434936-85-3

Basic information

• Product Name: Imidazo[1,2-a]pyrazin-8(7H)-one (9CI)
• Synonyms: Imidazo[1,2-a]pyrazin-8(7H)-one (9CI);Imidazo[1,2-a]pyrazin-8(7H)-one;8-Hydroxyimidazo[1,2-a]pyrazine;Imidazo[1,2-A]Pyrazin-8-Ol;Imidazo[1,2-a]pyrazin-8(7H);7H-Imidazo[1,2-a]pyrazin-8-one
• CAS NO: 434936-85-3
• Molecular Formula: C₆H₅N₃O
• Molecular Weight: 135.1234
• Product Categories: AMINETERTIARY
• Mol File: 434936-85-3.mol

Chemical Properties

• Appearance: /
• Density: 1.51 g/cm³
• Refractive Index: 1.738
• Storage Temp.: 2-8°C
• PKA: 10.23±0.20(Predicted)
• CAS DataBase Reference: Imidazo[1,2-a]pyrazin-8(7H)-one (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazo[1,2-a]pyrazin-8(7H)-one (9CI)(434936-85-3)
• EPA Substance Registry System: Imidazo[1,2-a]pyrazin-8(7H)-one (9CI)(434936-85-3)

Safety Data

• Hazardous Substances Data: 434936-85-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Imidazo[1,2-a]pyrazin-8(7H)-one (9CI) is utilized as a key building block in the synthesis of a variety of drugs and biologically active compounds. Its application is primarily due to its ability to participate in a broad spectrum of chemical reactions, which facilitates the development of new medications and other bioactive molecules.
Used in Medicinal Chemistry Research and Development:
In the field of medicinal chemistry, Imidazo[1,2-a]pyrazin-8(7H)-one (9CI) is employed as a valuable research target. Its unique structure and properties make it instrumental in the exploration of novel chemical pathways and the advancement of our understanding of molecular interactions within biological systems. Imidazo[1,2-a]pyrazin-8(7H)-one (9CI)'s potential in contributing to the discovery of innovative therapeutic agents is a significant aspect of its utility in this industry.

InChI:InChI=1/C6H5N3O/c10-6-5-7-1-3-9(5)4-2-8-6/h1-4H,(H,8,10)

Upstream product

• 434936-84-2 1-(2,2-diethoxyethyl)-1H-imidazole-2-carboxamide 

Downstream Products

• 434936-88-6 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one 
• 434936-89-7 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of 2-Nitroimidazopyrazin-one/-es with Antitubercular and Antiparasitic Activity

Tuberculosis and parasitic diseases, such as giardiasis, amebiasis, leishmaniasis, and trypanosomiasis, all urgently require improved treatment options. Recently, it has been shown that antitubercular bicyclic nitroimidazoles such as pretomanid and delamanid have potential as repurposed therapeutics for the treatment of visceral leishmaniasis. Here, we show that pretomanid also possesses potent activity against Giardia lamblia and Entamoeba histolytica, thus expanding the therapeutic potential of nitroimidazooxazines. Synthetic analogues with a novel nitroimidazopyrazin-one/-e bicyclic nitroimidazole chemotype were designed and synthesized, and structure-activity relationships were generated. Selected derivatives had potent antiparasitic and antitubercular activity while maintaining drug-like properties such as low cytotoxicity, good metabolic stability in liver microsomes and high apparent permeability across Caco-2 cells. The kinetic solubility of the new bicyclic derivatives varied and was found to be a key parameter for future optimization. Taken together, these results suggest that promising subclasses of bicyclic nitroimidazoles containing different core architectures have potential for further development.

Evaluation of novel third-strand bases for the recognition of a C·G base pair in the parallel DNA triple-helical binding motif

We describe the synthesis and the incorporation into oligonucleotides of the novel nucleoside building blocks 9, 10, and 16, carrying purine-like double H-bond-acceptor bases. These base-modified nucleosides were conceived to recognize selectively a cytosine · guanine (C·G) inversion site within a homopurine · homopyrimidine duplex, when constituent of a DNA third strand designed to bind in the parallel binding motif. While building block 16 turned out to be incompatible with standard oligonucleotide-synthesis conditions, UV/triplex melting experiments with third-strand 15-mers containing β-D-nucleoside 6 (from 9) showed that recognition of the four natural Watson-Crick base pairs follows the order G·C ? C·G > A· T> T·A. The recognition is sequence-context sensitive, and G·C or C·G recognition does not involve protonated species of β-D-nucleoside 6. The data obtained fit (but do not prove) a structural model for C · G recognition via one conventional and one C - H··· O H-bond. The unexpected G · C recognition is best explained by third-strand base intercalation. A comparison of the triplex binding properties of these new bases with those of 4-deoxothymine (5-methylpyrimidine-2(1H)-one, 4HT), previously shown to be C·G selective but energetically weak, is also described.