14077-84-0

Basic information

• Product Name: 5-heptylpyrimidine-2,4,6(1H,3H,5H)-trione
• CAS NO: 14077-84-0
• Molecular Formula: C₁₁H₁₈N₂O₃
• Molecular Weight: 226.2722
• Mol File: 14077-84-0.mol
• Article Data: 3

Chemical Properties

• Density: 1.087g/cm³
• Refractive Index: 1.469
• CAS DataBase Reference: 5-heptylpyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-heptylpyrimidine-2,4,6(1H,3H,5H)-trione(14077-84-0)
• EPA Substance Registry System: 5-heptylpyrimidine-2,4,6(1H,3H,5H)-trione(14077-84-0)

Safety Data

• Hazardous Substances Data: 14077-84-0(Hazardous Substances Data)

Upstream product

• 607-83-0 diethyl heptylmalonate 
• 57-13-6 urea 
• 67-52-7 BARBITURIC ACID 
• 111-71-7 heptanal 
• 124-19-6 nonan-1-al 
• 71934-34-4 5-heptylidene-pyrimidine-2,4,6-trione 

Relevant articles and documents

Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones

Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.

INFLUENCE DE LA LIPOPHILIE SUR L'OXYDATION BIOLOGIQUE D'UNE CHAINE METHYL-3 BUTYLE EN SERIE BARBITURIQUE

Influence of lipophilicity on biological oxidation of a 3-methylbutyl side chain in a barbiturate series.The lipophilic character of 5-methyl-5-(3-methylbutyl) barbituric acid 3 is lower (Δ logP=0.5) than that of amobarbital, itself lower (Δ logP=0.5) than that of 5-(3-methylbutyl)-5-propyl barbituric acid.The influence of these differences upon biological oxidation was studied.Models of various potential metabolites of 3 were synthesized and compound 3 was administered to rats and dogs. 6.4percent (dogs) or 5.3percent (rats) of non-modified compound 3 and 53.1percent (dogs) or 59.6percent (rats) of a γ-hydroxylated metabolite were recorved in urine.These results compared with those obtained for related compounds show that the influence of lipophilicity upon biological oxidation is not as important as one could suppose.Keywords - lipophilicity / metabolism / barbiturates / chromic oxidation / biological hydroxylation / hydroxybarbiturates