324737-10-2

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-Methyl-3-oxo-3-(pyrazin-2-yl)propanoate is used as a building block for the synthesis of various drugs and chemicals. Its unique structure and potential biological activity make it a key component in the development of new pharmaceuticals.
Used in Chemical Research:
In the field of chemical research, Methyl 2-Methyl-3-oxo-3-(pyrazin-2-yl)propanoate serves as an important intermediate for creating a variety of chemical compounds. Its versatility allows researchers to explore its potential in different chemical reactions and syntheses.

Upstream product

• 554-12-1 propanoic acid methyl ester 
• 6924-68-1 ethyl 2-pyrazinecarboxylate 
• 98-97-5 2-pyrazylcarboxylic acid 
• 6164-79-0 methyl pyrazine-2-carboxylate 

Downstream Products

• 64224-21-1 Oltipraz 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor

Hypoxia-inducible factor-1 (HIF-1) is a key transcription factor which is strongly associated with tumor survival, progression, and therapeutic resistance. Accordingly, it has been suggested that the inhibition of the HIF-1 pathway can suppress tumor, and it has become an important therapeutic target. In present study, oltipraz, its metabolite M2, and their derivatives were synthesized and evaluated as HIF-1α inhibitors. Among the synthesized, benzyl-substituted pyrrolo[1,2-a]pyrazine 2g most potently inhibited HIF-1α protein accumulation (81% at 10 μM) and VEGF, GLUT-1 transcription (77% and 92% at 10 μM, respectively).

METHODS FOR PREPARING OLTIPRAZ

The invention provides improved methods of synthesizing oltipraz, which result in higher overall yield and better purity of the desired product.

METHOD FOR PREPARING OLTIPRAZ

Provided is a method for preparing oltipraz. The method includes reacting methyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate with phosphorus pentasulfide in the presence of a mixed solvent of toluene and xylene, followed by recrystallization.

Dithiolthione compounds for the treatment of neurological disorders and for memory enhancement

The invention provides methods to treat neurological disorders such as Alzheimer's disease, or to slow the progression of such diseases, or to treat and/or prevent other disorders as disclosed in the specification, by administering to patients, or delivering to the tissues of such patients, oltipraz or related compounds as disclosed in the specification.

Structural determinants for AMPA agonist activity of aryl or heteroaryl substituted AMPA analogues. Synthesis and pharmacology

We have previously reported the synthesis and pharmacological characterization of analogues of 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA, 1a), in which the methyl group was replaced by a phenyl group (APPA, 1b) or heteroaryl groups. While 2b and its 3-pyridyl analogue 2-amino-3-[3-hydroxy-5-(3-pyridyl)-4-isoxazolyl]propionic acid (3-Py-AMPA, 3) show very low affinity for AMPA receptors, introduction of heteroaryl substituents containing heteroatom in the 2-position provides potent AMPA receptor agonists. We here report the synthesis and pharmacology of 2-amino-3-(3-hydroxy-5-pyrazinyl-4-isoxazolyl)propionic acid (7) (IC50 = 1.2 μM; EC50 = 11 μM), which is weaker as an AMPA agonist than AMPA (IC50 = 0.040 μM; EC50 = 3.5 μM) but comparable in potency with 2-Py-AMPA (4) (IC50 = 0.57 μM; EC50 = 7.4 μM), as determined in radioligand binding and electrophysiological experiments, respectively. The AMPA analogues 8a-c, containing 2-, 3-, or 4-methoxyphenyl substituents, respectively, and the corresponding hydroxyphenyl analogues, 9a-c, were also synthesized and evaluated pharmacologically. With the exception of 2-amino-3-[3-hydroxy-5-(2-hydroxyphenyl)-4-isoxazolyl]propionic acid (9a), which is a very weak AMPA agonist (IC50 = 45 μM; EC50 = 324 μM), none of these compounds showed detectable effect at AMPA receptors.