52065-78-8

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Piperidinedione is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form complex structures with biological targets makes it a valuable building block for the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, 2,5-Piperidinedione is used as a versatile intermediate for the preparation of a wide range of compounds, including piperidine-dione derivatives. The synthesis process involves several steps, such as lactonization, reduction, azidation, reductive ring expansion, and Dess-Martin Periodinane oxidation, which allow for the creation of diverse chemical entities with potential applications in various fields.
Used in Research and Development:
2,5-Piperidinedione is also employed in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique structure and reactivity make it an attractive candidate for the development of new synthetic methodologies and the creation of innovative molecular architectures.

InChI:InChI=1/C5H7NO2/c7-4-1-2-5(8)6-3-4/h1-3H2,(H,6,8)

Upstream product

• 5154-01-8 2,5-dihydroxypyridine 
• 90292-53-8 5-benzyloxy-N-benzylpyridine-2-one 
• 106-60-5 ALA 
• 85-61-0 coenzyme A 
• 79416-27-6 methyl aminolevulinate 
• 617-65-2 Glutamic acid 
• 4344-84-7 5-oxo-tetrahydro-furan-2-carboxylic acid 
• 10374-51-3 5-hydroxymethyl-4,5-dihydrofuranone 
• 19365-07-2 (RS)-5-hydroxypiperidin-2-one 
• 142-08-5 2-Pyridone 

Downstream Products

• 19365-07-2 (RS)-5-hydroxypiperidin-2-one 
• 5451-09-2 5-aminolevulinic acid hydrochloride 
• 87179-79-1 1-benzyl-5-(benzyloxy)piperidin-2-one 
• 87179-80-4 1-benzyl-5-hydroxypiperidin-2-one 

Relevant academic research and scientific papers

Preparation method of 2,5-piperidione

The invention relates to a preparation method of 2,5-piperidione. 2-glutamic acid is used as a starting raw material to perform closed loop reaction to produce a compound 2 under the effects of NaNO2; a compound 3 is produced through borane reduction; a compound 4 is produced under the effects of methylsufonyl chloride; a compound 5 is produced through substitution under the sodium azide effect; a compound 6 is produced through Pd/H2 under the reduction effect; a target compound is generated under the effect of Dess-Martin periodinane. The preparation method has the advantages that the raw materials are cheap and can be easily obtained; the synthetic method is simple; the method belongs to a fire-new method for synthesizing 2,5-piperidione. The method meets the requirements of large-scale industrial production.

Preparation method of pipyridine-2,5-dione and Pharmaceutical composition comprising the same

The present invention relates to a novel method for preparing pipyridine-2,5-dione and use of pipyridine-2,5-dione for alleviating or treating skin diseases in the form of a pharmaceutical composition or a cosmetic composition. According to the present invention, pipyridione-2,5-dione has higher stability than any other ALA derivatives and causes no change in functions of ALA, and thus can be useful for treating skin diseases or the like. In addition, the composition according to the present invention shows a better therapeutic effect, when it is applied locally to a skin disease site. Thus, the composition can be useful for developing an agent for treating hardly curable diseases, such as psoriasis.COPYRIGHT KIPO 2016

A three enzyme pathway for 2-amino-3-hydroxycyclopent-2-enone formation and incorporation in natural product biosynthesis

A number of natural products contain a 2-amino-3-hydroxycyclopent-2-enone five membered ring, termed C5N, which is condensed via an amide linkage to a variety of polyketide-derived polyenoic acid scaffolds. Bacterial genome mining indicates three tandem ORFs that may be involved in C5N formation and subsequent installation in amide linkages. We show that the protein products of three tandem ORFs (ORF33-35) from the ECO-02301 biosynthetic gene cluster in Streptomyces aizunenesis NRRL-B-11277, when purified from Escherichia coli, demonstrate the requisite enzyme activities for C5N formation and amide ligation. First, succinyl-CoA and glycine are condensed to generate 5-aminolevulinate (ALA) by a dedicated PLP-dependent ALA synthase (ORF34). Then ALA is converted to ALA-CoA through an ALA-AMP intermediate by an acyl-CoA ligase (ORF35). ALA-CoA is unstable and has a half-life of ～10 min under incubation conditions for off-pathway cyclization to 2,5-piperidinedione. The ALA synthase can compete with the nonenzymatic decomposition route and act in a novel second transformation, cyclizing ALA-CoA to C5N. C 5N is then a substrate for the third enzyme, an ATP-dependent amide synthetase (ORF33). Using octatrienoic acid as a mimic of the C56 polyenoic acid scaffold of ECO-02301, formation of the octatrienyl-C 5N product was observed. This three enzyme pathway is likely the general route to the C5N ring system in other natural products, including the antibiotic moenomycin.

A Three-Step Synthesis of δ-Aminolaevulinic Acid

Piperidine-2,5-dione (4) is prepared by catalytic hydrogenation of 5-hydroxy-2-pyridone (3).Ring opening of the lactam 4 with concentrated hydrochloric acid yields the hydrochloride of δ-aminolaevulinic acid (2).