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1598383-40-4

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1598383-40-4 Usage

Description

The lysine methyltransferase EZH2 (KMT6), part of polycomb repressive complex 2, catalyzes trimethylation of lysine 27 on histone H3 and is involved in proliferation and aggressive cell growth associated with neoplastic cells. EPZ011989 is an orally bioavailable EZH2 inhibitor with Ki values that are less than 3 nM for wild type and Tyr646 mutated EZH2. It displays 15-fold selectivity for EZH2 over EZH1 and is without effect against an array of other lysine methyltransferases. EPZ011989 demonstrates significant tumor growth inhibition in a mouse xenograft model of human B cell lymphoma.

Uses

N-[(1,2-Dihydro-4,6-dimethyl-2-oxo-3-pyridinyl)methyl]-3-[ethyl[trans-4-[(2-methoxyethyl)methylamino]cyclohexyl]amino]-2-methyl-5-[3-(4-morpholinyl)-1-propyn-1-yl]-benzamide is used in biological studies as inhibitors of EZH2 histone methyltransferase for the treatment of cancer.

Check Digit Verification of cas no

The CAS Registry Mumber 1598383-40-4 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,5,9,8,3,8 and 3 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1598383-40:
(9*1)+(8*5)+(7*9)+(6*8)+(5*3)+(4*8)+(3*3)+(2*4)+(1*0)=224
224 % 10 = 4
So 1598383-40-4 is a valid CAS Registry Number.

1598383-40-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name EPZ 011989

1.2 Other means of identification

Product number -
Other names N-[(1,2-Dihydro-4,6-dimethyl-2-oxo-3-pyridinyl)methyl]-3-[ethyl[trans-4-[(2-methoxyethyl)methylamino]cyclohexyl]amino]-2-methyl-5-[3-(4-morpholinyl)-1-propyn-1-yl]benzamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1598383-40-4 SDS

1598383-40-4Synthetic route

3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one
771579-27-2

3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

C27H41N3O4
1598383-58-4

C27H41N3O4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Stage #1: 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one; C27H41N3O4 With triethylamine In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 0 - 20℃;
55.3%
Stage #1: 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one; C27H41N3O4 With triethylamine In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 0 - 20℃;
55.3%
methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-(ethyl)amino)-2-methylbenzoate
1403258-27-4

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-(ethyl)amino)-2-methylbenzoate

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C
1.2: 0 - 20 °C
2.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
3.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
4.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
5.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
6.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
6.2: 0 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N,N-dimethyl-formamide / 0.33 h / 0 °C
1.2: 0 - 20 °C
2.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
3.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
4.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
5.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
6.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
6.2: 0 - 20 °C
View Scheme
methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate
1598383-48-2

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
2.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
3.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
4.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
5.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
5.2: 0 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
2.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
3.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
4.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
5.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
5.2: 0 - 20 °C
View Scheme
methyl 5-bromo-3-(ethyl((trans)-4-(methylamino)cyclohexyl)amino)-2-methylbenzoate
1598383-55-1

methyl 5-bromo-3-(ethyl((trans)-4-(methylamino)cyclohexyl)amino)-2-methylbenzoate

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
2.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
3.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
4.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
4.2: 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
2.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
3.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
4.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
4.2: 0 - 20 °C
View Scheme
N-propargylmorpholine
5799-76-8

N-propargylmorpholine

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
2.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
3.2: 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
2.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
3.2: 0 - 20 °C
View Scheme
methyl 5-bromo-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methylbenzoate
1598383-56-2

methyl 5-bromo-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methylbenzoate

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
2.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
3.2: 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
2.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
3.2: 0 - 20 °C
View Scheme
methyl 3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzoate
1598383-57-3

methyl 3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzoate

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
2.2: 0 - 20 °C
View Scheme
2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: acetic acid / dichloromethane / 0.33 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: acetic acid / dichloromethane / 0.33 h / 20 °C
2.2: 16 h / 0 - 20 °C
3.1: N,N-dimethyl-formamide / 0.33 h / 0 °C
3.2: 0 - 20 °C
4.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
5.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
7.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
8.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
8.2: 0 - 20 °C
View Scheme
N-(tert-butoxycarbonyl)-4-aminocyclohexanone
179321-49-4

N-(tert-butoxycarbonyl)-4-aminocyclohexanone

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: acetic acid / dichloromethane / 0.33 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: acetic acid / dichloromethane / 0.33 h / 20 °C
2.2: 16 h / 0 - 20 °C
3.1: N,N-dimethyl-formamide / 0.33 h / 0 °C
3.2: 0 - 20 °C
4.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
5.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
7.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
8.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
8.2: 0 - 20 °C
View Scheme
methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-amino)-2-methylbenzoate
1403258-26-3

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-amino)-2-methylbenzoate

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
1598383-40-4

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: acetic acid / dichloromethane / 0.33 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: N,N-dimethyl-formamide / 0.33 h / 0 °C
2.2: 0 - 20 °C
3.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C
4.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C
5.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere
6.1: sodium hydroxide / water; ethanol / 1 h / 60 °C
7.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C
7.2: 0 - 20 °C
View Scheme

1598383-40-4Downstream Products

1598383-40-4Relevant articles and documents

EPZ011989, A potent, orally-available EZH2 inhibitor with robust in vivo activity

Campbell, John E.,Kuntz, Kevin W.,Knutson, Sarah K.,Warholic, Natalie M.,Keilhack, Heike,Wigle, Tim J.,Raimondi, Alejandra,Klaus, Christine R.,Rioux, Nathalie,Yokoi, Akira,Kawano, Satoshi,Minoshima, Yukinori,Choi, Hyeong-Wook,Porter Scott, Margaret,Waters, Nigel J.,Smith, Jesse J.,Chesworth, Richard,Moyer, Mikel P.,Copeland, Robert A.

, p. 491 - 495 (2015/05/27)

Inhibitors of the protein methyltransferase Enhancer of Zeste Homolog 2 (EZH2) may have significant therapeutic potential for the treatment of B cell lymphomas and other cancer indications. The ability of the scientific community to explore fully the spectrum of EZH2-associated pathobiology has been hampered by the lack of in vivo-active tool compounds for this enzyme. Here we report the discovery and characterization of EPZ011989, a potent, selective, orally bioavailable inhibitor of EZH2 with useful pharmacokinetic properties. EPZ011989 demonstrates significant tumor growth inhibition in a mouse xenograft model of human B cell lymphoma. Hence, this compound represents a powerful tool for the expanded exploration of EZH2 activity in biology.

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