Tacedinaline

Base Information

• Chemical Name: Tacedinaline
• CAS No.: 112522-64-2
• Molecular Formula: C15H14N2O2
• Molecular Weight: 269.303
• Hs Code.: 2924299090
• European Community (EC) Number: 631-226-3
• UNII: UMF554N5FG
• DSSTox Substance ID: DTXSID60150095
• Nikkaji Number: J545.180I
• Wikidata: Q27088920
• NCI Thesaurus Code: C2202
• Pharos Ligand ID: 7ZG3ZVF7ZDUP
• Metabolomics Workbench ID: 153307
• ChEMBL ID: CHEMBL235191
• Mol file: 112522-64-2.mol

Synonyms:4-acetylamino-N-(2'-aminophenyl)benzamide;acetyldinaline;CI 994;CI-994;GOE 5549;GOE-5549;PD 123654;PD-123654;tacedinaline

Chemical Property of Tacedinaline

Chemical Property:

• Appearance/Colour: white
• Melting Point: 216.1 °C
• Boiling Point: 450.6 °C at 760 mmHg
• PKA: 13.15±0.70(Predicted)
• Flash Point: 226.3 °C
• PSA: 84.22000
• Density: 1.322 g/cm³
• LogP: 3.20670
• Storage Temp.: Store at +4°C
• Sensitive.: Air Sensitive
• Solubility.: Soluble in DMSO
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 269.116426730
• Heavy Atom Count: 20
• Complexity: 351

Purity/Quality:

Tacedinaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)C(=O)NC2=CC=CC=C2N
• Recent ClinicalTrials: CI-994 in Treating Patients With Advanced Myeloma
• Description: CI-994 (112522-64-2) is an orally active histone deacetylase (HDAC) inhibitor, IC50 = 0.9, 0.9, 1.2 and >20 μM for HDAC1, HDAC2, HDAC3 and HDAC8 respectively.1 Mediates G1 cell cycle arrest, inhibits proliferation and induces apoptosis in vitro and in vivo.2,3 Increases neuroplasticity during memory extinction.4 Protects beta cells from cytokine-induced apoptosis.4
• Uses: Tacedinaline is a histone deacetylase (HDAC) inhibitor. Tacedinaline is an anti-cancer agent as HDAC inhibitors block angiogenesis, arrest cell growth, and lead to differentiation and apoptosis in tum or cells. Studies show Tacedinaline to be effective against acute myeloid leukemia in vitro and in vivo when used in combination with conventional anti-cancer agents. Tacedinaline is a histone deacetylase (HDAC) inhibitor. Tacedinaline is an anti-cancer agent as HDAC inhibitors block angiogenesis, arrest cell growth, and lead to differentiation and apoptosis in tumor cells. Studies show Tacedinaline to be effective against acute myeloid leukemia in vitro and in vivo when used in combination with conventional anti-cancer agents.

Technology Process of Tacedinaline

There total 12 articles about Tacedinaline 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: 97.0%

tert-butyl (2-(4-acetamidobenzamido)phenyl)carbamate (1299346-13-6) → CI-994 (112522-64-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/d0cc01485k

Reference yield: 92.0%

4-acetamido-N-(2-aminophenyl)benzamide trifluoroacetate salt (1353653-79-8) → CI-994 (112522-64-2)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; for 1.5h; pH=8;

Reference yield: 81.0%

p-(acetylamino)benzoic acid (556-08-1) + 1,2-diamino-benzene (95-54-5) → CI-994 (112522-64-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2008.07.048

upstream raw materials:

p-(acetylamino)benzoic acid

1,2-diamino-benzene

6-[2-(4-acetylamino-benzoylamino)-phenylcarbamoyloxy]-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylic acid

6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-tetrahydro-2H-pyran-2-carboxylic acid

Downstream raw materials:

3,4,5-triacetoxy-6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-tetrahydro-2H-pyran-2-carboxylic acid methyl ester

N-(2-{[4-(acetylamino)phenyl]carbonylamino}phenyl)-2-[(tert-butoxy)carbonylamino]acetamide

4-{[N-(2-{[4-{acetylamino}phenyl]carbonylamino}phenyl)carbamoyloxy]methyl}phenyl(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

(N-{[N-(2-{[4-(acetylamino)phenyl]carbonylamino}phenyl)-carbamoyl]methyl}carbamoyloxy)methyl(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Refernces

• 1、 -. "HDAC DEGRADER". . . Retrieved 2021/07/31.
• 2、 -. "NOVEL SOLID FORMS OF TACEDINALINE". Paragraph 0149; 0150. . Retrieved 2013/05/08.