26228-95-5

Basic information

• Product Name: 3,3-dibromo-2-piperidone
• Synonyms: 3,3-Dibromo-2-piperidinone;3,3-dibromo-2-piperidone;3,3-dibromopiperidin-2-one
• CAS NO: 26228-95-5
• Molecular Formula: C₅H₇Br₂NO
• Molecular Weight: 256.94
• Mol File: 26228-95-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 170-171 °C
• Boiling Point: 330.6±42.0 °C(Predicted)
• Appearance: /
• Density: 2.036±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.26±0.40(Predicted)
• CAS DataBase Reference: 3,3-dibromo-2-piperidone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-dibromo-2-piperidone(26228-95-5)
• EPA Substance Registry System: 3,3-dibromo-2-piperidone(26228-95-5)

Safety Data

• Hazardous Substances Data: 26228-95-5(Hazardous Substances Data)

Upstream product

• 675-20-7 piperidin-2-one 
• 756874-11-0 5-methoxycarbonylamino-valeric acid 
• 660-88-8 5-aminopentanoic acid 
• 34433-86-8 3-bromo-2-piperidinone 

Downstream Products

• 34433-86-8 3-bromo-2-piperidinone 
• 1571062-21-9 (E)-3-bromo-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one 
• 1571062-22-0 (E)-3-bromo-1-(2-methyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one 
• 1571062-23-1 (E)-3-bromo-1-(2-ethyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one 
• 1571062-24-2 (E)-3-bromo-1-(2-propyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one 
• 1571062-25-3 (E)-3-bromo-1-(2-butyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one 
• 614754-01-7 2-oxopiperidin-3-yl acetate 

Relevant articles and documents

DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF

The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to a pharmaceutical composition and formulation containing a derivative of piperlongumine; and use of the derivatives and analogs for treating cancer, reducing inflammation and/or treating an autoimmune or inflammatory disease.

DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF

The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3- dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to processes for preparing the same; a pharmaceutical composition and formulation containing a derivative of piperlogumine; and use of the derivatives and analogs for treating cancer.

Novel Ligustrazine-Based Analogs of Piperlongumine Potently Suppress Proliferation and Metastasis of Colorectal Cancer Cells in Vitro and in Vivo

Piperlongumine 1 increases reactive oxygen species (ROS) levels and preferably induces cancer cell apoptosis by triggering different pathways. However, the poor solubility of 1 limits its intensive investigation and clinical application. Ligustrazine possesses a water-soluble pyrazine skeleton and can inhibit proliferation and metastasis of cancer cells. We synthesized compound 3 by replacement of the trimethoxyphenyl of 1 with ligustrazine moiety and further introduced 2-Cl, -Br, and -I to 3 for synthesis of 4-6, respectively. Compound 4 possessed 14-fold greater aqueous solubility than 1 and increased ROS levels in colorectal cancer HCT-116 cells. Additionally, 4 preferably inhibited proliferation, migration, invasion, and heteroadhesion of HCT-116 cells. Treatment with 4 suppressed tumor growth and lung metastasis in vivo and prolonged the survival of tumor-bearing mice. Furthermore, 4 mitigated TGF-β1-induced epithelial-mesenchymal transition and Wnt/β-catenin activation by inhibiting the Akt and GSK-3β phosphorylation in HCT-116 cells. Collectively, 4 displayed significant antiproliferation and antimetastasis activities, superior to 1.