Vorinostat supplier | CasNO.149647-78-9

Name
Vorinostat
EINECS 682-505-1
CAS No. 149647-78-9
Article Data39
CAS DataBase
Density 1.174 g/cm³
Solubility
Melting Point 161-162 °C
Formula C₁₄H₂₀N₂O₃
Boiling Point
Molecular Weight 264.324
Flash Point
Transport Information
Appearance white crystalline solid
Safety 53-36/37-45
Risk Codes 61-68
Molecular Structure
Hazard Symbols T
Synonyms Octanediamide,N-hydroxy-N'-phenyl- (9CI);N-Hydroxy-N'-phenyloctanediamide;SAHA;Suberoylanilide hydroxamic acid;Zolinza;CCRIS 8456;M344;SAHA cpd;Suberanilohydroxamic acid;UNII-58IFB293JI;
PSA 78.43000
LogP 2.93500

Synthetic route

: 162853-41-0
7-phenylcarbamoyl heptanoic acid methyl ester

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Stage #1: 7-phenylcarbamoyl heptanoic acid methyl ester With hydroxylamine hydrochloride; sodium methylate In methanol; water for 16.1667h; Stage #2: With water; acetic acid In methanol for 0.166667h; pH=8.7 - 12.02;	95.6%
With hydroxylamine hydrochloride; sodium methylate In methanol for 16.1667h;	95.6%
Stage #1: 7-phenylcarbamoyl heptanoic acid methyl ester With hydroxylamine hydrochloride; sodium methylate In methanol for 16.3333h; Stage #2: With sodium methylate In methanol; water for 0.166667h; pH=12.01 - 12.02; Stage #3: With acetic acid In methanol; water pH=8.70 - 8.98; Product distribution / selectivity;	95.6%

: C21H24N2O3

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With 10 wt% Pd(OH)2 on carbon; hydrogen; trifluoroacetic acid In methanol at 20℃; for 2h;	91%

: 6998-10-3
N-phenylhexanamide

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In N,N-dimethyl-formamide at 40℃; for 1h; Reagent/catalyst;	88.5%

: 149647-86-9
8-(hydroxyamino)-8-oxooctanoic acid

: 62-53-3
aniline

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide; potassium hydroxide In ethanol at 50℃; for 0.5h;	82.4%
With dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole In tetrahydrofuran

: 149648-52-2
suberanilic acid

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With C36H24B4N2O3; hydroxylamine hydrochloride; triethylamine In toluene at 80℃; for 14h; Molecular sieve;	82%
Stage #1: suberanilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 0.5h; Stage #2: With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h;	75%
Stage #1: suberanilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 0.5h; Stage #2: With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h;	75%

: 162853-41-0
7-phenylcarbamoyl heptanoic acid methyl ester

A: 149648-52-2
suberanilic acid

B: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With water; hydroxylamine; sodium methylate In methanol at 90℃;	A 15% B 80%

: C17H23NO5

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With hydroxylamine In methanol
With hydroxylamine hydrochloride; potassium hydroxide In methanol at 20℃; for 0.25h;
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 3: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry 4: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C View Scheme
With hydroxylamine hydrochloride In tetrahydrofuran; methanol at 20℃; for 1.5h;
With hydroxylamine hydrochloride; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 0.5h;	0.14 g

: 3946-32-5
suberic acid monomethyl ester

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88.7 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 1.5 h / 20 °C 2: 90 percent / hydroxylamine; KOH / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 3 h / Reflux 2: triethylamine / dichloromethane / 1.5 h / 20 °C 3: hydroxylamine hydrochloride; sodium methylate / methanol / 0.67 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1-hydroxy-1H-benzotriazole hydrate / N,N-dimethyl-formamide 2: potassium hydroxide; hydroxylamine hydrochloride / methanol View Scheme
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dichloromethane / 20 °C / Cooling with ice 2.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice 3.2: 20 °C 4.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4 View Scheme

