Synthesis, crystal structure at 219 K and Hirshfeld surface analyses of 1,4,6-trimethylquinoxaline-2,3(1<i>H</i>,4<i>H</i>)-dione monohydrate

Zouitini, A.; Faizi, Md. Serajul Haque; Ouzidan, Y.; Chahdi, Fouad Ouazzani; Marrot, Jérôme; Prim, Damien; Dege, Necmi; Mashrai, Ashraf

doi:10.1107/s2056989020009573

Cited by 2 publications

(2 citation statements)

References 30 publications

(17 reference statements)

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“…Studies on the crystallographic data of compound ( 3 ) show that alkylation took place at the third position [ 32 ]. Additionally, the crystallized form for 3 and 6 is a monoclinic system ( Figure 1 , Tables S1–S3; Supplementary Materials ).…”

Section: Resultsmentioning

confidence: 99%

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

et al. 2023

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5-bromopyridine-2,3-diamine reacted with benzaldehyde to afford the corresponding 6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridine (1). The reaction of the latter compound (1) with a series of halogenated derivatives under conditions of phase transfer catalysis solid–liquid (CTP) allows the isolation of the expected regioisomers compounds (2–8). The alkylation reaction of (1) gives, each time, two regioisomers, N3 and N4; in the case of ethyl bromoactate, the reaction gives, at the same time, the three N1, N3 and N4 regioisomers. The structures of synthesized compounds were elucidated on the basis of different spectral data (1H NMR, 13C NMR), X-Ray diffraction and theoretical study using the DFT method, and confirmed for each compound. Hirshfeld surface analysis was used to determine the intermolecular interactions responsible for the stabilization of the molecule. Density functional theory was used to optimize the compounds, and the HOMO-LUMO energy gap was calculated, which was used to examine the inter/intra molecular charge transfer. The molecular electrostatic potential map was calculated to investigate the reactive sites that were present in the molecule. In order to determine the potential mode of interactions with DHFR active sites, the three N1, N3 and N4 regioisomers were further subjected to molecular docking study. The results confirmed that these analogs adopted numerous important interactions, with the amino acid of the enzyme being targeted. Thus, the most docking efficient molecules, 2 and 4, were tested in vitro for their antibacterial activity against Gram-positive bacteria (Bacillus cereus) and Gram-negative bacteria (Escherichia coli). Gram-positive bacteria were more sensitive to the action of these compounds compared to the Gram-negative, which were much more resistant.

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Section: Resultsmentioning

confidence: 99%

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

et al. 2023

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“…2): Figure 2 Conventional alkylation techniques which involve weak bases or strong bases have a number of disadvantages: They are expensive, very slow, and lead to the formation of byproducts which are di cult to purify. To circumvent these challenges, we developed another highly e cient alkylation method: phase transfer catalysis (PTC) using K 2 CO 3 as the base and t-BAB as the catalyst [32][33]. We continued our experiments in applying this method for the preparation and study of the antimicrobial activity 1,3,4triazaindan derivatives.…”

Section: Chemistrymentioning

confidence: 99%

New 1,3,4-Triaza-3H-indene Derivatives in Theoretical, Experimental and biological Studies

Ouzidan,

Hjouji,

Hafez

et al. 2024

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6-Bromo-2-phenyl-1,3,4-triazaindan under solid-liquid catalysis-transfer-phase(CTP) environment, pyridine interacts with a number of halogenated derivatives to produce the anticipated regioisomer molecules 2a and 2b. Besides, the reaction of compound (1) with bis(2-chloroethyl) amine results in the corresponding isoxazolidin-2-one derivatives (3a) and (3b) at a satisfactory yield. The synthesized compounds are confirmed by X-ray diffraction, spectral techniques (1H NMR, 13C NMR). Then, 1,3,4-Triaza-3H-indene derivatives were analyzed in silico based on molecular structure by molecular docking analysis to determine which one could be used for in vitro antibacterial activity testing. The compounds with the highest binding efficiency in the docking experiment were chosen to be evaluated against both Gram-positive and Gram-negative bacteria. These compounds showed higher efficacy against Gram-positive bacteria than Gram-negative bacteria, which are much more resistant to them.

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Synthesis, crystal structure at 219 K and Hirshfeld surface analyses of 1,4,6-trimethylquinoxaline-2,3(1H,4H)-dione monohydrate

Cited by 2 publications

References 30 publications

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

New 1,3,4-Triaza-3H-indene Derivatives in Theoretical, Experimental and biological Studies

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