222292-69-5

Basic information

• Product Name: 1,2-dihydro-2-oxo-Imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester
• Synonyms: 1,2-dihydro-2-oxo-Imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester;Ethyl 2-Hydroxyimidazo[1,5-A]Pyrimidine-8-Carboxylate;Ethyl 2-Hydroxyimidazo[1,5-A]Pyrimidine-8-Carboxylate(WX141993)
• CAS NO: 222292-69-5
• Molecular Formula: C9H9N3O3
• Molecular Weight: 207.18606
• Mol File: 222292-69-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-dihydro-2-oxo-Imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dihydro-2-oxo-Imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester(222292-69-5)
• EPA Substance Registry System: 1,2-dihydro-2-oxo-Imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester(222292-69-5)

Safety Data

• Hazardous Substances Data: 222292-69-5(Hazardous Substances Data)

Usage

Chemical class

Heterocyclic compound

Structure

Ester derivative of pyrimidine-8-carboxylic acid with an ethyl group attached to the carboxylic acid functional group

Molecular weight

216.18 g/mol

Appearance

Solid or crystalline

Solubility

Soluble in organic solvents such as DMSO, ethanol, and methanol

Stability

Stable under normal laboratory conditions

Pharmacological activities

Potential anti-cancer and anti-inflammatory properties

Applications

Used in medicinal chemistry and drug development as a research reagent

Purpose

To study biological properties and design new pharmaceuticals with improved efficacy and safety profiles

Upstream product

• 21190-16-9 5-amino-1H-imidazole-4-carboxylic acid ethyl ester 
• 222292-65-1 2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxopyrrolidin-1-yloxy)acrylate 

Downstream Products

• 1250998-26-5 ethyl 2-chloroimidazo[1,5-a]pyrimidine-8-carboxylate 
• 1431654-63-5 ethyl 2-(2-(trifluoromethyl)phenyl)imidazo[1,5-a]pyrimidine-8-carboxylate 
• 1431654-64-6 2-(2-(trifluoromethyl)phenyl)imidazo[1,5-a]pyrimidine-8-carboxylic acid 
• 1431647-28-7 N-(pyridin-3-yl)-2-(2-(trifluoromethyl)phenyl)imidazo[1,5-a]pyrimidine-8-carboxamide 
• 1431654-65-7 2-(2-(trifluoromethyl)phenyl)imidazo[1,5-a]pyrimidin-8-amine 
• 1431647-32-3 N-(2-(2-(trifluoromethyl)phenyl)imidazo[1,5-a]pyrimidin-8-yl)picolinamide 

Relevant articles and documents

SUBSTITUTED BICYCLIC AZA-HETEROCYCLES AND ANALOGUES AS SIRTUIN MODULATORS

Provided herein are novel substituted bicyclic aza-heterocycle sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

Synthesis of 2,8-disubstituted imidazo[1,5-a]pyrimidines with potent antitumor activity

Seventeen 1,2,3,4-tetrahydroimidazo[1,5-a]pyrimidine derivatives bearing electron-withdrawing substituents were designed and synthesized by novel ring closure as potential antitumor agents. They were screened for their activities against mouse leukemia L1210 and human oral epidermoid carcinoma KB cell lines, and relationships of structure and antitumor activity in vitro are discussed. It was found that 8-thiocarbamoyl-1,2,3,4- tetrahydroimidazo[1,5-α]pyrimidin-2(1H)-thione (8c) exhibited activity comparable to that of 5-fluorouracil against both L1210 and KB cells. The existence of both 2-thioxo and 8-substituent with a thioxo group in the molecule is crucial for the cytotoxicity against L1210 and KB cells. A novel procedure for introduction of a double bond between C-3 and C-4 in 8c was developed. Introduction of the 3,4-double bond increased the activity against L1210, but against KB cells the activity decreased by 4-fold. Cytotoxicity of compounds 8c and 8-thiocarbamoyl-1,2-dihydroimidazo[1,5-α]pyrimidin-2(1H)- thione (11c) against human solid tumor and leukemia cell lines was further evaluated. The saturation of the 3,4-double bond led to a significant increase in cytotoxicity against tumor cell lines tested.