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| CAS No.: | 179324-69-7 |
|---|---|
| Name: | Bortezomib |
| Molecular Structure: | |
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| Formula: | C19H25BN4O4 |
| Molecular Weight: | 384.243 |
| Synonyms: | Pyz-Phe-boroLeu;Boronic acid, [(1(R)-3-methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]-;Boronic acid, [1-[[1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl) amino]propyl]amino]-3-methylbutyl]-, L-(S)-;[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl]amino]butyl]boronic acid;PS 341 (pharmaceutical); |
| EINECS: | 605-854-3 |
| Density: | 1.214 g/cm3 |
| Melting Point: | 122-124 °C |
| Appearance: | yellow solid |
| Risk Codes: | 23/24/25-48/23/24/25 |
| Safety: | 9-27-36/37-45-60 |
| PSA: | 124.44000 |
| LogP: | 1.56230 |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; acetone at 20℃; | 94% |
N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide
dihydroxy-methyl-borane
velcade
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; acetone at 20℃; for 40h; | 92% |
velcade
| Conditions | Yield |
|---|---|
| With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale; | 86% |
velcade
| Conditions | Yield |
|---|---|
| With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale; | 86% |
velcade
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol; water at 20℃; | 82.3% |
velcade
| Conditions | Yield |
|---|---|
| With hydrogenchloride; 2-methyl-propan-1-ol In methanol; pentane at 0 - 20℃; for 12h; Large scale; | 82% |
N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide
velcade
| Conditions | Yield |
|---|---|
| With hydrogenchloride; Dihydroxy-isobutyl-boran In water at 20℃; Solvent; Temperature; | 77% |
| With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; n-heptane; water at 25 - 30℃; for 1 - 2h; Product distribution / selectivity; | 70% |
| With hydrogenchloride; Dihydroxy-isobutyl-boran; water In methanol; hexane at 20℃; for 18h; | 56.4% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol; n-heptane; water at 0 - 25℃; for 2h; | 71.5% |
| Conditions | Yield |
|---|---|
| Stage #1: N-benzyl-L-phenylalanine; (R)-1-amino-3-methylbutylboronic acid pinanediol ester hydrochloride With 4-methyl-morpholine; N-ethyl-N,N-diisopropylamine; isobutyryl chloride In tetrahydrofuran at 55℃; for 2h; pH=10; Inert atmosphere; Stage #2: With palladium on activated charcoal; hydrogen In tetrahydrofuran at 68℃; under 4560.31 Torr; for 2h; Stage #3: 2-pyrazylcarboxylic acid Concentration; Temperature; Solvent; pH-value; Pressure; Further stages; | 67% |
| Conditions | Yield |
|---|---|
| Stage #1: C23H27BNO5Pol With piperidine In N,N-dimethyl-formamide for 0.333333h; 1-glycerol polystyrene resin; Stage #2: N-Fmoc L-Phe With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 2h; 1-glycerol polystyrene resin; Stage #3: 2-pyrazylcarboxylic acid Further stages; | 54% |
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IUPAC Name: [(1R)-3-Methyl-1-[[(2S)-3-phenyl-2-(pyrazine-2-carbonylamino)propanoyl] amino]butyl]boronic acid
Molecular Formula: C19H25BN4O4
Molecular Weight: 384.24 g/mol
SMILES: O=C(N[C@@H](C(=O)N[C@@H](B(O)O)CC(C)C)Cc1ccccc1)c2nccnc2 Copy
InChI: InChI=1/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m1/s1
Product Categories: Boron Derivatives; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
Classification Code: Antineoplastic Agents; Enzyme Inhibitors; Protease Inhibitors; Treatment of multiple cancers, including multiple myeloma, chronic lymphocytic leukemia, non-Hodgkins lymphoma, and pancreatic, colon, lung, and prostate cancers [proteasome inhibitor]
Melting Point: 122-124 °C
Index of Refraction: 1.564
Molar Refractivity: 102.97 cm3
Molar Volume: 316.5 cm3
Surface Tension: 53.2 dyne/cm
Density of Bortezomib (CAS NO.179324-69-7): 1.214 g/cm3
In 1995, Bortezomib was first synthesized at a company called Myogenics, which soon changed its name to ProScript.
Bortezomib is the first proteasome inhibitor to be approved b the US FDA for multiple myeloma, a blood cancer. A reversible inhibitor of the 26S proteasome-a barrel-shaped multiprotein particle found in the nucleus and cytosol of all eukaryotic cel.It is approved in the U.S. for treating relapsed multiple myeloma and mantle cell lymphoma.
It is used as a medicine to treat some refractory disease, for example relapsed multiple myeloma and mantle cell lymphoma.
Bortezomib (CAS NO.179324-69-7), its Synonyms are ((1R)-3-Methyl-1-(((2S)-3-phenyl-2-((pyrazinylcarbonyl)amino)propanoyl)amino)butyl)boronic acid ; Boronic acid, ((1R)-3-methyl-1-(((2S)-1-oxo-3-phenyl-2-((pyrazinylcarbonyl)amino)propyl)amino)butyl)- ; N-((1S)-1-Benzyl-2-(((1R)-1-(dihydroxyboranyl)-3-methylbutyl)amino)-2-oxoethyl)pyrazinecarboxamide ; Velcade . It is yellow solid.
