New compounds containing 1,2,4triazolo 1,5-apyridine (I), pyrazolo 1,5-apyridine (II), 1H-1,3-benzodiazole (III) and imidazo 1,2-apyrimidine (IV) backbones were designed and synthesized for PDE10A ...interaction. Among these compounds, 1H-1,3-benzodiazoles and imidazo 1,2-apyrimidines showed the highest affinity for PDE10A enzyme as well as good metabolic stability. Both classes of compounds were identified as selective and potent PDE10A enzyme inhibitors.
Display omitted
•New classes of PDE10 inhibitors were designed based on Example 1a by BMS.•Four different heterocyclic cores were explored.•Two obtained lead classes of compounds are selective and metabolically stable.•Compound 66 proved to be equally potent and 10-fold more stable than Example 1a.
Display omitted
•The synthesis of 6H-2,2a1,3-triazaaceanthrylen-6-ones and 6H-2,2a1,4-triazaaceanthrylen-6-ones.•Pd-catalyzed tandem cyclization of imidazo1,2-apyrimidines/imidazo1,2-apyrazines with ...2-chlorobenzaldehydes.•Two operationally simple one-pot protocols in aqueous medium under air.
Two operationally simple one-pot protocols have been developed for the synthesis of 6H-2,2a1,3-triazaaceanthrylen-6-ones and 6H-2,2a1,4-triazaaceanthrylen-6-ones. The first Pd-catalyzed tandem cyclization of imidazo1,2-apyrimidines/imidazo1,2-apyrazines with 2-chlorobenzaldehydes could proceed in aqueous medium under air, affording the desired products in moderate to good yields. The molecular structures of products 3i and 5b were confirmed by X-ray crystallographic analysis.
A facile and efficient method for the synthesis of benzo4,5imidazo1,2-apyrimidines has been achieved via highly active and reusable heterogeneous poly acrylic acid-supported layered double hydroxides ...(PAA-g-LDHs) catalyst promoted one-pot reaction of 1H-benzodimidazol-2-amine, with α,β-unsaturated carbonyl compounds under solvent-free conditions. PAA-g-LDHs catalyst was successfully synthesized via reversible addition-fragmentation chain-transfer polymerization using grafting reaction and was characterized by different analytical techniques. The significant features of this reaction include expedient one-pot process, short reaction time, excellent yields, wide substrate scope and operational simplicity. Also, the catalyst could be reused for several consecutive runs without any apparent loss in its catalytic activity.
Display omitted
A novel series of 2‐coumarin‐3‐yl‐imidazo1,2‐apyrimidines have been synthesized with functionalized coumarin and pyrimidine units of the different architecture to give various fluorescent compounds. ...A new additional series bearing unsubstituted coumarin and 7‐dialkylaminocoumarin as fluorophore were obtained by palladium‐catalyzed cross‐coupling reactions, through coupling of 6‐bromo‐2‐coumarin‐3‐yl‐imidazopyrimidine derivatives with various arylboronic acids. In the all reaction step, microwave irradiation (MWI) method was used and compared with the conventional method (CM). Photophysical properties of synthesized compounds were studied by a combination of UV/Vis and fluorescence spectroscopy in various solvents having different polarities. The protonation abilities of all compounds were investigated by titration with trifluoroacetic acid (TFA) in dichloromethane. In both series, the compounds bearing 7‐dialkylaminocoumarin are fluorescently active even in daylight and showed maximum absorption wavelengths (λabs–max) in the visible region in all solvents used. In addition, they showed drastic color and emission change in acidic environment. Moreover, for the investigation of protonation ability of three selected compounds bearing 7‐dialkylaminocoumarin have been studied using a buffer solution with various pH and determinated their pKa values. The compound bearing morpholine has the potential to use as colorimetric and luminescence pH sensor. The thermal properties of all the synthesized compounds were also evaluated with TGA to test their usability as optic dyes.
The design and synthesis of 2‐coumarin‐3‐yl‐imidazo1,2‐apyrimidine derivatives as novel pH sensitive dyes are described. The photophysical properties and protonation abilities of these dyes were investigated for their using as fluorescent pH chemosensor in aqueous solution.
Display omitted
We report a practical high-yield synthesis of 5,7-disubstituted-1,2,4-triazolo1,5-apyrimidines using a base-assisted cyclocondensation of chalcone and 1,2,4-triazol-3-amine in an open ...reaction vessel. The same conditions can also be used for the preparation of novel imidazo1,2-apyrimidine derivatives.
Summary of main observation and conclusion
A DMAP (2‐dimethylaminopyridine)‐catalyzed condensation reactions for the successful direct construction of pyrimido1,2‐abenzimidazole or ...imidazo1,2‐apyrimidine has been developed. The method utilizes readily available α‐bromocinnamaldehydes with 2‐aminobenzimidazole or 2‐aminoimidazole as starting materials in the presence of 2‐DMAP/TBHP. In the process, two C—N bonds were successfully constructed to synthesize target compounds. The current method features wide substrate scope, product diversification, and metal‐free conditions.
A 2‐dimethylaminopyridine‐catalyzed condensation reactions for the successful direct construction of pyrimido1,2‐abenzimidazole or imidazo1,2‐apyrimidine has been developed. The current method features wide substrate scope, product diversification, and metal‐free conditions.
A series of 3-benzoyl imidazo1,2-
pyrimidines, obtained from
-heteroarylformamidines in good yields, was tested in silico and in vitro for binding and inhibition of seven
species (
(ATCC 10231),
...(CD36),
(CBS138),
(ATCC 6260),
,
(ATCC 6358) and
(MYA-3404)). To predict binding mode and energy, each compound was docked in the active site of the lanosterol 14α-demethylase enzyme (CYP51), essential for fungal growth of
species. Antimycotic activity was evaluated as the 50% minimum inhibitory concentration (MIC50) for the test compounds and two reference drugs, ketoconazole and fluconazole. All test compounds had a better binding energy (range: -6.11 to -9.43 kcal/mol) than that found for the reference drugs (range: 48.93 to -6.16 kcal/mol). In general, the test compounds showed greater inhibitory activity of yeast growth than the reference drugs. Compounds
and
were the most active, indicating an important role in biological activity for the benzene ring with electron-withdrawing substituents. These compounds show the best MIC50 against
C.
respectively. The current findings suggest that the 3-benzoyl imidazo1,2-
pyrimidine derivatives, herein synthesized by an accessible methodology, are potential antifungal drugs.
The review discusses the use of the Dimroth rearrangement in the synthesis of condensed pyrimidines which are key structural fragments of antiviral agents. The main attention is given to publications ...over the past 10 years. The bibliography includes 107 references.
An efficient procedure between imidazo1,2-
a
pyrimidine-2-carbaldehyde, malononitrile, enolizable C–H activated acidic compounds, and sodium carbonate is described for the synthesis of potential ...biologically active, novel imidazo1,2-
a
pyrimidine-based pyran analogs through one pot, multicomponent reactions at room temperature. This method provided mild reaction conditions, simple purification without column chromatography, and moderate to good yields for the construction of imidazo1,2-
a
pyrimidine-based pyran derivatives. The structures of target compounds were established with different spectroscopic analyses.
Graphic abstract
PDF
