Products Categories
CAS No.: | 149647-78-9 |
---|---|
Name: | Vorinostat |
Article Data: | 39 |
Molecular Structure: | |
Formula: | C14H20N2O3 |
Molecular Weight: | 264.324 |
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; |
EINECS: | 682-505-1 |
Density: | 1.174 g/cm3 |
Melting Point: | 161-162 °C |
Appearance: | white crystalline solid |
Hazard Symbols: | T |
Risk Codes: | 61-68 |
Safety: | 53-36/37-45 |
PSA: | 78.43000 |
LogP: | 2.93500 |
7-phenylcarbamoyl heptanoic acid methyl ester
vorinostat
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% |
vorinostat
Conditions | Yield |
---|---|
With 10 wt% Pd(OH)2 on carbon; hydrogen; trifluoroacetic acid In methanol at 20℃; for 2h; | 91% |
N-phenylhexanamide
vorinostat
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In N,N-dimethyl-formamide at 40℃; for 1h; Reagent/catalyst; | 88.5% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide; potassium hydroxide In ethanol at 50℃; for 0.5h; | 82.4% |
With dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole In tetrahydrofuran |
suberanilic acid
vorinostat
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% |
7-phenylcarbamoyl heptanoic acid methyl ester
A
suberanilic acid
B
vorinostat
Conditions | Yield |
---|---|
With water; hydroxylamine; sodium methylate In methanol at 90℃; | A 15% B 80% |
vorinostat
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 |
suberic acid monomethyl ester
vorinostat
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 |
aniline
vorinostat
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 |
octane-1,8-dioic acid
vorinostat
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 |
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
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).