860725-77-5

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 

Downstream Products

• 1185843-41-7 (5R)-5-(2-hydroxy-3-methoxyphenyl)-1',3',7-trimethyl-3,3a,5,6-tetrahydro-2H,2'H-spiro[1-benzothiophene-4,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione 1,1-dioxide 
• 1185843-42-8 (5S)-5-(2-hydroxy-3-methoxyphenyl)-1',3',7-trimethyl-3,3a,5,6-tetrahydro-2H,2'H-spiro[1-benzothiophene-4,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione 1,1-dioxide 

Relevant academic research and scientific papers

“On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids

A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using “on water” concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086?M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method.

5-Arylidene N,N-dimethylbarbiturates as urease inhibitors

Earlier 5-arylidene N,N-dimethylbarbiturates 1-24 were reported by our group as novel antioxidant, nevertheless, urease inhibitory activity of these compounds has not been investigated at all. In the present study, compounds 1-24 were synthesized by the reaction of N,N-dimethylbarbituric acid with different aromatic aldehydes, and screened for their in vitro urease inhibitory effects. Compound 7, was found to be most active urease inhibitor in the series. Nonetheless, compounds 11, 12, and 19 were also active against urease enzyme.

Antibacterial and antifungal activities of 5-arylidene-N,N-dimethylbarbiturates derivatives

A series of N,N-dimethyl-arylidene barbiturates 1-22 has been re-synthesized and evaluated against a number of Gram-positive, Gram-negative bacteria and some fungal strains. Most of the compounds were found to be active against a number of Gram-positive, Gram-negative and also displayed anti-fungal activities.

Xanthine oxidase inhibition by 5-aryledene N,N'-dimethylbarbituric acid derivatives

N,N'-dimethylbarbituric acid derivatives 1-24 were evaluated for their xanthine oxidase (XO) inhibitory activity. Majority of these compounds showed a good to moderate in vitro xanthine oxidase inhibitory activity (IC50 = 20.97 ± 0.29 - 327.0 ± 3.50 μM), while eight compounds were found to be completely inactive. A structure-activity relationship has been discussed, identifying structural features, responsible for varying degree of activity.

Synthesis and DPPH radical scavenging activity of 5-arylidene-N, Ndimethylbarbiturates

Twenty-four derivatives of N,N-dimethylbarbituric acid 1-24 were screened for their DPPH radical scavenging activity. These compounds showed an excellent antioxidant activity. A structure-activity relationship has been discussed, while all the synthetic compounds were characterized by spectroscopic techniques and elemental analysis.

Diels-alder reactions with cyclic sulfones: VIII. Organic catalysis in the synthesis of spiro[1-benzothiophene-4,5′-pyrimidine]-2′,4′, 6′-trione 1,1-dioxides and 2′-thioxospiro[1-benzothiophene-4, 5′-pyrimidine]-4′,6′-dione 1,1-dioxides

5-Isopropenyl-2,3-dihydrothiophene 1,1-dioxide reacted with 5-methylidenepyrimidine-2,4,6-triones and 5-methylidene-2-thioxopyrimidine-4,6- diones in the presence of chiral amines or amino acids with high regio- and stereoselectivity to give optically active derivatives of barbituric and thiobarbituric acids spirofused at the 5-position to 1-benzothiophene 1,1-dioxide fragment. The reaction of 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide with 5-(2-methoxybenzylidene)-2-thioxopyrimidine-4,6-dione (generated in situ from 2-methoxybenzaldehyde and thiobarbituric acid) in the presence of (-)-ephedrine or L-4-(tert-butyldimethylsiloxy) proline gave the corresponding 2-thioxospiro[1-benzothiophene-4,5′-pyrimidine]-4′, 6′-dione 1,1-dioxide with an enantiomeric excess of 80%.