benzamide

Chemical Property of Mocetinostat

Chemical Property:

• Melting Point: >170oC (dec.)
• PKA: 13.13±0.70(Predicted)
• PSA: 105.82000
• Density: 1.341g/cm³
• LogP: 4.71240
• Storage Temp.: RT
• Solubility.: Soluble in DMSO (up to 25 mg/ml)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 396.16985928
• Heavy Atom Count: 30
• Complexity: 538

Purity/Quality:

99% ^*data from raw suppliers

Mocetinostat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Enzymes
• Canonical SMILES: C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC3=NC=CC(=N3)C4=CN=CC=C4
• Recent ClinicalTrials: Pembrolizumab (Immunotherapy Drug) in Combination With Guadecitabine and Mocetinostat (Epigenetic Drugs) for Patients With Advanced Lung Cancer.
• Recent EU Clinical Trials: A Phase 2, Randomized, Open-Label Study of Single Agent Azacitidine (Vidaza?) vs. Single Agent MGCD0103 vs. Azacitidine in Combination With MGCD0103 for the Treatment of Elderly Subjects With Newly Diagnosed Acute Myeloid Leukemia or Intermediate-2 or High-Risk Myelodysplastic Syndrome
• Description: Mocetinostat (726169-73-9) is a class I, isoform-selective HDAC inhibitor, IC50s=0.15, 0.29, 1.66 and 0.59 μM for HDAC1, 2, 3 and 11 respectively.1 Induces hyperacetylation of histones, induces expression of the tumor suppressor p21WAF1 and inhibits proliferation of human cancer cells.2 Mocetinostat displays antifibrotic effects in ischemic heart failure.3 Attenuates the development of hypersensitivity in models of neuropathic pain.4 Active in vivo.5
• Uses: Mocetinostat is a multi-targeted histone deacetylase inhibitor used in cancer therapy. Mocetinostat is undergoing clinical trials for the treatment of various cancers including follicular lymphoma, Hodgkin’s lymphoma and acute myelogenous leukemia.

Technology Process of Mocetinostat

There total 6 articles about Mocetinostat 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: 83.0%

4-(([4-(pyridin-3-yl)pyrimidin-2-yl]amino)methyl)benzoic acid (849235-68-3) + 1,2-diamino-benzene (95-54-5) → mocetinostat (726169-73-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dimethyl sulfoxide; at 20 ℃; for 20.6h; Solvent;

Reference yield: 66.0%

→ mocetinostat (726169-73-9)

Guidance literature:

Reference yield:

methyl 4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzoate (849235-67-2) → mocetinostat (726169-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hydroxide; water / 24 h / 20 °C

2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 24 h / 20 °C

With water; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; lithium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1021/jm400634n

upstream raw materials:

4-(([4-(pyridin-3-yl)pyrimidin-2-yl]amino)methyl)benzoic acid

1,2-diamino-benzene

methyl 4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzoate

4-guanidinomethylbenzoic acid methyl ester

Downstream raw materials:

N-(2-aminophenyl)-4-((4-(pyridin-3-yl)pyrimidin-2-ylamino)methyl)benzamide dihydrobromide

Refernces

• 1、 Marson, Charles M.,Matthews, Christopher J.,Yiannaki, Elena,Atkinson, Stephen J.,Soden, Peter E.,Shukla, Lena,Lamadema, Nermina,Thomas, N. Shaun B.. "Discovery of potent, isoform-selective inhibitors of histone deacetylase containing chiral heterocyclic capping groups and a N-(2-aminophenyl)benzamide binding unit". . p. 6156 - 6174. Retrieved 2013/09/02.
• 2、 -. "Inhibitors of histone deacetylase". . . Retrieved 2008/06/13.