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King, S. Bruce; Stratford, Eugene S.; Craig, Charles R.; Fifer, E. Kim

doi:10.1023/a:1016236615559

Cited by 31 publications

(10 citation statements)

References 10 publications

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“…The majority of the products obtained are spirocyclic barbiturates, which are of interest given the well-established medicinal importance of the barbiturate motif, and the biological activity of structurally related spirocycles (Figure 1 ). [ 10 ]…”

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confidence: 99%

All‐Carbon [3+3] Oxidative Annulations of 1,3‐Enynes by Rhodium(III)‐Catalyzed CH Functionalization and 1,4‐Migration

et al. 2015

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confidence: 99%

All‐Carbon [3+3] Oxidative Annulations of 1,3‐Enynes by Rhodium(III)‐Catalyzed CH Functionalization and 1,4‐Migration

et al. 2015

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“…Therefore, the special orientation of the functional substituents facilitates the recognition of bioactive targets [30]. Spirobarbiturates have the special attention of the pharmaceutical community due to their broad spectrum of biological properties [31]. They exhibit useful neuropharmacological effects [32].…”

Section: Introductionmentioning

confidence: 99%

Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase

et al. 2021

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A continuously growing interest in convenient and ‘green’ reaction techniques encourages organic chemists to elaborate on new synthetic methodologies. Nowadays, organic electrochemistry is a new useful method with important synthetic and ecological advantages. The employment of an electrocatalytic methodology in cascade reactions is very promising because it provides the combination of the synthetic virtues of the cascade strategy with the ecological benefits and convenience of electrocatalytic procedures. In this research, a new type of the electrocatalytic cascade transformation was found: the electrochemical cyclization of 1,3-dimethyl-5-[[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](aryl)methyl]pyrimidine-2,4,6(1H,3H,5H)-triones was carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of spiro[furo[3,2-b]pyran-2,5′-pyrimidines] in 59-95% yields. This new electrocatalytic process is a selective, facile, and efficient way to create spiro[furo[3,2-b]pyran-2,5′-pyrimidines], which are pharmacologically active heterocyclic systems with different biomedical applications. Spiro[furo[3,2-b]pyran-2,5′-pyrimidines] were found to occupy the binding pocket of aldose reductase and inhibit it. The values of the binding energy and Lead Finder’s Virtual Screening scoring function showed that the formation of protein–ligand complexes was favorable. The synthesized compounds are promising for the inhibition of aldose reductase. This makes them interesting for study in the treatment of diabetes or similar diseases.

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“…Several spiro-(thio)barbituric acid derivatives in which the active methylene carbon of (thio)barbituric acid is substituted by an unsubstituted cyclobutane or cyclohexane ring [32,33] have been synthesized, but no pharmacological data is obtained with these compounds. Spiro compounds have been reported to possess biological activities that include anti-inflammatory activity [34], anticonvulsant, CNS depressant [35], narcotic [36], hypotensive, analgesic [37].…”

Section: Introductionmentioning

confidence: 99%

“…Spiro compounds have been reported to possess biological activities that include anti-inflammatory activity [34], anticonvulsant, CNS depressant [35], narcotic [36], hypotensive, analgesic [37]. Several works have been reported for the synthesis of other spiro barbiturates [38][39][40][41][42][43][44].…”

Section: Introductionmentioning

confidence: 99%

New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures

Pesyan¹,

Noori²,

Poorhassan³

et al. 2014

Bull. Chem. Soc. Eth.

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ABSTRACT. Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.1]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1 H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1 H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks.

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Cited by 31 publications

References 10 publications

All‐Carbon [3+3] Oxidative Annulations of 1,3‐Enynes by Rhodium(III)‐Catalyzed CH Functionalization and 1,4‐Migration

All‐Carbon [3+3] Oxidative Annulations of 1,3‐Enynes by Rhodium(III)‐Catalyzed CH Functionalization and 1,4‐Migration

Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase

New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures

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