Intramolecular H-bonding interaction in angular 3-π-EWG substituted imidazo[1,2-a]pyridines contributes to conformational preference

Velázquez-Ponce, Manuel; Salgado-Zamora, Héctor; Jiménez‐Vázquez, Hugo A.; Campos-Aldrete, Ma. Elena; Jiménez, Rogelio; Cervantes, Humberto; Hadda, Taïbi Ben

doi:10.1186/1752-153x-7-20

Cited by 5 publications

(4 citation statements)

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“…The interaction energies of polar hydrogen-π interactions are much stronger than that of nonpolar hydrogen-π interactions (CH-π), comparable or even larger than common hydrogen bonds. In this study the notation Hp-π is used for the polar hydrogen-π interactions, to make difference from the nonpolar hydrogen-π interactions (H-π or CH-π), and the common hydrogen bond interactions (H-b) [21-25]. …”

Section: Introductionmentioning

confidence: 99%

“…The Hp-π interactions are a unique interaction type that cannot be classified into other molecular interaction types, such as common hydrogen bond [21-25], cation-π interaction [26-29], electrostatic interaction, and van der Waals interaction. The physical nature and the interaction strength of Hp-π interactions are often a debatable topic.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical study on the polar hydrogen-π (Hp-π) interactions between protein side chains

Wang

et al. 2013

Chemistry Central Journal

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BackgroundIn the study of biomolecular structures and interactions the polar hydrogen-π bonds (Hp-π) are an extensive molecular interaction type. In proteins 11 of 20 natural amino acids and in DNA (or RNA) all four nucleic acids are involved in this type interaction.ResultsThe Hp-π in proteins are studied using high level QM method CCSD/6-311 + G(d,p) + H-Bq (ghost hydrogen basis functions) in vacuum and in solutions (water, acetonitrile, and cyclohexane). Three quantum chemical methods (B3LYP, CCSD, and CCSD(T)) and three basis sets (6-311 + G(d,p), TZVP, and cc-pVTZ) are compared. The Hp-π donors include R2NH, RNH2, ROH, and C6H5OH; and the acceptors are aromatic amino acids, peptide bond unit, and small conjugate π-groups. The Hp-π interaction energies of four amino acid pairs (Ser-Phe, Lys-Phe, His-Phe, and Tyr-Phe) are quantitatively calculated.ConclusionsFive conclusion points are abstracted from the calculation results. (1) The common DFT method B3LYP fails in describing the Hp-π interactions. On the other hand, CCSD/6-311 + G(d,p) plus ghost atom H-Bq can yield better results, very close to the state-of-the-art method CCSD(T)/cc-pVTZ. (2) The Hp-π interactions are point to π-plane interactions, possessing much more interaction conformations and broader energy range than other interaction types, such as common hydrogen bond and electrostatic interactions. (3) In proteins the Hp-π interaction energies are in the range 10 to 30 kJ/mol, comparable or even larger than common hydrogen bond interactions. (4) The bond length of Hp-π interactions are in the region from 2.30 to 3.00 Å at the perpendicular direction to the π-plane, much longer than the common hydrogen bonds (~1.9 Å). (5) Like common hydrogen bond interactions, the Hp-π interactions are less affected by solvation effects.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theoretical study on the polar hydrogen-π (Hp-π) interactions between protein side chains

Wang

et al. 2013

Chemistry Central Journal

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“…44 65.07 2g 63.17HURZOL 45 65.16RELQUW 46 64.98 2h 64.74KABMIM 47 66.21RUJNEQ. 48 64.61 2i 63.81MIXZOJ 49 65.44TIDVIN 50 66.07 2j 64.63MIXZUP 51 67.52TUZYEU 52 65.44 2k 65.36MONREO 53 66.12UTITEX 54 62.07 2l 67.34NAGGEH 55 65.27VEGKAU 56 64.34 2m 60.69NAGGEH01 57 64.84WUHKER 58 62.24 2n 62.87NOGRIM 59 65.44YEDHIY 60 63.06 2o 66.69NONFOM 61 64.30ZUNVOV 62 68.57AHOMIV 63 63.75NONFOM01 61 65.95ZUPCOE 62 66.04BEGTUE 64 62.92NUBVUD 65 63.87ZUSSAJ 66 63.31CAJTIQ 67 67.82NUBWAK 65 64.00…”

