7144-20-9

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4,6-DIMETHYL-3-PYRIDINECARBOXAMIDE is used as a chemical intermediate for the preparation of 2,6,8-trisubstituted 1-deazapurines. These deazapurines serve as adenosine receptor antagonists, which have potential applications in the development of drugs targeting adenosine receptors. Adenosine receptor antagonists are of interest due to their potential therapeutic effects in various conditions, including asthma, chronic obstructive pulmonary disease (COPD), and neurodegenerative disorders.

InChI:InChI=1/C8H11N3O/c1-4-3-5(2)11-7(9)6(4)8(10)12/h3H,1-2H3,(H2,9,11)(H2,10,12)/p+1

Upstream product

• 123-54-6 acetylacetone 
• 34570-17-7 malonamamidine hydrochloride 
• 28491-67-0 4,6-dimethyl-3-oxo-2,3-dihydro-1H-pyrazolo<3,4-b>pyridine 

Downstream Products

• 1146967-25-0 C₁₇H₁₉N₃O₃ 
• 1146967-26-1 C₁₅H₁₃Cl₂N₃O 
• 1146967-22-7 C₁₇H₁₉N₃O₃ 
• 1146967-29-4 C₁₆H₁₇N₃O₃ 
• 1146967-32-9 C₁₅H₁₅N₃O₂ 
• 1146967-23-8 C₁₆H₁₇N₃O₂ 
• 1146967-24-9 C₁₈H₂₁N₃O₄ 
• 1146967-27-2 C₁₇H₁₉N₃O 
• 1146967-30-7 C₁₇H₁₉N₃O₂ 
• 1146967-28-3 C₁₇H₁₇N₃O₃ 
• 1146967-31-8 C₁₆H₁₇N₃O₃ 
• 2078-87-7 5,7-dimethyl-2-phenyl-2,3-dihydro-1H-pyrido[2,3-d][1,3,2]diazaborinin-4-one 
• 24667-09-2 2-hydroxy-4,6-dimethylnicotinic acid 

Relevant academic research and scientific papers

Design and synthesis of potent and orally active GPR4 antagonists with modulatory effects on nociception, inflammation, and angiogenesis

GPR4, a G-protein coupled receptor, functions as a proton sensor being activated by extracellular acidic pH and has been implicated in playing a key role in acidosis associated with a variety of inflammatory conditions. An orally active GPR4 antagonist 39c was developed, starting from a high throughput screening hit 1. The compound shows potent cellular activity and is efficacious in animal models of angiogenesis, inflammation and pain.

Discovery of a series of imidazo[4,5-b ]pyridines with dual activity at angiotensin II Type 1 receptor and peroxisome proliferator-activated receptor-γ

Mining of an in-house collection of angiotensin II type 1 receptor antagonists to identify compounds with activity at the peroxisome proliferator-activated receptor-γ (PPARγ) revealed a new series of imidazo[4,5-b]pyridines 2 possessing activity at these

Synthesis of new 2-substituted pyrido[2,3-d]pyrimidin-4(1H)-ones and their antibacterial activity

2-Substituted-5,7-dimethyl pyrido[2,3-d]pyrimidin-4(1H)-ones (8) were synthesized by oxidation of 2-substituted-5,7-dimethyl dihydropyrido[2,3-d]pyrimidin-4(1H)-ones (7) which were in turn prepared from 2-amino-4,6-dimethyl nicotinamide (5) and substituted aryl aldehydes (6). 2-Amino-4,6-dimethyl nicotinamide (5) was prepared from ethyl cyanoacetate (1) via malonamamidine hydrochloride (3). The compounds were characterized by IR, NMR, MS and elemental analyses. Compounds 7 and 8 were screened for antibacterial activity against Gram positive and Gram negative bacteria. Dehydrogenated compounds (8) showed less antibacterial activity than the compounds 7. Among all the test compounds screened for antibacterial activity 7c (1.25 μg/ml) showed greater activity. All the synthesized compounds were found inactive when screened for antifungal activity at the concentration of 200 μg/ml.

2,6,8-Trisubstituted 1-deazapurines as adenosine receptor antagonists

In this study we developed a refined pharmacophore model for antagonists of the human adenosine A1 receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A1 receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying Ki values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A1 receptor with > 300-fold and 45-fold selectivity toward A2A and A3 receptors, respectively. Compound 14 (LUF 5981, Ki = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A2A (> 200-fold) and A 3 (700-fold) receptors.

New approach to the imidazolutidine moiety of MK-996

A highly effective, regio-selective synthesis of imidazolutidine (1) is described starting from readily available malonamamidine hydrochloride and 2,4-pentanedione.