13174-73-7

Basic information

• Product Name: (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione
• Synonyms: (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione;(3S,6S)-3-(Hydroxymethyl)-6-methyl-2,5-piperazinedione;2,5-Piperazinedione, 3-(hydroxyMethyl)-6-Methyl-, (3S,6S)-
• CAS NO: 13174-73-7
• Molecular Formula: C6H10N2O3
• Molecular Weight: 158.16
• Mol File: 13174-73-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 560.6 °C at 760 mmHg
• Flash Point: 292.8 °C
• Appearance: /
• Density: 1.215
• CAS DataBase Reference: (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione(13174-73-7)
• EPA Substance Registry System: (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione(13174-73-7)

Safety Data

• Hazardous Substances Data: 13174-73-7(Hazardous Substances Data)

Usage

General Description

(3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione, also known as D-carnosine, is a naturally occurring dipeptide found in high concentrations in muscle and brain tissues. It is composed of the amino acids beta-alanine and histidine, and is known for its antioxidant and anti-aging properties. D-carnosine has been shown to protect cells from oxidative damage and reduce inflammation, making it a potential therapeutic agent for various age-related diseases and conditions. It also has potential applications in the food and cosmetic industries due to its ability to inhibit the formation of AGEs (advanced glycation end-products), which contribute to the aging process. Additionally, D-carnosine has been studied for its potential role in improving athletic performance and muscle function. Overall, (3S,6S)-3-(hydroxymethyl)-6-methylpiperazine-2,5-dione has diverse biological activities and holds promise for various applications in health and wellness.

Upstream product

• 1403898-61-2 (R)-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionyl-amino)propionic acid methyl ester 
• 195452-50-7 N-(2-bromo-propionyl)-serine 
• 3062-19-9 N-alanylserine 

Downstream Products

• 1403898-63-4 ((2R,5R)-5-methyl-piperazin-2-yl)-methanol hydrochloride 
• 2349395-78-2 1-tert-butyl 3-methyl (3R,6R)-6-methylpiperazine-1,3-dicarboxylate 
• 1604817-73-3 (2R,5S)-5-(2-cyanoimidazol-1-ylmethyl)-4-{2-[6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 1403903-28-5 (2R,5R)-5-chloromethyl-4-{2-[6-(4-fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 1403903-27-4 (2R,5R)-4-{2-[6-(4-fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 1403902-55-5 (2R,5R)-4-benzyl-5-chloromethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 1403901-32-5 (2R,5R)-4-benzyl-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 1403898-64-5 (2R,5R)-5-(hydroxymethyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Preparation method of chiral 1-tert-butyl-3-methyl-6-methylpiperazine-1, 3-diformate

The invention provides a preparation method of chiral 1-tert-butyl-3-methyl-6-methylpiperazine-1, 3-diformate, and particularly relates to a preparation method of (3R,6R) -1-tert-butyl-3-methyl-6-methylpiperazine-1, 3-diformate. The preparation method comprises the steps of taking Boc-D-alanine and L-serine methyl ester hydrochloride as initial raw materials, and preparing the chiral 1-tert-butyl-3-methyl-6-methylpiperazine-1, 3-diformate through condensation reaction, deamination protection, ring closing reaction, reduction reaction, amino protection, oxidation reaction, ring closing reactionand ring opening reaction. According to the preparation method provided by the invention, the Boc amino protective agent is used for protecting amino, so that the production cost is reduced, the rawmaterials are easy to obtain, the conditions are mild, the yield is relatively high, and the preparation method can be applied to large-scale industrial production.

Structure-based design and pharmacokinetic optimization of covalent allosteric inhibitors of the mutant gtpase krasg12c

Attempts to directly drug the important oncogene KRAS have met with limited success despite numerous efforts across industry and academia. The KRASG12C mutant represents an "Achilles heel" and has recently yielded to covalent targeting with small molecules that bind the mutant cysteine and create an allosteric pocket on GDP-bound RAS, locking it in an inactive state. A weak inhibitor at this site was optimized through conformational locking of a piperazine-quinazoline motif and linker modification. Subsequent introduction of a key methyl group to the piperazine resulted in enhancements in potency, permeability, clearance, and reactivity, leading to identification of a potent KRASG12C inhibitor with high selectivity and excellent cross-species pharmacokinetic parameters and in vivo efficacy.

CHEMICAL COMPOUNDS

The specification relates to compounds of Formula (I) and pharmaceutically acceptable salts thereof. The specification also relates to processes and intermediates used for their preparation, pharmaceutical compositions containing them and their use in the treatment of cell proliferative disorders.