: 62-53-3
aniline

[(Xantphos)2Pd(3-methyl-1-butenyl]OTf: [(Xantphos)2Pd(3-methyl-1-butenyl]OTf

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88.7 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 1.5 h / 20 °C 2: 90 percent / hydroxylamine; KOH / methanol / 1 h / 20 °C View Scheme

: 505-48-6
octane-1,8-dioic acid

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / Ac2O / 1 h / Heating 2: 94 percent / tetrahydrofuran / 0.5 h / 20 °C 3: Et3N / tetrahydrofuran / 0.17 h 4: NH2OH / methanol View Scheme
Multi-step reaction with 6 steps 1.1: 0.17 h / 150 - 180 °C 1.2: 0.33 h / 20 °C 2.1: triethylamine / tetrahydrofuran / 0.25 h / -10 °C 3.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry 6.1: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 0.17 h / 185 - 190 °C / Sealed tube 2: Dowex50W-X2 acid resin / 22 h / Reflux 3: methanol; hydroxylamine hydrochloride; sodium View Scheme
Multi-step reaction with 3 steps 1.1: 0.33 h / 175 - 190 °C 1.2: 0.33 h 2.1: 18 h / Heating / reflux 3.1: hydroxylamine hydrochloride; sodium methylate / methanol View Scheme
Multi-step reaction with 3 steps 1.1: acetic anhydride 2.1: tetrahydrofuran 3.1: triethylamine; chloroformic acid ethyl ester / 0 °C 3.2: 20 °C View Scheme

: 10521-06-9
oxonane-2,9-dione

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / tetrahydrofuran / 0.5 h / 20 °C 2: Et3N / tetrahydrofuran / 0.17 h 3: NH2OH / methanol View Scheme
Multi-step reaction with 3 steps 1: copper(l) iodide / 1,4-dioxane; water 2: zinc(II) chloride / 3 h / 50 °C 3: sodium methylate; hydroxylamine hydrochloride / methanol / 3 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran 2.1: triethylamine; chloroformic acid ethyl ester / 0 °C 2.2: 20 °C View Scheme

: C16H21NO5

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With hydroxylamine In tetrahydrofuran; methanol at 0 - 5℃; for 0.25h;

: 505-48-6
octane-1,8-dioic acid

: 62-53-3
aniline

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With hydroxylamine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole In tetrahydrofuran at 25 - 30℃;
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole / tetrahydrofuran 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 25 - 30 °C 2.2: 0.5 h View Scheme
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate / tetrahydrofuran / 1 h / 0 - 5 °C 2.1: dmap; N-ethyl-N,N-diisopropylamine; ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate / tetrahydrofuran / 0.5 h / 0 - 5 °C 2.2: 20 °C View Scheme

: 3946-32-5
suberic acid monomethyl ester

: 62-53-3
aniline

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.08 h 1.2: 4 h / 25 °C 2.1: hydroxylamine hydrochloride; potassium hydroxide / methanol / 0.1 h / 80 °C / Microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: boric acid / toluene / 10 h / Reflux; Dean-Stark; Inert atmosphere; Green chemistry 2: potassium hydroxide; hydroxylamine hydrochloride / methanol / 0.5 h / 20 - 40 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C 2: hydroxylamine; potassium hydroxide / methanol / 1.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: boric acid / toluene / 10 h / Reflux; Inert atmosphere; Dean-Stark; Green chemistry 2: potassium hydroxide; hydroxylamine hydrochloride / methanol / 1 h / 40 °C / Green chemistry View Scheme

: 8-oxo-N-phenyloctanamide

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry 2: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C View Scheme

: 8-hydroxy-N-phenyloctanamide

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 2: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry 3: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; potassium permanganate / water / 20 °C 2.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / 0 °C 2.2: 1 h / 20 °C View Scheme

