159181-78-9

Basic information

• Product Name: 1H-Imidazo[1,2-b]pyrazole-6-carboxylicacid(9CI)
• Synonyms: 1H-Imidazo[1,2-b]pyrazole-6-carboxylicacid(9CI);1H-pyrazolo[1,5-a]imidazole-6-carboxylic acid
• CAS NO: 159181-78-9
• Molecular Formula: C6H5N3O2
• Molecular Weight: 151.12
• Product Categories: CARBOXYLICACID;GLYCINESCAFFOLD
• Mol File: 159181-78-9.mol

Chemical Properties

• Appearance: /
• Density: 1.741g/cm³
• Refractive Index: 1.793
• CAS DataBase Reference: 1H-Imidazo[1,2-b]pyrazole-6-carboxylicacid(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazo[1,2-b]pyrazole-6-carboxylicacid(9CI)(159181-78-9)
• EPA Substance Registry System: 1H-Imidazo[1,2-b]pyrazole-6-carboxylicacid(9CI)(159181-78-9)

Safety Data

• Hazardous Substances Data: 159181-78-9(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic compound

Structure

Fused imidazole and pyrazole ring system, carboxylic acid functional group

Pharmacological properties

Potential building block for synthesis of bioactive molecules, potential drug activity

Importance

Unique structural features, potential biological activities, further study and applications in pharmaceutical and medical industries.

InChI:InChI=1/C6H5N3O2/c10-6(11)4-3-5-7-1-2-9(5)8-4/h1-3,7H,(H,10,11)

Upstream product

• 222056-28-2 ethyl 1-(2,2-diethoxyethyl)-5-aminopyrazole-3-carboxylate 
• 159181-77-8 ethyl imidazo<1,2-b>pyrazole-6-carboxylate 

Relevant articles and documents

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.

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.