Synthesis, crystal structure, Hirshfeld surface analysis, spectral characterizations and quantum computational assessments of 1‑hydroxy-3-methyl-11H-pyrido[2,1-b] quinazolin-11-one

Lahmidi, Sanae; Sert, Yusuf; Şen, Fatih; Hafi, Mohamed El; Ettahiri, Walid; Gökçe, Halil; Essassi, El Mokhtar; Mague, Joel T.; Ucun, Fatih

doi:10.1016/j.molstruc.2021.131592

Cited by 8 publications

(4 citation statements)

References 53 publications

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“…The retro-Claisen reaction, a useful synthetic tool in organic chemistry, leads to carboxylic acid derivatives involving a β-dicarbonyl carbon-carbon bond cleavage under various conditions [17,18]. Continuing our previous investigations on the synthesis of pyrido [1,2-a]pyrimidine derivatives [19,20], we describe the alkaline cleavage of 1-(4-oxo-4Hpyrido[1,2-a]pyrimidin-3-yl)butane-1,3-dione (3), which acts as an unsymmetrical βdiketone. This cleavage was carried out using potassium hydroxide and 4-dimethylaminopyridine as bases under refluxing conditions in ethanol.…”

Section: Mechanism Of the Synthesis Of 4-(dimethylamino)pyridin-1-ium...mentioning

confidence: 74%

Nanoarchitectonics and Molecular Docking of 4-(Dimethylamino)Pyridin-1-Ium 2-3 Methyl-4-Oxo-Pyri-Do[1,2-a]Pyrimidine-3-Carboxylate

Lahmidi,

Anouar,

Ettahiri

et al. 2023

Crystals

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A retro-Claisen reaction of 1-(4-oxo-4H-pyrido [1,2-a]pyrimidin-3-yl)butane-1,3-dione, 3, in the presence of potassium hydroxide and 4-dimethylamino-pyridine has been carried out, leading to 4-(dimethylamino)pyridin-1-ium 2-methyl-4-oxo-pyrido [1,2-a]pyrimidine-3-carboxylate 5. A plausible mechanism explaining the formation of the title compound has been proposed. A single-crystal X-ray diffraction analysis confirms the crystal structure of the isolated organic salt (5). In the crystal, the title compound adopts a layered structure where there are stacks of cations and anions formed by slipped π-stacking interactions. These stacks are linked by regions consisting of water molecules that are hydrogen-bonded together. DFT and Hirshfeld surface analysis supported the experimental results of the molecular geometry and the intercontacts between different units in the crystal. The druglikeness, ADMET properties, and predicted targets were investigated, and the observed results suggest that 5 may act as a carbonic anhydrase I inhibitor. The assumption is confirmed by docking 5 into the active binding site of carbonic anhydrase, which shows it to have good binding affinities and to form stable complexes with the active residues of carbonic anhydrase I.

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Section: Mechanism Of the Synthesis Of 4-(dimethylamino)pyridin-1-ium...mentioning

confidence: 74%

Nanoarchitectonics and Molecular Docking of 4-(Dimethylamino)Pyridin-1-Ium 2-3 Methyl-4-Oxo-Pyri-Do[1,2-a]Pyrimidine-3-Carboxylate

Lahmidi,

Anouar,

Ettahiri

et al. 2023

Crystals

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“…[ 20 ] We have also showed that the heterocyclic β‐diketone 4 has been condensed with a variety of nucleophilic reagents to give new heterocyclic systems containing pyridopyridine, pyrazole, isoxazole, hydroxyl‐quinazoline moieties. [ 21–24 ]…”

Section: Resultsmentioning

confidence: 99%

“…[20] We have also showed that the heterocyclic β-diketone 4 has been condensed with a variety of nucleophilic reagents to give new heterocyclic systems containing pyridopyridine, pyrazole, isoxazole, hydroxyl-quinazoline moieties. [21][22][23][24] In continuation of our research work in this area, we studied the condensation of compound 4 with 5-amino-3-cyano-4-methyl-pyrazole 1 in refluxing ethanol for 24 hr. The reaction leads to the formation of the unexpected bipyrazolopyrimidine 3 next to pyridopyrimidinone 6 which were separated by silica gel column chromatography to afford 45% of compound 3 and 8% of 6 (Scheme 2).…”

