ChemicalBook > CAS DataBase List > N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide

N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide

Product Name: N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide
CAS No.: 726169-73-9
Chemical Name: N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide
Synonyms: Mocetinostat;MGCD0103;MG0103;CS-1929;Mocetinostat, >=98%;CD0103) Mocetinostat;MGCD0103(Mocetinostat);Mocetinostat (MGCD0103);Mocetinostat, 10 mM in DMSO;Mocetinostat (MGCD0103,MG0103)
CBNumber: CB42484945
Molecular Formula: C23H20N6O
Formula Weight: 396.44
MOL File: 726169-73-9.mol

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N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide Property

Melting point:: >170oC (dec.)
Density: 1.340±0.06 g/cm3(Predicted)
storage temp.: RT
solubility: Soluble in DMSO (up to 25 mg/ml)
pka: 13.13±0.70(Predicted)
form: solid
color: Off-white
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
InChI: InChI=1S/C23H20N6O/c24-19-5-1-2-6-21(19)28-22(30)17-9-7-16(8-10-17)14-27-23-26-13-11-20(29-23)18-4-3-12-25-15-18/h1-13,15H,14,24H2,(H,28,30)(H,26,27,29)
InChIKey: HRNLUBSXIHFDHP-UHFFFAOYSA-N
SMILES: C(NC1=CC=CC=C1N)(=O)C1=CC=C(CNC2=NC=CC(C3=CC=CN=C3)=N2)C=C1

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML3453
Product name: MGCD0103
Purity: ≥95% (HPLC)
Packaging: 10 mg
Price: $66.6
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML3453
Product name: MGCD0103
Purity: ≥95% (HPLC)
Packaging: 50 mg
Price: $268
Updated: 2025/07/31

Cayman Chemical

Product number: 18287
Product name: Mocetinostat
Purity: ≥98%
Packaging: 1mg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 18287
Product name: Mocetinostat
Purity: ≥98%
Packaging: 5mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 18287
Product name: Mocetinostat
Purity: ≥98%
Packaging: 10mg
Price: $172
Updated: 2024/03/01

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N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide Chemical Properties,Usage,Production

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.

Definition

ChEBI: N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide is a member of benzamides.

Synthesis

849235-68-3

95-54-5

726169-73-9

To a 2L three-necked round-bottomed flask equipped with a thermometer, a nitrogen introduction tube, a mechanical stirrer, and a dropping funnel was added 4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzoic acid (3.40 g, 0.131 mol), o-phenylenediamine (59.3 g, 0.548 mol), 1-hydroxybenzotriazole hydrate (HOBT) (21.7 g 0.156 mol) and DMSO (240 mL). Triethylamine (Et3N) (43.7 mL, 0.313 mol) was added to the stirring mixture at room temperature. The reaction mixture was stirred for 10 minutes, then a suspension of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl) (30.04 g, 0.156 mol) in DMSO (240 mL) was added in batches of three over 30 minutes at the same temperature. After addition, the reaction mixture was continued to be stirred for 20 h. (The progress of the reaction was monitored by NMR or HPLC to confirm complete consumption of 4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzoic acid). Upon completion of the reaction, 30% isopropanol (IPA) aqueous solution (800 mL) was added to the reaction mixture in three portions over 30 minutes. After addition, the reaction mixture formed a suspension, which was cooled to 0-5°C over 45 minutes and stirring was continued at the same temperature for 1 hour. The solid product was collected by diafiltration, washed with 30% aqueous IPA (400 mL) and dried over air to afford the crude product N-(2-aminophenyl)-4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzamide (43.04 g, 83% yield).

in vivo

Mocetinostat (MGCD0103) significantly inhibits growth of human tumor xenografts in nude mice in a dose-dependent manner and the antitumor activity correlated with induction of histone acetylation in tumors. The p.o. administration of Mocetinostat (MGCD0103) (2HBr salt) significantly reduces growth of implanted advanced A549 tumors in nude mice in a dose-dependent manner after 13 days of daily administration. Mocetinostat (170 mg/kg for 2HBr salt, corresponding to 120 mg/kg of free base) significantly blocks growth of tumors compared with vehicle treatment alone (P<0.05 in post-ANOVA Dunnett's test) with no change in body weight^[1].

target

HDAC1

IC 50

HDAC1: 0.15 μM (IC₅₀); HDAC2: 0.29 μM (IC₅₀); HDAC11: 0.59 μM (IC₅₀); HDAC3: 1.66 μM (IC₅₀)

References

[1] NANCY ZHOU. Discovery of N-(2-Aminophenyl)-4-[(4-pyridin-3-ylpyrimidin-2-ylamino)methyl]benzamide (MGCD0103), an Orally Active Histone Deacetylase Inhibitor[J]. Journal of Medicinal Chemistry, 2008, 51 14: 4072-4075. DOI:10.1021/jm800251w
[2] STÉPHANE RAEPPEL . SAR and biological evaluation of analogues of a small molecule histone deacetylase inhibitor N-(2-aminophenyl)-4-((4-(pyridin-3-yl)pyrimidin-2-ylamino)methyl)benzamide (MGCD0103)[J]. Bioorganic & Medicinal Chemistry Letters, 2009, 19 3: Pages 644-649. DOI:10.1016/j.bmcl.2008.12.048
[3] HIKMET NURAL-GUVENER. Anti-Fibrotic Effects of Class I HDAC Inhibitor, Mocetinostat Is Associated with IL-6/Stat3 Signaling in Ischemic Heart Failure.[J]. International Journal of Molecular Sciences, 2015, 16 5: 11482-11499. DOI:10.3390/ijms160511482
[4] FRANZISKA DENK . HDAC inhibitors attenuate the development of hypersensitivity in models of neuropathic pain[J]. PAIN®, 2013, 154 9: Pages 1668-1679. DOI:10.1016/j.pain.2013.05.021
[5] CLAIRE BONFILS. Evaluation of the pharmacodynamic effects of MGCD0103 from preclinical models to human using a novel HDAC enzyme assay.[J]. Clinical Cancer Research, 2008, 14 11: 3441-3449. DOI:10.1158/1078-0432.ccr-07-4427

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View Lastest Price from N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide manufacturers

Career Henan Chemical Co

Product: N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide 726169-73-9
Price: US $1.00/KG
Min. Order: 1G
Purity: 98%
Supply Ability: 100KG
Release date: 2018-08-21

726169-73-9, N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamideRelated Search:

ZM 336372 AG 490 17-AAG Troglitazone Acetanilide ACY-1215 Panobinostat JNJ-26481585 Vorinostat Belinostat (PXD101) Entinostat

MGCD0103

Mocetinostat

MGCD0103(Mocetinostat)

MG0103

Mocetinostat (MGCD0103,MG0103)

N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide

Mocetinostat (MGCD0103)

N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide Mocetinostat (MGCD0103)

Mocetinostat, >=98%

N-(2-Aminophenyl)-4-[[[4-(3-pyridyl)pyrimidin-2-yl]amino]methyl]benzamide

MGCD0103;MGCD 0103;MGCD-0103;MG0103

MGCD0103; MGCD 0103; MGCD-0103

CS-1929

Benzamide, N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]-

N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide USP/EP/BP

Mocetinostat, 10 mM in DMSO

CD0103) Mocetinostat

726169-73-9

C23H20ON6

Inhibitor

Inhibitors

API