ChemicalBook CAS DataBase List Bortezomib

Bortezomib synthesis

5synthesis methods

Product Name:Bortezomib
CAS Number:179324-69-7
Molecular formula:C19H25BN4O4
Molecular Weight:384.24

Bortezomib is a dipeptide boronic acid analogue with antineoplastic activity. Bortezomib reversibly inhibits the 26S proteasome, a large protease complex that degrades ubiquinated proteins. By blocking the targeted proteolysis normally performed by the proteasome, bortezomib disrupts various cell signaling pathways, leading to cell cycle arrest, apoptosis, and inhibition of angiogenesis. Specifically, the agent inhibits nuclear factor (NF)-kappaB, a protein that is constitutively activated in some cancers, thereby interfering with NF-kappaB-mediated cell survival, tumor growth, and angiogenesis. In vivo, bortezomib delays tumor growth and enhances the cytotoxic effects of radiation and chemotherapy.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Peuchmaur, Marine; Lacour, Marie-Agnes; Sevalle, Jean; Lisowski, Vincent; Touati-Jallabe, Youness; Rodier, Fabien; Martinez, Jean; Checler, Frederic; Hernandez, Jean-Francois. Further characterization of a putative serine protease contributing to the γ-secretase cleavage of β-amyloid precursor protein. Bioorganic & Medicinal Chemistry. Institut des Biomolecules Max Mousseron, UMR5247 CNRS, Faculte de Pharmacie. Universites Montpellier 1 and 2. Montpellier, Fr. 34093. Volume 21. Issue 4. Pages 1018-1029. 2013

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7732-18-5
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179324-69-7
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Yield:179324-69-7 390 g

Reaction Conditions:

with hydrogenchloride;Dihydroxy-isobutyl-boran in methanol;hexane at 15 - 20; for 1 h;

Steps:

13

Dissolve the spin-dried b8 with methanol (4.75Kg), add it to the 30L reactor, then add n-hexane (3.95Kg) and isobutylboronic acid (0.3Kg), the temperature in the reactor was adjusted to 15-20 ° C, 1N hydrochloric acid (3Kg) was added dropwise, and the addition was completed in about 20-30 minutes. After 1 hour of reaction, the content of b8 was less than 1% by HPLC, and the reaction was terminated. Aspirate the reaction liquid into a 50L liquid separator to separate the n-hexane solution,Add an equal amount of n-hexane for extraction once. Then add pure water (12Kg) and dichloromethane (10Kg) to extract the product, separate the dichloromethane solution, add dichloromethane (5Kg) to extract, combine the extracts, and wash twice with water. Spin dry at 33 ° C, add ethyl acetate (5.52Kg) to dissolve, let stand at room temperature for 2 hours, place in freezer overnight, filter the next day, wash once with ethyl acetate, pump to dry, leave room for 2 hours, vacuum dry at 30 ° C After 10 hours, crude bortezomib (390g) was obtained, the yield in two steps was 67.66%, and the chromatographic purity 99.4%, melting point 169-173 ° C,

References:

CN104860975,2019,B Location in patent:Paragraph 0114; 0116

1029701-48-1
1 suppliers
inquiry

179324-69-7
693 suppliers
$16.00/5mg

References

205393-22-2
116 suppliers
inquiry

179324-69-7
693 suppliers
$16.00/5mg

References

13061-96-6
297 suppliers
$6.00/1g

1029701-48-1
1 suppliers
inquiry

179324-69-7
693 suppliers
$16.00/5mg

References

205393-22-2
116 suppliers
inquiry

13061-96-6
297 suppliers
$6.00/1g

179324-69-7
693 suppliers
$16.00/5mg

References

Bortezomib Related Search:

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