Section: Resultsmentioning

confidence: 99%

Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation

Kwong

Kumar

Mah

et al. 2019

Sci Rep

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Imidazo[1,2-a]pyridine-based compounds are clinically important to the treatments of heart and circulatory failures, while many are under development for pharmaceutical uses. In this study, a series of imidazo[1,2-a]pyridine-based derivatives 2(a–o) were synthesized by reacting a-haloketones with 2-aminopyridines in a basic media at ambient temperature. Single crystal X-ray diffraction studies suggest that with low degree-of-freedom, the introduction of bulky adamantyl or electron-rich biphenyl moiety into the imidazopyridine derivatives will not affect its structural occupancy. Imidazo[1,2-a]pyridine-based derivatives with biphenyl side chain are potential AChE inhibitors. Compound 2h which bears a biphenyl side chain and methyl substituent at the position R4 of the imidazo[1,2-a]pyridine ring showed the strongest AChE inhibition with an IC50 value of 79 µM. However, imidazo[1,2-a]pyridine derivatives with phenyl side chain exhibit better BChE inhibition effect among the series. Compound 2j with 3,4-dichlorophenyl side chain and unsubstituted imidazo[1,2-a]pyridine ring appears to be the strongest BChE inhibitor with an IC50 value of 65 µM and good selectivity. The inhibitory effects of active compounds were further confirmed by computational molecular docking studies. The results unveiled that peripheral anionic sites of AChE and acyl pocket of BChE were the predominated binding sites for the subjected inhibitors.

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“…To exclude a misleading crystal packing effect, we carried out a quantum chemical modeling of both conformations of the rac -Ir5-TfO cation in the absence of crystal effects at the PBE0-D3/IMCP-SR1 , //PBE0-D3/SBKJC SMD(butanol) level of theory (full computational details in SI). These calculations revealed that conformer A is indeed 5.3 kcal·mol –1 lower in energy than B, which affirms that conformer A is clearly preferred in solution as well . Having ruled out excessive conformational freedom of the N -bound acyl group, we were now able to shed light on the underlying manner of chiral recognition of intermediates of type Λ-Ir5-Int by the addition of a molecular surface to the complex cation of intermediate analog Λ-Ir5-TfO (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Nucleophilic Catalysis with an Octahedral Chiral-at-Metal Iridium(III) Complex

et al. 2017

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Herein, we report about the design, synthesis, and application of a nucleophilic octahedral chiral-only-at-metal iridium(III) complex. We demonstrate that the enantiopure form of this complex serves as an efficient catalyst for the asymmetric Steglich rearrangement of O-acylated azlactones (up to 96% ee and 99% yield) and the related asymmetric Black rearrangement of O-acylated benzofuranones (up to 94% ee and 99% yield). We provide insight into the mechanisms of these two acyl migration reactions and the catalyst’s manner of chiral recognition with crystal structures of the active catalyst and a catalysis intermediate analog, as well as with quantum chemical calculations based on them. Furthermore, we demonstrate that the presented catalyst also efficiently catalyzes the asymmetric reaction between aryl alkyl ketenes and 2-cyanopyrrole to give the corresponding α-chiral N-acyl pyrroles (up to 95% ee and 99% yield).

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Intramolecular H-bonding interaction in angular 3-π-EWG substituted imidazo[1,2-a]pyridines contributes to conformational preference

Cited by 5 publications

References 28 publications

Theoretical study on the polar hydrogen-π (Hp-π) interactions between protein side chains

Theoretical study on the polar hydrogen-π (Hp-π) interactions between protein side chains

Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation

Asymmetric Nucleophilic Catalysis with an Octahedral Chiral-at-Metal Iridium(III) Complex

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