: 62-53-3
aniline

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 0.17 h / 150 - 180 °C 1.2: 0.33 h / 20 °C 2.1: triethylamine / tetrahydrofuran / 0.25 h / -10 °C 3.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry 6.1: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: copper(l) iodide / 1,4-dioxane; water 2: zinc(II) chloride / 3 h / 50 °C 3: sodium methylate; hydroxylamine hydrochloride / methanol / 3 h / 40 °C View Scheme
Multi-step reaction with 3 steps 1.1: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / 24 h / 100 °C 2.1: sodium hydroxide; potassium permanganate / water / 20 °C 3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / 0 °C 3.2: 1 h / 20 °C View Scheme

: diisopropyl 1-(8-oxo-8-(phenylamino)octanoyl)hydrazine-1,2-dicarboxylate

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 24h;

: 5698-29-3
oxonan-2-one

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / 24 h / 100 °C 2.1: sodium hydroxide; potassium permanganate / water / 20 °C 3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / 0 °C 3.2: 1 h / 20 °C View Scheme

: (4-(((8-oxo-8-(phenylamino)octanamido)oxy)methyl)phenyl)boronic acid

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With dihydrogen peroxide In aq. phosphate buffer at 37℃; for 4h; pH=7.4; Reagent/catalyst;

: (4-(((8-oxo-8-(phenylamino)octanamido)oxy)methyl)phenyl)boronic acid

A: C21H26N2O4

B: 149647-78-9
vorinostat

Conditions

Conditions	Yield
With dihydrogen peroxide In aq. phosphate buffer at 37℃; for 4h; pH=7.4; Reagent/catalyst;

: 62-53-3
aniline

A: C21H26N2O4

B: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dichloromethane / 20 °C / Cooling with ice 2.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice 3.2: 20 °C 4.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4 View Scheme

Yield

Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dichloromethane / 20 °C / Cooling with ice
2.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C
3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice
3.2: 20 °C
4.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4
View Scheme

: 3946-32-5
suberic acid monomethyl ester

A: C21H26N2O4

B: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dichloromethane / 20 °C / Cooling with ice 2.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice 3.2: 20 °C 4.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4 View Scheme

Yield

: 162853-41-0
7-phenylcarbamoyl heptanoic acid methyl ester

A: C21H26N2O4

B: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice 2.2: 20 °C 3.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4 View Scheme

: 149648-52-2
suberanilic acid

A: C21H26N2O4

B: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice 1.2: 20 °C 2.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4 View Scheme

: N-phenylhept-6-enamide

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 3 h / Reflux; Inert atmosphere 2: 10 wt% Pd(OH)2 on carbon; trifluoroacetic acid; hydrogen / methanol / 2 h / 20 °C View Scheme

: (E)-methyl 8-(benzyloxyamino)-8-oxooct-6-enoate

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: 10 wt% Pd(OH)2 on carbon; trifluoroacetic acid; hydrogen / methanol / 2 h / 20 °C View Scheme

: 1745-17-1
methyl hept-6-enoate

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 3 h / Reflux; Inert atmosphere 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: 10 wt% Pd(OH)2 on carbon; trifluoroacetic acid; hydrogen / methanol / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 3 h / Reflux; Inert atmosphere
2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: 10 wt% Pd(OH)2 on carbon; trifluoroacetic acid; hydrogen / methanol / 2 h / 20 °C
View Scheme

: C15H19NO4

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C 1.2: 16 h / 0 - 20 °C 2.1: 10 wt% Pd(OH)2 on carbon; trifluoroacetic acid; hydrogen / methanol / 2 h / 20 °C View Scheme

: 149647-78-9
vorinostat

: suberoylanilide hydroxamic acid iron complex

Conditions

Conditions	Yield
With iron(III) chloride; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 16.0833h;	96%

: 103-71-9
phenyl isocyanate

: 149647-78-9
vorinostat

: [(8-anilino-8-oxo-octanoyl)amino] N-phenylcarbamate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; acetone at -15 - 20℃;	96%

