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CAS No.: | 404950-80-7 |
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Name: | Panobinostat |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C21H23N3O2 |
Molecular Weight: | 349.433 |
Synonyms: | LBH589;N-Hydroxy-3-[4-[2-(2-methyl-1H-indol-3-yl)ethylaminomethyl]phenyl]-2(E)-propenamide; |
EINECS: | 803-814-1 |
Density: | 1.241 g/cm3 |
Melting Point: | 114-117?C |
Appearance: | Yellow solid |
Risk Codes: | 22-36/37/38-20 |
Safety: | 24/25 |
PSA: | 77.15000 |
LogP: | 4.10900 |
(E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride
panobinostat
Conditions | Yield |
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Stage #1: (E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride With sodium hydroxide In methanol at -15 - -10℃; for 0.166667h; Stage #2: With hydroxylamine hydrochloride In methanol at -15 - -10℃; for 3.66667h; | 94.6% |
With hydroxylamine; potassium hydroxide In methanol at 0℃; for 4h; Inert atmosphere; | 73% |
With sodium hydroxide; hydroxylamine hydrochloride In water at 0℃; for 6h; | |
Stage #1: (E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride With hydroxylamine; sodium hydroxide In ethanol; water at 0℃; Stage #2: With hydrogenchloride In water |
(E)-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylic acid methyl ester
panobinostat
Conditions | Yield |
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With hyydroxylamine methanol; potassium hydroxide at 20℃; for 4h; Inert atmosphere; | 62.5% |
With hydroxylamine; potassium hydroxide In methanol at 20℃; for 6h; | 62.5% |
panobinostat
Conditions | Yield |
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pH = 6.8 buffer; |
(E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid
panobinostat
Conditions | Yield |
---|---|
Stage #1: (E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid With hydroxylamine In methanol; water at -15 - 25℃; Stage #2: With hydrogenchloride In water pH=10.3 - 10.7; |
panobinostat
Conditions | Yield |
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With hydroxylamine hydrochloride; potassium hydroxide In propan-1-ol; ethylene glycol at -6℃; | 77.0 g |
2-methyltryptamine
panobinostat
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 10 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere 3.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere 3.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme |
phenylhydrazine
panobinostat
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 10 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: ethanol / 4.5 h / 35 - 40 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 2.2: 6 h / 0 °C / Inert atmosphere 3.1: hydroxylamine; potassium hydroxide / methanol / 6 h / 20 °C View Scheme |
5-chloro-2-pentanone
panobinostat
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 10 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: ethanol / 4.5 h / 35 - 40 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 2.2: 6 h / 0 °C / Inert atmosphere 3.1: hydroxylamine; potassium hydroxide / methanol / 6 h / 20 °C View Scheme |
panobinostat
methanesulfonic acid
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide phosphate
Conditions | Yield |
---|---|
In ethyl acetate at 50℃; | 98.3% |
In ethyl acetate at 50℃; Product distribution / selectivity; | 98.3% |
In ethyl acetate at 20 - 50℃; Product distribution / selectivity; | |
In ethyl acetate at 4 - 20℃; Product distribution / selectivity; |
panobinostat
L-Tartaric acid
Conditions | Yield |
---|---|
In ethanol at 60℃; for 2h; | 96.6% |
In ethanol at 60℃; Product distribution / selectivity; | 96.6% |
The IUPAC name of Panobinostat is (E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide. With the CAS registry number 404950-80-7, it is also named as 2-Propenamide, N-hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)-, (2E)-. The product's category is Intracellular Signaling. It is yellow solid which is soluble in DMSO and methanol.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.58; (4)ACD/LogD (pH 7.4): 1.63; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 3.42; (7)ACD/KOC (pH 5.5): 2.04; (8)ACD/KOC (pH 7.4): 22.9; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.682; (13)Molar Refractivity: 106.66 cm3; (14)Molar Volume: 281.4 cm3; (15)Polarizability: 42.28×10-24 cm3; (16)Surface Tension: 58.2 dyne/cm; (17)Rotatable Bond Count: 7; (18)Tautomer Count: 3; (19)Exact Mass: 349.179027; (20)MonoIsotopic Mass: 349.179027; (21)Topological Polar Surface Area: 77.2; (22)Heavy Atom Count: 26; (23)Complexity: 474.
Uses of Panobinostat: It is an experimental drug developed by Novartis for the treatment of cancer. And it inhibits one or more of the histone deacetylase enzymes, a mechanism leading to apoptosis of malignant cells via multiple pathways.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(NO)\C=C\c1ccc(cc1)CNCCc3c2ccccc2nc3C
2. InChI:InChI=1/C21H23N3O2/c1-15-18(19-4-2-3-5-20(19)23-15)12-13-22-14-17-8-6-16(7-9-17)10-11-21(25)24-26/h2-11,22-23,26H,12-14H2,1H3,(H,24,25)/b11-10+