Section: Plausible Mechanism Of the Synthesis Ofmentioning

confidence: 99%

A new synthetic route for the preparation of 2,2′,5′‐trimethyl‐7‐oxo‐4,7‐dihydro‐[6,7′‐bipyrazolo[1,5‐a]pyrimidine]‐3,3′‐dicarbonitrile, structural elucidation, Hirshfeld surface analysis, energy framework, density functional theory and molecular docking investigations

Hafi

Lahmidi

Boulhaoua

et al. 2022

J Chinese Chemical Soc

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A new bipyrazolo [1,5‐a]pyrimidine derivative, 2,2′,5′‐trimethyl‐7‐oxo‐4,7‐dihydro‐[6,7′‐bipyrazolo[1,5‐a]pyrimidine]‐3,3′‐dicarbonitrile dihydrate acetic acid solvate (3) has been synthesized via two different methods and characterized by single‐crystal X‐ray diffraction (XRD) and spectroscopic techniques. A plausible reaction mechanism in the synthesis of 3 through the two synthetic routes used has been proposed. The XRD analysis reveals that the two bicyclic moieties in 3 are close to perpendicular to one another. Some formal double bonds appear localized while others appear to involve some delocalization. In the crystal structure, a layer structure is formed by OH⋯O, OH⋯N and NH⋯O hydrogen bonds, along with weak CH⋯O and π‐stacking interactions. The energy framework indicates that the packing of 3 is mainly determined by dispersion interactions between molecules. The frontier molecular orbital analysis shows that 3 may act more as a nucleophile than an electrophile. The analysis of the Hirshfeld surface maps and 2D fingerprint plots of 3 reveal that intermolecular hydrogen bonding and H⋯H, N⋯H and O⋯H contacts are the major ones between the units of 3. The antibacterial activity of 3 is explored by its molecular docking into the binding site of tyrosyl‐tRNA synthetase, where it formed a stable complex with the amino acids of tyrosyl‐tRNA synthetase mainly through hydrogen bonding.

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“…Nanotechnology, which deals with such small-sized particles, therefore enters almost every eld of human science [31]. The main ones are elds such as sensors [32][33][34][35][36], energy studies [37][38][39], photocatalysis [40,41], chemistry [42,43], biology [44,45], medicine [32,46], optics [47] electronics [48,49], etc. In photocatalytic reactions, UV light acts as a photocatalyst.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and photocatalytic activation of zinc nanoparticles via biogenic methods

ALTUNER

2024

Preprint

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In this study, zinc nanoparticles (Zn NPs) were synthesized from the leaves of the plant Hypericum calycinum L by the biogenic method. Ultra-violet visible spectrum (UV-Vis), Fourier transmission electron spectroscopy (FTIR), transmission electron microscopy (TEM), and X-Ray were used to examine the absorbance, vibration bands, morphological structure, particle size, and crystalline size of the synthesized Zn NPs, respectively. Diffraction characterization (XRD) was performed. According to the results obtained, it was calculated that NPs gave peaks in the absorbance ranges of 274 and 370 nm, had a size of 29.066 ± 10.561 nm, and their crystalline size was 16 nm. Then, photocatalytic processes were started for the removal of methylene blue (MB) dye by combining the catalysis of NPs under the photocatalysis of sunlight. The degradation process provided by photocatalytic processes was carried out every half hour for 150 minutes. As a result of 150 minutes, the photodegradation efficiency was calculated to be 70%. This study supports future photodegradation studies for the removal of waste dyestuffs.

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Synthesis, crystal structure, Hirshfeld surface analysis, spectral characterizations and quantum computational assessments of 1‑hydroxy-3-methyl-11H-pyrido[2,1-b] quinazolin-11-one

Cited by 8 publications

References 53 publications

Nanoarchitectonics and Molecular Docking of 4-(Dimethylamino)Pyridin-1-Ium 2-3 Methyl-4-Oxo-Pyri-Do[1,2-a]Pyrimidine-3-Carboxylate

Nanoarchitectonics and Molecular Docking of 4-(Dimethylamino)Pyridin-1-Ium 2-3 Methyl-4-Oxo-Pyri-Do[1,2-a]Pyrimidine-3-Carboxylate

A new synthetic route for the preparation of 2,2′,5′‐trimethyl‐7‐oxo‐4,7‐dihydro‐[6,7′‐bipyrazolo[1,5‐a]pyrimidine]‐3,3′‐dicarbonitrile, structural elucidation, Hirshfeld surface analysis, energy framework, density functional theory and molecular docking investigations

Synthesis, characterization and photocatalytic activation of zinc nanoparticles via biogenic methods

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