Synthesis, Crystal Structure, Hirshfeld Surface Analysis, Molecular Docking, IR Spectroscopy and DFT Calculations of a Novel 2D Layered Hybrid Compound (C6H10N3O)2Cu2Cl6

Gharbi, Chaima; Sert, Yusuf; Çınar, Emine Berrin; Böhme, Uwe; Dege, Necmi; Nasr, C. Ben; Khedhiri, Lamia

doi:10.1007/s10876-022-02314-6

Cited by 4 publications

(3 citation statements)

References 51 publications

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“…The SwissADME provides a BOILED-Egg method, which is considered an accurate predictive model for both brain and intestinal permeation. The BOILED-Egg consists of two regions: the white region is the physiochemical space of molecules with the highest probability of being absorbed by the gastrointestinal tract, and the yellow region is the physiochemical space of molecules with the highest probability of permeating to the brain (Gharbi et al, 2023). From the above results, it is confirmed that both I and II have good pharmacokinetic and druglikeness properties.…”

Section: In-silico Adme Predictionmentioning

confidence: 66%

Synthesis and structural investigation of salts of 2-amino-3-methylpyridine with carboxylic acid derivatives: an experimental and theoretical study

Balasubramanian,

Ashraf,

Karuppannan

et al. 2024

Acta Crystallogr C

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The salts bis(2-amino-3-methylpyridinium) fumarate dihydrate, 2C6H9N2 +·C4H2O2 2−·2H2O (I), and 2-amino-3-methylpyridinium 5-chlorosalicylate, C6H9N2 +·C7H4ClO3 − (II), were synthesized from 2-amino-3-methylpyridine with fumaric acid and 5-chlorosalicylic acid, respectively. The crystal structures of these salts were characterized by single-crystal X-ray diffraction, revealing protonation in I and II by the transfer of a H atom from the acid to the pyridine base. In the crystals of both I and II, N—H...O interactions form an R 2 2(8) ring motif. Hirshfeld surface analysis distinguishes the interactions present in the crystal structures of I and II, and the two-dimensional (2D) fingerprint plot analysis shows the percentage contribution of each type of interaction in the crystal packing. The volumes of the crystal voids of I (39.65 Å3) and II (118.10 Å3) have been calculated and reveal that the crystal of I is more mechanically stable than II. Frontier molecular orbital (FMO) analysis predicts that the band gap energy of II (2.6577 eV) is lower compared to I (4.0035 eV). The Quantum Theory of Atoms In Molecules (QTAIM) analysis shows that the pyridinium–carboxylate N—H...O interaction present in I is stronger than the other interactions, whereas in II, the hydroxy–carboxylate O—H...O interaction is stronger than the pyridinium–carboxylate N—H...O interaction; the bond dissociation energies also confirm these results. The positive Laplacian [∇2ρ(r) > 0] of these interactions shows that the interactions are of the closed shell type. An in-silico ADME (Absorption, Distribution, Metabolism and Excretion) study predicts that both salts will exhibit good pharmacokinetic properties and druglikeness.

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Section: In-silico Adme Predictionmentioning

confidence: 66%

Synthesis and structural investigation of salts of 2-amino-3-methylpyridine with carboxylic acid derivatives: an experimental and theoretical study

Balasubramanian,

Ashraf,

Karuppannan

et al. 2024

Acta Crystallogr C

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“…According to the Pfizer rule, a potential drug candidate should exhibit two or more of the Lipinski conditions (Gharbi et al, 2023). SwissADME (http://www.swissadme.ch/) was used to predict the ADME property of both salts (Daina et al, 2017).…”

Section: Adme Predictionmentioning

confidence: 99%

“…9) in the brain and gastrointestinal tract (Daina & Zoete, 2016). According to the BOILED-Egg diagram of salts I and II, I is located in the yellow yolk region, which represents the physiochemical space of molecules with the highest probability of permeating to the brain (Gharbi et al, 2023). Salt II is located in the white region, which indicates that the molecule has the highest probability of being absorbed by the gastrointestinal (GI) tract.…”

Section: Adme Predictionmentioning

confidence: 99%

Crystal structure, intermolecular interactions, charge–density distribution and ADME properties of the acridinium 4-nitrobenzoate and 2-amino-3-methylpyridinium 4-nitrobenzoate salts: a combined experimental and theoretical study

Balasubramanian,

Mariappan,

Poomani

2024

Acta Crystallogr C

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Acridines are a class of bioactive agents which exhibit high biological stability and the ability to intercalate with DNA; they have a wide range of applications. Pyridine derivatives have a wide range of biological activities. To enhance the properties of acridine and 2-amino-3-methylpyridine as the active pharmaceutical ingredient (API), 4-nitrobenzoic acid was chosen as a coformer. In the present study, a mixture of acridine and 4-nitrobenzoic acid forms the salt acridinium 4-nitrobenzoate, C13H10N+·C7H4NO4 − (I), whereas a mixture of 2-amino-3-methylpyridine and 4-nitrobenzoic acid forms the salt 2-amino-3-methylpyridinium 4-nitrobenzoate, C6H9N2 +·C7H4NO4 − (II). In both salts, protonation takes place at the ring N atom. The crystal structure of both salts is predominantly governed by hydrogen-bond interactions. In salt I, C—H...O and N—H...O interactions form an infinite chain in the crystal, whereas in salt II, intermolecular N—H...O interactions form an eight-membered R 2 2(8) ring motif. A theoretical charge–density analysis reveals the charge–density distribution of the inter- and intramolecular interactions of both salts. An in-silico ADME analysis predicts the druglikeness properties of both salts and the results confirm that both salts are potential drug candidates with good bioavailability scores and there is no violation of the Lipinski rules, which supports the druglikeness properties of both salts. However, although both salts exhibit drug-like properties, salt I has higher gastrointestinal absorption than salt II and hence it may be considered a potential drug candidate.

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Crystal structure, intermolecular interactions, charge density distribution and ADME properties of 2-Amino-4-methylpyridinium (oxalate) 0.5: An experimental and theoretical study

Hemalatha,

Suresh,

Poomani

2023

Chemical Data Collections

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Synthesis, Crystal Structure, Hirshfeld Surface Analysis, Molecular Docking, IR Spectroscopy and DFT Calculations of a Novel 2D Layered Hybrid Compound (C6H10N3O)2Cu2Cl6

Cited by 4 publications

References 51 publications

Synthesis and structural investigation of salts of 2-amino-3-methylpyridine with carboxylic acid derivatives: an experimental and theoretical study

Synthesis and structural investigation of salts of 2-amino-3-methylpyridine with carboxylic acid derivatives: an experimental and theoretical study

Crystal structure, intermolecular interactions, charge–density distribution and ADME properties of the acridinium 4-nitrobenzoate and 2-amino-3-methylpyridinium 4-nitrobenzoate salts: a combined experimental and theoretical study

Crystal structure, intermolecular interactions, charge density distribution and ADME properties of 2-Amino-4-methylpyridinium (oxalate) 0.5: An experimental and theoretical study

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