64951-07-1

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE is used as an intermediate in the synthesis of various pharmaceutical compounds for its potential therapeutic applications.
Used in Organic Chemistry:
ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE is used as a building block for the synthesis of other complex molecules, contributing to the development of new chemical entities with potential applications in various fields.

InChI:InChI=1/C9H9N3O2/c1-2-14-8(13)7-6-11-9-10-4-3-5-12(7)9/h3-6H,2H2,1H3

Upstream product

• 109-12-6 2-aminopyrimidine 
• 70-23-5 ethyl Bromopyruvate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 105-36-2 ethyl bromoacetate 
• 623-47-2 propynoic acid ethyl ester 
• 100422-78-4 ethyl 5-oxo-2-(pyrimidin-2-yl)-2,5-dihydroisoxazole-4-carboxylate 

Downstream Products

• 149520-94-5 2-amino-1H-imidazole-4-carboxylic acid ethyl ester 
• 64951-11-7 imidazo[1,2-a]pyrimidine-3-carboxylic acid 

Relevant academic research and scientific papers

Discovery of potent colony-stimulating factor 1 receptor inhibitors by replacement of hinge-binder moieties

Tumor-associated macrophages (TAMs) are predominantly associated with tumor growth. Colony-stimulating factor 1 receptor (CSF1R) acts as a key regulator of TAM survival and differentiation and is a molecular target for cancer therapies. Herein, novel CSF1

New geldanamycin derivatives with anti Hsp properties by mutasynthesis

Mutasynthetic supplementation of the AHBA blocked mutant strain of S. hygroscopicus, the geldanamycin producer, with 21 aromatic and heteroaromatic amino acids provided new nonquinoid geldanamycin derivatives. Large scale (5 L) fermentation provided four new derivatives in sufficient quantity for full structural characterisation. Among these, the first thiophene derivative of reblastatin showed strong antiproliferative activity towards several human cancer cell lines. Additionally, inhibitory effects on human heat shock protein Hsp90α and bacterial heat shock protein from H. pylori HpHtpG were observed, revealing strong displacement properties for labelled ATP and demonstrating that the ATP-binding site of Hsps is the target site for the new geldanamycin derivatives.

THERAPEUTIC INHIBITORY COMPOUNDS

Provided herein are heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds that are useful for inhibiting plasma kallikrein. Furthermore, the subject compounds and compositions are useful for the treatment of diseases wherein the inhibition of plasma kallikrein inhibition has been implicated, such as angioedema and the like.

Hypervalent iodine(III) promoted direct synthesis of imidazo[1,2-a] pyrimidines

An efficient and mild synthesis of imidazo[1,2-a]pyrimidine derivatives has been developed from readily available pyrimidyl arylamines or enamines through a hypervalent iodine-promoted intramolecular C-H bond cycloamination reaction. This protocol allows for the facile construction of biologically active bicyclic imidazo[1,2-a]pyrimidine skeletons as well as other imidazo[1,2-a]-type fused heterocycles.

Discovery of 6-(Aminomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2- α]pyrimidine-2-carboxamides as potent, selective dipeptidyl peptidase-4 (DPP4) inhibitors

Continued structure-activity relationship (SAR) exploration within our previously disclosed azolopyrimidine containing dipeptidyl peptidase-4 (DPP4) inhibitors led us to focus on an imidazolopyrimidine series in particular. Further study revealed that by replacing the aryl substitution on the imidazole ring with a more polar carboxylic ester or amide, these compounds displayed not only increased DPP4 binding activity but also significantly reduced human ether-à-go-go related gene (hERG) and sodium channel inhibitory activities. Additional incremental adjustment of polarity led to permeable molecules which exhibited favorable pharmacokinetic (PK) profiles in preclinical animal species. The active site binding mode of these compounds was determined by X-ray crystallography as exemplified by amide 24c. A subsequent lead molecule from this series, (+)-6-(aminomethyl)-5-(2,4-dichlorophenyl)-N-(1-ethyl-1H- pyrazol-5-yl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxamide (24s), emerged as a potent, selective DPP4 inhibitor that displayed excellent PK profiles and in vivo efficacy in ob/ob mice.

AZOLOPYRIMIDINE-BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV AND METHODS

Compounds are provided having the formula (I): Formula (I) wherein R, X, Y, A and n are as defined herein.

The Chemistry of 5-Oxodihydroisoxazoles. VIII. Photolysis of 2-(Heterocyclyl)isoxazol-5(2H)-ones

Photolysis of 2-(heterocyclyl)isoxazol-5(2H)-ones occurs readily at 300 nm.In alcohol the products are the corresponding 2-alkoxy-3-heterocyclylaminoacrylates, and, in the presence of 1 M trifluoroacetic acid, the corresponding imidazole annulated heteroc

Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazopyrimidine derivatives

The synthesis of a group of imidazopyrimidine-2-carboxylic esters, acids and amides is described.The structures of the new compounds are supported by 1H- and 13C-NMR spectra.These compounds were tested in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic action.The ester 5b, the acid 6c and the amide 7a showed antiinflammatory action in the rat paw edema (ca. 1/3 x indomethacin), while almost all compounds displayed significant analgesic activity in the acetic acid writhing test, particularly the 5-chloro-7-methyl derivatives 5a, 6a and 7a (ca 1/5 x indomethacin).All new compounds were found to be lacking in inhibitory activity on cyclooxygenase in vitro. imidazopyrimidines / antiinflammatory activity / analgesic activity / ulcerogenic activity / cyclooxygenase inhibition

The chemistry of 5-oxodihydroisoxazoles VII1 conversion of heterocyclylisoxazol-5(2H)-ones to imidazoles by flash vacuum pyrolysis

A number of 5-oxo-2,5-dihydroisoxazoles, substituted with nitrogen heterocycles at N-2, have been subjected to flash vacuum pyrolysis. Annelated imidazoles are obtained in excellent yields, and are presumed to arise by intramolecular cyclisation of an imi

Antifungal activity in vitro of some imidazopyrimidine derivatives

In regard to fungicidal activity of imidazole ring found in chemical compounds such as econazole, a series of 42 diversely substituted imidazopyrimidines was synthetized and examined for its antifungal activity in several species.