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Panobinostat
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Name

Panobinostat

 EINECS 803-814-1
CAS No. 404950-80-7 Density 1.241 g/cm3
PSA 77.15000 LogP 4.10900
Solubility N/A Melting Point 114-117?C
Formula C21H23N3O2 Boiling Point N/A
Molecular Weight 349.433 Flash Point N/A
Transport Information N/A Appearance Yellow solid
Safety 24/25 Risk Codes 22-36/37/38-20
Molecular Structure Molecular Structure of 404950-80-7 (Panobinostat) Hazard Symbols N/A
Synonyms

LBH589;N-Hydroxy-3-[4-[2-(2-methyl-1H-indol-3-yl)ethylaminomethyl]phenyl]-2(E)-propenamide;

Article Data 12

Panobinostat Synthetic route

441741-66-8

(E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride

404950-80-7

panobinostat

Conditions
ConditionsYield
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
441741-65-7

(E)-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylic acid methyl ester

404950-80-7

panobinostat

Conditions
ConditionsYield
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%

N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-L-tartarate

404950-80-7

panobinostat

Conditions
ConditionsYield
pH = 6.8 buffer;
960058-93-9

(E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid

404950-80-7

panobinostat

Conditions
ConditionsYield
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;

methyl (2E)-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoate hydrochloride

404950-80-7

panobinostat

Conditions
ConditionsYield
With hydroxylamine hydrochloride; potassium hydroxide In propan-1-ol; ethylene glycol at -6℃;77.0 g
2731-06-8

2-methyltryptamine

404950-80-7

panobinostat

Conditions
ConditionsYield
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
100-63-0

phenylhydrazine

404950-80-7

panobinostat

Conditions
ConditionsYield
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
5891-21-4

5-chloro-2-pentanone

404950-80-7

panobinostat

Conditions
ConditionsYield
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
404950-80-7

panobinostat

75-75-2

methanesulfonic acid

960055-60-1

N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide phosphate

Conditions
ConditionsYield
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;
404950-80-7

panobinostat

87-69-4

L-Tartaric acid

N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-L-tartarate

Conditions
ConditionsYield
In ethanol at 60℃; for 2h;96.6%
In ethanol at 60℃; Product distribution / selectivity;96.6%

Panobinostat Specification

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+

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