: 3173-56-6
benzyl isothiocyanate

: 149647-78-9
vorinostat

: [(8-anilino-8-oxo-octanoyl)amino] N-benzylcarbamate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; acetone at -15 - 20℃;	94%

: 149647-78-9
vorinostat

: 1795-48-8
Isopropyl isocyanate

: [(8-anilino-8-oxo-octanoyl)amino] N-isopropylcarbamate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; acetone at -15 - 20℃;	93%

: 149647-78-9
vorinostat

: 109-90-0
ethyl isocyanate

: [(8-anilino-8-oxo-octanoyl)amino] N-ethylcarbamate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; acetone at -15 - 20℃;	92%

: C44H74ClN3O11Si3

: 149647-78-9
vorinostat

: C58H93N5O14Si3

Conditions

Conditions	Yield
With pyridine at 0 - 25℃; for 5h;	92%

: 149647-78-9
vorinostat

: 637330-41-7
N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

: C58H91N5O15Si3

Conditions

Conditions	Yield
In pyridine at 0 - 25℃; for 5h;	92%
With pyridine at 0 - 20℃; for 5h;	85%

: 942428-83-3
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

: 149647-78-9
vorinostat

: 2,3,4,6-tetra-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20 - 20℃;	90%

: 942428-90-2
2,3,4,6-tetra-O-acetyl-D-mannopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

: 149647-78-9
vorinostat

: 2,3,4,6-tetra-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-α-D-mannopyranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20 - 20℃;	84%

: 55715-03-2
4-bromomethyl-3-nitrobenzoic acid

: 149647-78-9
vorinostat

: C22H25N3O7

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 18h;	83%

: N1,N2-dimethyl-N1-(2-phenylcyclopropyl)ethane-1,2-diamine dihydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

: 149647-78-9
vorinostat

: N1-((methyl(2-(methyl(2-phenylcyclopropyl)amino)ethyl)carbamoyl)oxy)-N8-phenyloctanediamide

Conditions

Conditions	Yield
Stage #1: 1,1'-carbonyldiimidazole; vorinostat In acetonitrile at 10℃; for 0.333333h; Stage #2: N1,N2-dimethyl-N1-(2-phenylcyclopropyl)ethane-1,2-diamine dihydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h;	82.7%

...Expand

: 6232-88-8
4-bromomethylbenzoic Acid

: 149647-78-9
vorinostat

: C22H26N2O5

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 18h;	79%

: 149647-78-9
vorinostat

: N-[(8-anilino-8-oxooctanoyl)oxy]-N'-phenyloctanediamide

Conditions

Conditions	Yield
Stage #1: suberanilic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) for 0.0833333h; Stage #2: vorinostat In DMF (N,N-dimethyl-formamide) for 24h;	77%

: 869996-05-4
O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate

: 149647-78-9
vorinostat

: 931415-42-8
methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20 - 20℃;	76%

: 2-(bromomethyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

: 149647-78-9
vorinostat

: N1-phenyl-N8-((2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methoxy)octanediamide

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 18h; Inert atmosphere;	74%

: 149647-78-9
vorinostat

: 100-46-9
benzylamine

: 1200803-45-7
C21H27N3O2

Conditions

Conditions	Yield
Stage #1: vorinostat With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine In dichloroethane at 0℃; for 1.5h; Lossen rearrangement; Inert atmosphere; Stage #2: benzylamine In dichloroethane at 0 - 84℃; for 15h; Lossen rearrangement; Inert atmosphere;	73%

: 942428-91-3
2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

: 149647-78-9
vorinostat

: 2,3,5-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20 - 20℃;	69%

: 942428-89-9
2,3,4,6-tetra-O-acetyl-D-galactosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

: 149647-78-9
vorinostat

: 931415-43-9
2,3,4,6-tetra-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-galactopyranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20 - 20℃;	69%

