90802-45-2

Basic information

• Product Name: 2,6-Piperidinedione, 3-amino-, monohydrobromide
• CAS NO: 90802-45-2
• Molecular Formula: C5H8N2O2.BrH
• Molecular Weight: 209.043
• Mol File: 90802-45-2.mol

Chemical Properties

• CAS DataBase Reference: 2,6-Piperidinedione, 3-amino-, monohydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Piperidinedione, 3-amino-, monohydrobromide(90802-45-2)
• EPA Substance Registry System: 2,6-Piperidinedione, 3-amino-, monohydrobromide(90802-45-2)

Safety Data

• Hazardous Substances Data: 90802-45-2(Hazardous Substances Data)

Usage

General Description

2,6-Piperidinedione, 3-amino-, monohydrobromide is a chemical compound that is a derivative of piperidinedione, a heterocyclic organic compound. 2,6-Piperidinedione, 3-amino-, monohydrobromide is a monohydrobromide salt, indicating that it has one molecule of hydrobromic acid bound to the piperidinedione. The 3-amino group in the compound suggests the presence of an amine functional group, which can contribute to its reactivity and potential biological activity. This chemical may have applications in organic synthesis, pharmaceuticals, and other industrial processes. It is important to handle and use 2,6-Piperidinedione, 3-amino-, monohydrobromide with care, following proper safety protocols and guidelines.

Upstream product

• 24666-55-5 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine 
• 2650-64-8 Cbz-L-Gln 
• 85535-45-1 5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid 
• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 

Downstream Products

• 827026-45-9 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 6139-18-0 N-(o-Carboxybenzoyl)-D,L-glutamic acid imide 
• 94464-26-3 4-(benzyloxy)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 94464-27-4 2-(2,6-dioxo-3-piperidinyl)-5-benzyloxy-1H-isoindole-1,3(2H)-dione 
• 537696-00-7 2-amino-N-(2,6-dioxo-piperidin-3-yl)benzamide 

Relevant articles and documents

Preparation method of lenadomide

The invention discloses a preparation method of lenalidomide, and belongs to the field of organic synthesis. 2-methyl-3-methyl nitrobenzoate and 3-N-benzyloxy-carbonyl-L-glutamine serve as starting materials, and an important intermediate 2-brooethyl-3-methyl nitrobenzoate is obtained through a bromination reaction of 2-methyl-3-methyl nitrobenzoate. 3-N-benzyloxy-carbonyl-L-glutamine is cyclizedunder catalysis to produce 3-N-benzyloxy-carbonyl-2,6-dioxopiperidine, an amino group is subjected to deprotection to produce 3-amino-2,6-piperidone halide, 3-(4-nitro-1-oxo-1,3-o-xylylenimine-2-yl)piperidine-2,6-diketone is obtained through an aminolysis reaction of 3-N-benzyloxy-carbonyl-2,6-dioxopiperidine and 2-brooethyl-3-methyl nitrobenzoate, and then lenalidomide is prepared through reduction. The method has the advantages that the cost of raw materials are low, aftertreatment is simple, and the yield is high, and the production cost of the lenalidomide as a bulk drug is greatly reduced. The method is a convenient and efficient lenalidomide synthesis method suitable for industrial production.

Hydrolyzed metabolites of thalidomide: Synthesis and TNF-α production-inhibitory activity

Putative hydrolyzed metabolites of thalidomide were prepared and characterized, and their inhibitory activity on tumor necrosis factor (TNF)-α production in the human monocytic leukemia cell line THP-1 was evaluated. α-(2-Carboxybenzamido)glutarimide was a more potent TNF-α production inhibitor than thalidomide.

Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity

A thalidomide-binding aptamer was produced by systematic evolution of ligands by exponential enrichment from a library of non-natural DNA in which thymidine had been replaced with a modified deoxyuridine bearing a cationic functional group via a hydrophobic methylene linker at the C5 position. The additional functional group in the modified DNA aptamer could improve stability against nucleases and increase the binding affinity to thalidomide. The selected aptamer could recognize thalidomide enantioselectively, although a racemic thalidomide-attached gel was used for the selection. Surface plasmon resonance and fluorescence titration studies revealed that the selected modified DNA aptamer and a truncated version bound with an (R)-thalidomide derivative with high enantioselectivity, but not with the (S)-form. The modified group in the DNA aptamer is indispensable for the interaction with thalidomide, as the corresponding natural type DNA bearing the same base sequence showed no binding affinity with (R)-nor (S)-thalidomide. Computational sequence analysis suggested that the selected apatamer (108mer) could fold into a three-way junction structure; however, truncation of this aptamer (31 mer) revealed that the thalidomide-binding site is a hairpin-bulge region that is a component of one of the arms of the three-way junction structure. The Kd value of the truncated 31 mer aptamer for binding with the (R)-thalidomide derivative was 1.0 μM estimated from fluorescence titration study. The aptamer that can recognize a single enantiomer of thalidomide will be useful as a biochemical tool for the analysis and study of the biological action of thalidomide enantiomers.

Mono- and dihydroxylated metabolites of thalidomide: Synthesis and TNF-α production-inhibitory activity

Mono- and dihydroxylated metabolites of thalidomide were efficiently prepared and characterized, and their inhibitory activity on tumor necrosis factor (TNF)-α production in the human monocytic leukemia cell line THP-1 was evaluated. 5,N-Dihydroxythalidomide was a much more potent TNF-α production inhibitor than thalidomide.

Studies towards the synthesis of the benzodiazepine alkaloid auranthine. Synthesis of an acetylated derivative

Different approaches towards the synthesis of auranthine have been investigated. A completed synthesis of 3-[2-(4-oxo-3,4-dihydro-quinazolin-2-yl)- ethyl]-3,4-dihydro-1H-benzo[e][1,4]-diazepine-2,5-dione, an auranthine precursor, which after dehydration w

Studies on Synthesis and Anticancer Activity of Selected N-(2-Fluoroethyl)-N-nitrosoureas

An activated carbamate, 2-nitrophenyl (2-fluoroethyl)nitrosocarbamate (3), was used to advantage in the synthesis of the water-soluble (2-fluoroethyl)nitrosoureas 6a-d from 2-aminoethanol, (1α,2β,3α)-2-amino-1,3-cyclohexanediol, cis-2-hydroxycyclohexanol, and 2-amino-2-deoxy-D-glucose.In a variation of this method, 2,4,5-trichlorophenyl (2-fluoroethyl)carbamate (4) was used to prepare the urea from which the essentially water-insoluble N'-(2,6-dioxo-3-piperidinyl)-N-(2-fluoroethyl)-N-nitrosourea (6e) was derived.The anticancer activity of these nitrosoureas was determined against the murine tumors B16 melanoma and Lewis lung carcinoma and found to be significant and comparable to their chloroethyl counterparts.On the basis of results from both systems, the dihydroxycyclohexyl derivative 6b may be the most effective.