60045-65-0

Basic information

• Product Name: 4,6(1H,5H)-Pyrimidinedione, dihydro-5-[(2-nitrophenyl)methylene]-2-thioxo-
• Synonyms: 5-(2-nitro-benzylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione;5-o-Nitrobenzylidene-2-thiobarbituric acid;5-(2-nitro-benzylidene)-2-thio-barbituric acid;5-(2-Nitro-benzyliden)-2-thio-barbitursaeure
• CAS NO: 60045-65-0
• Molecular Formula: C11H7N3O4S
• Molecular Weight: 277.26
• Mol File: 60045-65-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4,6(1H,5H)-Pyrimidinedione, dihydro-5-[(2-nitrophenyl)methylene]-2-thioxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6(1H,5H)-Pyrimidinedione, dihydro-5-[(2-nitrophenyl)methylene]-2-thioxo-(60045-65-0)
• EPA Substance Registry System: 4,6(1H,5H)-Pyrimidinedione, dihydro-5-[(2-nitrophenyl)methylene]-2-thioxo-(60045-65-0)

Safety Data

• Hazardous Substances Data: 60045-65-0(Hazardous Substances Data)

Upstream product

• 504-17-6 4,6-dihydroxy-2-mercaptopyrimidine 
• 552-89-6 2-nitro-benzaldehyde 

Relevant articles and documents

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Barbituric and thiobarbituric acid derivatives have become progressively attractive to medicinal chemists due to their wide range of biological activities. Herein, different series of 1,3,5-trisubstituted barbiturates and thiobarbiturates were prepared in moderate to excellent yields and their activity as xanthine oxidase inhibitors, antioxidants, antibacterial agents and as anti-proliferative compounds was evaluated in vitro. Interesting bioactive barbiturates were found namely, 1,3-dimethyl-5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6c) and 1,3-dimethyl-5-[1-[2-(4-nitrophenyl)hydrazinyl]ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6e), which showed concomitant xanthine oxidase inhibitory effect (IC50 values of 24.3 and 27.9 μM, respectively), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (IC50 values of 18.8 and 23.8 μM, respectively). In addition, 5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6d) also revealed DPPH radical scavenger effect, with an IC50 value of 20.4 μM. Moreover, relevant cytotoxicity against MCF-7 cells (IC50 = 13.3 μM) was observed with 5-[[(2-chloro-4-nitrophenyl)amino]methylene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (7d). Finally, different 5-hydrazinylethylidenepyrimidines revealed antibacterial activity against Acinetobacter baumannii (MIC values between 12.5 and 25.0 μM) which paves the way for developing new treatments for infections caused by this Gram-negative coccobacillus bacterium, known to be an opportunistic pathogen in humans with high relevance in multidrug-resistant nosocomial infections. The most promising bioactive barbiturates were studied in silico with emphasis on compliance with the Lipinski's rule of five as well as several pharmacokinetics and toxicity parameters.

Composition for trichogenousness

The present invention relates to novel barbiturate and thiobarbiturate derivatives and a composition for promoting hair growth using the same. According to the present invention, the barbiturate and thiobarbiturate derivatives, in an animal model, have shown to promote hair growth and have excellent effects on hair growth by promoting regulation of Wnt/andbeta;-catenin and hair growth factor signaling and suppressing mechanism of apoptosis. Accordingly, the barbiturate and thiobarbiturate derivatives of the present invention may be used as a composition for promoting hair growth.COPYRIGHT KIPO 2017

Facile syntheses of bioactive 5-arylidenethiobarbituric acids

A simple and green chemistry route for the preparation of 5-arylidenethiobarbituric acids has been developed by Knoevenagel condensation of thiobarbituric acid with different aromatic and heteroaromatic aldehydes using catalytic amount of acetic acid by g