331839-72-6

Basic information

• Product Name: 2(1H)-Pyrimidinone,5-acetyl-3,4-dihydro-4-(3-hydroxyphenyl)-6-methyl-(9CI)
• Synonyms: 2(1H)-Pyrimidinone,5-acetyl-3,4-dihydro-4-(3-hydroxyphenyl)-6-methyl-(9CI)
• CAS NO: 331839-72-6
• Molecular Formula: C13H14N2O3
• Molecular Weight: 246.26186
• Product Categories: BIGNELLI
• Mol File: 331839-72-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(1H)-Pyrimidinone,5-acetyl-3,4-dihydro-4-(3-hydroxyphenyl)-6-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Pyrimidinone,5-acetyl-3,4-dihydro-4-(3-hydroxyphenyl)-6-methyl-(9CI)(331839-72-6)
• EPA Substance Registry System: 2(1H)-Pyrimidinone,5-acetyl-3,4-dihydro-4-(3-hydroxyphenyl)-6-methyl-(9CI)(331839-72-6)

Safety Data

• Hazardous Substances Data: 331839-72-6(Hazardous Substances Data)

Usage

Chemical Class

Pyrimidinone derivatives

Structure

Pyrimidinone ring with an acetyl group at position 5, a hydroxyl group at position 3, a methyl group at position 6, and a phenyl group attached to position 4

Usage

Key intermediate in the synthesis of pharmaceutical compounds

Potential Applications

Medicinal chemistry, development of new drugs or chemical entities with therapeutic properties

Biological Activities

Not fully elucidated, but has potential to exhibit various activities

Pharmacological Properties

Not fully elucidated, but structural features make it a promising candidate for further research and development in the pharmaceutical industry.

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 57-13-6 urea 
• 123-54-6 acetylacetone 

Relevant articles and documents

Exploiting silver trifluoromethanesulfonate as efficient and reusable catalyst for the synthesis of dihydropyrimidine derivatives under different reaction environments

Different results were generated under different reaction conditions for the multicomponent reactions. Herein, an efficiently improved and mild protocol for the synthesis of dihydropyrimidine derivatives using cheap silver trifluoromethanesulfonate (CFsu

Design, synthesis, in-vitro thymidine phosphorylase inhibition, in-vivo antiangiogenic and in-silico studies of C-6 substituted dihydropyrimidines

Thymidine phosphorylase (TP) is an angiogenic enzyme. It plays an important role in angiogenesis, tumour growth, invasion and metastasis. In current research work, we study the effect of structural modification of dihydropyrimidine-2-ones (DHPM-2-ones) on TP inhibition. A series of eighteen new derivatives of 3,4-dihydropyrimidone-2-one were designed and synthesized through the structural modification at C-6 position. All these new derivatives were then assessed for in-vitro inhibition of thymidine phosphorylase (TP) from E. coli. Oxadiazole derivatives 4a-e exhibited excellent TP-inhibition at low micromolar concentration levels better than standard drug 7-deazaxanthine (7-DX). Among all these compounds, 4b was found to be the most potent with IC50 = 1.09 ± 0.004 μM. Anti-angiogenesis potential of representative compounds were also studied in a chorioallantoic membrane (CAM) assay. Here again, compound 4b was found to be the potent anti-angiogenesis compound in a CAM assay. Docking studies were also performed with Molecular Operating Environment (MOE) to further analyse the mode of inhibition of these compounds. Binding mode analysis of the most active inhibitors showed that these are well accommodated into the binding site of enzyme though stable hydrogen bonding and hydrophobic interactions.

Phenols catalyzed Biginelli reactions: A self catalyzed monastrol protocol

A simple and efficient approach towards one step synthesis of various dihydropyrimidones and thiones (Biginelli reaction) was developed by using phenols as catalysts. The multicomponent reaction was conducted between aromatic aldehydes, active methylenes

Ionic liquid effect over the biginelli reaction under homogeneous and heterogeneous catalysis

Bronsted and Lewis acid catalysts with ionic tags under homogeneous and heterogeneous conditions have been tested to perform the Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-one (DHPMs). Metal-containing ionic liquids were evaluated as the catalysts

Ultrasound-mediated synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (or Thiones) with NaHSO4·H 2O

A fast and efficient Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)- ones (or thiones) by the reaction of aromatic aldehydes, β-dicarbonyls, and urea/thiourea using NaHSO4·H2O/ultrasound system is presented. The reactions were ca

The biginelli reaction with an imidazolium-tagged recyclable iron catalyst: Kinetics, mechanism, and antitumoral activity

The present work describes the synthesis, characterization, and application of a new ion-tagged iron catalyst. The catalyst was employed in the Biginelli reaction with impressive performance. High yields have been achieved when the reaction was carried ou

Mechanistic studies on Lewis acid catalyzed Biginelli reactions in ionic liquids: Evidence for the reactive intermediates and the role of the reagents

This paper describes the use of common Lewis acids supported in imidazolium-based ionic liquids as the catalysts to promote the Biginelli reaction. The ionic liquid effect and the reaction mechanism are discussed on the basis of nuclear magnetic resonance

Synthesis of some substituted 2-oxo-1,2,3,4-tetrahydropyrimidines (3,4-dihydropyrimidin-2(1H)-ones) and 2-thioxo-1,2,3,4-tetrahydropyrimidines, catalyzed by tin(II) chloride dihydrate and tin (II) iodide under microwave irradiation

A simple, economic and efficient one pot synthesis of some substituted 2-oxo-1,2,3,4-tetrahydropyrimidines [3,4-dihydropyrimidin-2 (1H)-ones) and 2-thioxo-1,2,3,4-tetrahydropyrimidines under solvent free condition and microwave irradiation catalyzed by ti

Method of screening compounds

The present invention is directed to a novel, target-blind approach to drug discovery. The concept is to model human phenotypes in a teleost, such as a zebrafish, and then screen compounds, e.g., small molecules, for their ability to alter the phenotype.