99933-98-9

Upstream product

• 35221-12-6 1,3-diphenyl-2-thiobarbituric acid 
• 552-89-6 2-nitro-benzaldehyde 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 102-08-9 N,N-diphenylthiourea 

Downstream Products

• 100671-75-8 3-(2-Nitro-phenyl)-5,7-diphenyl-6-thioxo-2,5,6,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 100671-85-0 3-(2-Nitro-phenyl)-5,7-diphenyl-6-thioxo-6,7-dihydro-5H-isoxazolo[3,4-d]pyrimidin-4-one 

Relevant academic research and scientific papers

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.

A synthetic route to novel 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio)barbiturates

2,1-Benzisoxazoles, also called anthranils, are one of the two types of aromatic bicyclic heterocycles having a benzene ring fused with an isoxazole, which are particularly recognized as valuable intermediates in organic synthesis. Nevertheless several methods can be found in the literature to prepare 2,1-benzisoxazoles, we herein report a new, efficient, simple, mild, and alternative procedure to prepare 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)barbiturates in moderate to good yields (51–82%). All the novel benzisoxazoles showed spectral data fully consistent with the assigned structures, which were unequivocally confirmed by single crystal X-ray analysis. A possible mechanism of the reaction is proposed. In addition, a screening of the bioactivity of these benzisoxazoles as xanthine oxidase inhibitors, antioxidants, and cytotoxic compounds was performed. The benzisoxazole formed from barbituric acid revealed moderate xanthine oxidase inhibitory effects (IC50 = 22.10 μM).

Synthesis and antimicrobial activity of 1,3,5-triaryl-10-benzyl- 1,2,3,4,6,7,8,9-octahydro-8,8-dimethyl-4,6-dioxo-2-thioxo-5H, 10H- pyrimido[4,5-b]quinolines

A convenient one pot synthesis of some pyrimido[4,5-b]quinoline derivatives 2a-g and 3a-g has been reported by the condensation of 5,5- dimethyl-3-benzylamino-2-cyclohexen-1-one with appropriate arylaldehydes and 1,3-diaryl-2-thiobarbituric acids in metha

One-pot Syntheses of 5-Oxo-1,4,5,6,7,8-hexahydro-quinolines and Pyrimido,4,5-b>quinolines using Microwave Irradiation and Ultrasound

A mild and convenient method for the synthesis of alkyl 4-aryl-1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxoquinoline-3-carboxylates (4a-f) and (6a-g) by the condensation of 5,5-dimethylcyclohexane-1,3-dione (1) and aromatic aldehydes (2a-g) with methyl β-a

Synthesis of Pyrazolopyrimidines and Isoxazolopyrimidines

The arylidene derivatives (2), prepared from 1,3-diphenylthiobarbituric acid (1) and substituted aldehydes, on condensation with hydrazine hydrate, phenylhydrazine and hydroxylamine give 3-aryl-5,7-diphenyl-6-thiopyrazolopyrimidin-4-(5H,7H)-ones (7

Synthesis of Some Pyridopyrimidines

The synthesis of some pyridopyrimidines (1) using N-phenacylpyridinium bromide and ammonium acetate is reported.These compounds have been tested for their insecticidal and herbicidal activities and found to be inactive.