64951-10-6

Usage

Uses

Used in Pharmaceutical Industry:
IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID is used as a key building block for the synthesis of biologically active molecules, specifically in the development of pharmaceutical drugs. Its unique structure allows for the creation of new drug candidates with potential therapeutic applications.
Used in Pesticide Industry:
IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID is used as a pesticide intermediate, contributing to the development of new pesticides with improved efficacy and selectivity in controlling pests and diseases in agriculture.
Used in Organic Synthesis:
IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID is utilized as a versatile compound in organic synthesis, enabling the design and synthesis of a wide range of chemical compounds with diverse applications in various industries.

InChI:InChI=1/C7H5N3O2/c11-6(12)5-4-10-3-1-2-8-7(10)9-5/h1-4H,(H,11,12)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 1113-59-3 bromopyruvic acid 

Relevant academic research and scientific papers

Structural modification of zolpidem led to potent antimicrobial activity in imidazo[1,2-: A] pyridine/pyrimidine-1,2,3-triazoles

Ambien (zolpidem), an imidazo[1,2-a]pyridine derivative, is a commercial drug to treat insomnia which also possesses antitubercular activity against Mycobacterium tuberculosis H37Rv. In this paper, we describe the synthesis of three diverse lead series of imidazo[1,2-a]pyridine/pyrimidine-1,2,3-triazoles (IPTs) which are designed by specific structural modifications of zolpidem. Most of the IPTs exhibited remarkable in vitro antitubercular activity with an MIC of 1.56 μg mL-1, which is two-fold higher than the MIC of zolpidem. Further, the synthesized IPTs displayed moderate inhibitory activity against several bacterial and fungal strains as well, and also showed an acceptable safety profile as verified through in vitro cytotoxicity assessment against Vero cells. In addition, the potent IPTs exhibited promising binding interactions within the active site of the InhA enzyme. An interesting correlation between the in vitro inhibitory activity and the binding mode was observed: most of the potent molecules (MIC = 1.56 μg mL-1) interact through a H-bond with the Tyr 158 residue of the target enzyme. These efforts toward the structural modification of zolpidem could be helpful for further optimization of the IPT core to develop new anti-TB drugs.

Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles

[Chemical equation presented] The first continuous flow synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids directly from 2-aminopyridines and bromopyruvic acid has been developed, representing a significant advance over the corresponding in-flask method. The process was applied to the multistep synthesis of imidazo[1,2-a]pyridine-2-carboxamides, including a Mur ligase inhibitor, using a two microreactor, multistep continuous flow process without isolation of intermediates.