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
More
Less

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
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

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
More
Less

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

N-(2-Aminophenyl)-4-([[4-(pyridin-3-yl)pyrimidin-2-yl]amino]methyl)benzamide Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

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

Canada 1 China 165 India 1 United Kingdom 2 United States 22 Global 191
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
ApexBio Technology LLC
Tel
+1-832-696-8203
Fax
+1-832-641-3177
Email
info@apexbt.com
Country
United States
ProdList
477
Advantage
60
Target molecule Corp.
Tel
857-239-0968
Fax
857-239-8801
Email
service1@targetmol.com
Country
United States
ProdList
2559
Advantage
60
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354; +17819995354
Email
marketing@targetmol.com
Country
United States
ProdList
32435
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Cckinase, Inc.
Tel
+1 (732)236-3202
Email
sales@cckinase.com
Country
United States
ProdList
2738
Advantage
58
Aladdin Scientific
Tel
Email
tp@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
LC Laboratories
Tel
--
Fax
--
Email
custserv@lclabs.com
Country
United States
ProdList
503
Advantage
50
Selleck Chemicals LLC
Tel
--
Fax
--
Email
info@selleckchem.com
Country
United States
ProdList
824
Advantage
60
Focus Biomolecules
Tel
--
Fax
--
Email
sales@focusbiomolecules.com
Country
United States
ProdList
1284
Advantage
58
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
Creative Enzymes
Tel
--
Fax
--
Email
info@creative-enzymes.com
Country
United States
ProdList
6057
Advantage
58
Axon Medchem LLC
Tel
--
Fax
--
Email
info@axonmedchem.com
Country
United States
ProdList
763
Advantage
58
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Alfa Chemistry
Tel
--
Fax
--
Email
info@Alfa-Chemistry.com
Country
United States
ProdList
6814
Advantage
0
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
ChemieTek
Tel
--
Fax
--
Email
info@chemietek.com
Country
United States
ProdList
219
Advantage
50
Exlcusive Chemistry Ltd
Tel
--
Fax
--
Country
United States
ProdList
446
Advantage
71
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
More
Less

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