: 139486-67-2
mono-4-vinylbenzyl succinate

: 149647-78-9
vorinostat

: C27H32N2O6

Conditions

Conditions	Yield
Stage #1: mono-4-vinylbenzyl succinate With 1,1'-carbonyldiimidazole In dichloromethane for 0.166667h; Stage #2: vorinostat for 2h; Reagent/catalyst;	69%

: ethyl 7-(((S)-1-(((S)-1-((4-(bromomethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)amino)-7-oxoheptanoate

: 149647-78-9
vorinostat

: ethyl 7-(((S)-3-methyl-1-oxo-1-(((S)-1-oxo-1-((4-(((8-oxo-8-(phenylamino)octanamido)oxy)methyl)phenyl)amino)-5-ureidopentan-2-yl)amino)butan-2-yl)amino)-7-oxoheptanoate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	68%

: 366-18-7
[2,2]bipyridinyl

: copper(II) perchlorate hexahydrate

: 149647-78-9
vorinostat

: C24H27CuN4O3(1+)*ClO4(1-)

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 25℃; for 0.5h;	67.7%

...Expand

: copper(II) perchlorate hexahydrate

: 27318-90-7
1,10-phenanthroline-5,6-dione

: 149647-78-9
vorinostat

: Cu-SAHA-Phendio

Conditions

Conditions	Yield
With potassium hydroxide In methanol; ethanol; water at 25℃; for 0.5h;	67%

...Expand

: 6-(3-((4-(bromomethyl)phenyl)thio)-2,5-dioxopyrrolidin-1-yl)-N-(prop-2-yn-1-yl)hexanamide

: 149647-78-9
vorinostat

: N1-((4-((2,5-dioxo-1-(6-oxo-6-(prop-2-yn-1-ylamino)hexyl)pyrrolidin-3-yl)thio)benzyl)oxy)-N8-phenyloctanediamide

Conditions

Conditions	Yield
Stage #1: vorinostat With sodium hydroxide In methanol; water Stage #2: 6-(3-((4-(bromomethyl)phenyl)thio)-2,5-dioxopyrrolidin-1-yl)-N-(prop-2-yn-1-yl)hexanamide In methanol; water	67%
With sodium hydroxide In methanol Inert atmosphere;	40%

Vorinostat Chemical Properties

IUPAC Name: N'-Hydroxy-N-phenyloctanediamide
Synonyms of Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9): Vorinostat [USAN] ; CCRIS 8456 ; M344 ; N-Hydroxy-N'-phenyloctanediamide ; SAHA ; SAHA cpd ; Suberanilohydroxamic acid ; UNII-58IFB293JI ; Vorinostat ; Zolinza ; Suberoylanilide hydroxamic acid
CAS NO: 149647-78-9
Classification Code: Analgesics ; Analgesics, Non-Narcotic ; Anti-Inflammatory Agents ; Anti-Inflammatory Agents, Non-Steroidal ; Anticarcinogenic Agents ; Antineoplastic Agents ; Antirheumatic Agents ; Antitumor agent ; Enzyme Inhibitors ; Histone deacetylase inhibitor ; Peripheral Nervous System Agents ; Protective Agents ; Sensory System Agents
Molecular Formula of Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9): C₁₄H₂₀N₂O₃
Molecular Weight: 264.3202
Molecular Structure:

Melting Point: 161-162°C
Polar Surface Area: 49.85 Å²
Index of Refraction: 1.566
Molar Refractivity: 73.48 cm³
Molar Volume: 224.9 cm³
Surface Tension: 50.3 dyne/cm
Density of Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9): 1.174 g/cm³

Vorinostat Uses

Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9) is used as a powerful, selective, cell histone deacetylase inhibitors permeable (the HDAC). Display anti-angiogenic and vascular endothelial growth factor interference signal activity in human umbilical vein endothelial cells (endothelial cells).

Product Name

Vorinostat

Synthetic route

Vorinostat Chemical Properties

Vorinostat Uses

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