149520-94-5

Basic information

• Product Name: 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)
• Synonyms: 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI);ethyl 2-amino-1H-imidazole-5-carboxylate(SALTDATA: FREE);1H-IMidazole-5-carboxylic acid, 2-aMino-, ethyl ester;Ethyl 2-AMinoiMidazole-5-carboxylate;Ethyl 2-aMino-1h-iMidazole-4-carboxylate;1H-IMidazole-4-carboxylicacid,2-aMino-,ethylester;ETHYL 2-AMINO-1H-IMIDAZOLE-(4)5-CARBOXYLATE;2-amino-1H-Imidazole-5-carboxylic acid ethyl ester
• CAS NO: 149520-94-5
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.16
• Product Categories: CARBOXYLICESTER
• Mol File: 149520-94-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 363.632 °C at 760 mmHg
• Flash Point: 173.719 °C
• Appearance: /
• Density: 1.319 g/cm³
• Vapor Pressure: 1.78E-05mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 12.21±0.10(Predicted)
• CAS DataBase Reference: 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)(149520-94-5)
• EPA Substance Registry System: 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)(149520-94-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 149520-94-5(Hazardous Substances Data)

Usage

General Description

1H-Imidazole-4-carboxylic acid, 2-amino-, ethyl ester (9CI) is a chemical compound with the molecular formula C6H8N2O2. It is an ethyl ester derivative of the amino acid histidine. 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI) has a heterocyclic structure and is commonly used in the synthesis of pharmaceuticals and agricultural chemicals. It has been investigated for its potential biological activities, including its role as an antifungal agent and as a precursor in the synthesis of histidine-rich polypeptides. Additionally, 1H-Imidazole-4-carboxylic acid, 2-amino-, ethyl ester (9CI) has been studied for its potential applications in the development of functional materials and biomaterials.

InChI:InChI=1/C6H9N3O2/c1-2-11-5(10)4-3-8-6(7)9-4/h3H,2H2,1H3,(H3,7,8,9)

Upstream product

• 64951-07-1 ethyl imidazo<1,2-a>pyrimidine-3-carboxylate 
• 109-12-6 2-aminopyrimidine 
• 70-23-5 ethyl Bromopyruvate 
• 64951-06-0 ethyl imidazo<1,2-a>pyrimidine-2-carboxylate 

Downstream Products

• 1239584-19-0 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate 
• 1258386-07-0 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate 

Relevant articles and documents

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.

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.