251-80-9

Usage

Uses

Used in Pharmaceutical Industry:
1H-Imidazo(1,2-b)pyrazole is used as a pharmaceutical agent for its anti-inflammatory, antiviral, and anticancer properties, offering potential therapeutic benefits in the treatment of various diseases and conditions.
Used in Agrochemical Industry:
1H-Imidazo(1,2-b)pyrazole is utilized as an agrochemical compound, leveraging its biological activities to contribute to the development of effective pest control and crop protection solutions.
Used in Synthesis of Biologically Active Compounds:
1H-Imidazo(1,2-b)pyrazole is used as a key intermediate in the synthesis of various biologically active compounds, facilitating the creation of new drugs and therapeutic agents with potential applications in medicine.
Used in Ligand Synthesis for Metal-Catalyzed Reactions:
1H-Imidazo(1,2-b)pyrazole is employed as a ligand in the synthesis of metal-catalyzed reactions, enabling the development of novel chemical processes and catalytic systems in the field of organic chemistry.

InChI:InChI=1/C5H5N3/c1-2-7-8-4-3-6-5(1)8/h1-4,6H

Upstream product

• 135829-81-1 5-amino-1-(2,2-diethoxyethyl)-pyrazole-4-carboxylic acid 
• 222055-80-3 5-amino-1-(2,2-diethoxy-ethyl)-1H-pyrazole-4-carboxylic acid ethyl ester 
• 135829-73-1 1-(2,2-diethoxyethyl)-5-aminopyrazole 

Downstream Products

• 188998-04-1 1-formyl-1H-imidazo[1,2-b]pyrazole 
• 135830-23-8 1-acetyl-1H-imidazo[1,2-b]-pyrazole 

Relevant academic research and scientific papers

Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof

Compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and at least one bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing compounds having a ring junction nitrogen and an N-hydroxy or N-amino group and derivatives thereof. A method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.

Methods of dyeing keratin fibers with compositions containing pyrazolo-azole couplers

The present invention relates to a composition for dyeing keratinous fibers, especially human hair, which in a medium appropriate for dyeing comprises: as coupler at least one compound of formula: ?in which: R1is especially hydrogen, alkyl, aryl, a heterocycle, a halogen, etc.; R2is especially hydrogen, halogen, aryloxy, alkoxy, acyloxy, arylthio, alkylthio, heteroarylthio, heteroaryloxy, etc.; Za, Zband Zcare independently a nitrogen atom or a carbon which carries a radical R3or R4whose meanings are identical to those of R1; at least one of Za, Zband Zcis a nitrogen atom; and R3and R4may together form an unsubstituted or substituted aromatic ring; and at least one oxidation base.

Synthesis of mono- and disubstituted 1H-imidazo[1,2-b]pyrazoles

The improved synthesis of 1H-imidazo[1,2-b]pyrazole 1 and of mono- and disubstituted derivatives is described and representative experimental procedures are given. Namely, 2-, 3-, 7- and 6-monosubstituted (2-15k), 2,3- and 6,7-disubstituted (16,17) compounds are prepared and characterized.

Studies on 3'-quaternary ammonium cephalosporins - III. Synthesis and antibacterial activity of 3'-(3-aminopyrazolium)cephalosporins

The synthesis and in vitro antibacterial activity of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] cephalosporins bearing N-mono or dialkyl and carbamoyl aminopyrazolium, and five- or six-membered rings fused to the 3-aminopyrazolium methyl groups at the 3-position, are described. Aminopyrazolium methyl cephalosporins (23e, f, i), with fused saturated and unsaturated rings were especially effective against Staphylococcus strains compared to 3-amino-2-methylpyrazolium methyl cephalosporin (1). Among the cephalosporins prepared in this work, 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino acetamidol-3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a] pyrimidinio)methyl-3-cephem-4-carboxylate (23f) showed a good balance of antibacterial activity against both Gram-positive bacteria including Staphylococcus aureus and Gram-negative bacteria including P. aeruginosa. An imidazopyrazolium group at the 3-position in, for example, cephalosporin (23i) was particularly effective for improving antibacterial activity against MRSA.

Synthesis of novel derivatives of 1H-imidazo[1,2-b]pyrazole as potential CNS-agents

As part of a preliminary study on novel 5-HT3 ligands, the synthesis of a series of 1H-imidazo[1,2-b]-pyrazole derivatives is described. The bicyclic heteroaromatic nucleus was functionalized as positions 1, 6 and 7 to give the series of tropanyl derivatives 4a-g, 12a, 12d. Different synthetic approaches were utilized to obtain the desired molecules: endo and exo 6-amides 4a, 12a and 6-ester 4b required two independent schemes due to the opposite behavior of the intermediate imidazolide 3 towards tropine and tropanamine. The 7-congeners, ester 4c, its tropinium salt 4e, the endo and exo amides 4d and 12d were prepared from the known common precursor 8, while derivatives 4f-g, originated by functionalizing position 1, were obtained from 1H-imidazo[1,2-b]pyrazole by direct N-acylation. Since the structural features of these molecules seemed to meet the main rules of the S.A.R. studies published so far, they were evaluated 'in vitro' for 5-HT3 receptor affinity. The biochemical data show significant activity for derivatives 4a-e, 4g. These results are encouraging and justify further investigational work on this class of molecules.

Cephem compounds

Cephem compounds of the following formula are disclosed: STR1 wherein R1 is amino or protected amino group. R2 is H or an organic group, R3 is H or an organic group, R4 is H, lower alkyl, carboxy, protected carb