A comparative study of cooperative effects between the intramolecular hydrogen bond and cation···π interaction in various complexes of ortho-aminobenzaldehyde with its thio and seleno analogous

Nowroozi, Alireza; Rad, Omid Rezvani

doi:10.1007/s00214-016-2047-x

Cited by 8 publications

(4 citation statements)

References 42 publications

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“…Moreover, MD simulation plays a critical role in assessing theoretical accuracy, necessitating significant computational resources. Various theoretical methods are employed during MD analysis to select conformations from simulations, enabling the identification of relevant molecular conformations and aiding in the interpretation of simulation data [ 35 , 36 ]. To evaluate the stability of the binding poses and assess the dynamics of the protein conformation, molecular dynamics (MD) simulations were conducted for 100 ns on protein–ligand complexes involving compounds 8a , 8h , and 8i .…”

Section: Resultsmentioning

confidence: 99%

Integration of Hybridization Strategies in Pyridine–Urea Scaffolds for Novel Anticancer Agents: Design, Synthesis, and Mechanistic Insights

et al. 2023

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Annually, millions of new cancer cases are reported, leading to millions of deaths worldwide. Among the newly reported cases, breast and colon cancers prevail as the most frequently detected variations. To effectively counteract this rapid increase, the development of innovative therapies is crucial. Small molecules possessing pyridine and urea moieties have been reported in many of the currently available anticancer agents, especially VEGFR2 inhibitors. With this in mind, a rational design approach was employed to create hybrid small molecules combining urea and pyridine. These synthesized compounds underwent in vitro testing against breast and colon cancer cell lines, revealing potent submicromolar anticancer activity. Compound 8a, specifically, exhibited an impressive GI50 value of 0.06 μM against the MCF7 cancer cell line, while compound 8h displayed the highest cytotoxic activity against the HCT116 cell line, with a GI50 of 0.33 ± 0.042 μM. Notably, compounds 8a, 8h, and 8i demonstrated excellent safety profiles when tested on normal cells. Molecular docking, dynamic studies, and free energy calculations were employed to validate the affinity of these compounds as VEGFR2 inhibitors.

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Section: Resultsmentioning

confidence: 99%

Integration of Hybridization Strategies in Pyridine–Urea Scaffolds for Novel Anticancer Agents: Design, Synthesis, and Mechanistic Insights

et al. 2023

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“…In general, aromatic compounds have high thermodynamic stability and are substantially more stable than antiaromatic compounds. Although aromaticity cannot be directly measured experimentally, various parameters based on geometric ( Listunov et al, 2018 ), thermodynamics ( Nowroozi1 and Rad, 2017 ; Rakhi and Suresh, 2016 ), magnetic ( Najmidin et al, 2013 ; Torrent-Sucarrat et al, 2017 ), and electronic properties can be used to evaluate aromaticity and antiaromaticity of molecules. In particular, the nucleus-independent chemical shift (NICS) analysis is the most popular method for determining the aromaticity of molecules due to its simplicity and effectivity ( Schleyer et al, 1996 ).…”

Section: Introductionmentioning

confidence: 99%

Theoretical analysis of expanded porphyrins: Aromaticity, stability, and optoelectronic properties

et al. 2022

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Expanded porphyrin systems are capable of binding a variety of substrates due to their increased cavity size and aromatic nature, holding important applications as magnetic resonance imaging contrast agents and as sensitizers for photodynamic therapy. It is there of fundamental interest to know the photoelectrical properties of expanded porphyrins using quantum chemistry calculations. In this work, we theoretically designed and screened a series of expanded porphyrins by incorporating terthiophene (TTH) and dithienothiophene (DTT) moieties. Our calculations showed that all the designed molecules exhibit excellent optoelectronic performance than the reference molecule. It is suggested that the porphyrin molecule with TTH moiety has better stability than the one with DTT moiety. Finally, we demonstrated that molecule 2 features with TTH moiety and the inverted selenophene ring outperform other molecules because it exhibits increased HOMO-LUMO gap, planar geometry, and strengthened aromaticity. We expect that this work can provide theoretical guidelines for the design of novel porphyrin materials.

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“…In 2017, Nowroozi et al [22] investigated interplay between the IMHB and cation-π interactions in the various complexes of salicylaldehyde, thiosalicylaldehyde and selenosalicylaldehyde with Li + , Na + , K + , Mg 2+ and Ca 2+ cations. Also, a comparative study of the cooperative effects between the cation-π and IMHB interactions in the various complexes of ortho-aminobenzaldehyde with its thio and seleno analogous analyzed in 2017 [23].…”

Section: Introductionmentioning

confidence: 99%

Exploration of the Mutual Effects Between Cation–π and Intramolecular Hydrogen Bond Interactions in the Different Complexes of Mesalazine with Metal Cations of Alkali and Alkaline-Earth: A DFT Study

Mohammadi¹,

Alirezapour²,

Khanmohammadi³

2021

Preprint

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In the current research, a comparative study of the interplay effects between cation–π and intramolecular hydrogen bond (IMHB) interactions is performed on the complexes of mesalazine with Li+, Na+, K+, Be2+, Mg2+ and Ca2+ cations using density functional theory (DFT). For this purpose, the mesalazine analogue and the equivalent values of 3-aminobenzoic acid complexes with the cited cations are selected as a set of reference points. In order to understand the mutual effects between these interactions, the descriptors of geometrical, binding energies, topological properties and charge transfer values are examined on complexes using the atoms in molecules (AIM) and natural bond orbital (NBO) analyses. Results indicate that with the exception of Be2+ complex, the coupling simultaneously weakens both of the interactions. Finally, the physical properties such as energy gap, chemical hardness as well as electronic chemical potential of complexes are systematically analyzed by using frontier molecular orbitals.

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A comparative study of cooperative effects between the intramolecular hydrogen bond and cation···π interaction in various complexes of ortho-aminobenzaldehyde with its thio and seleno analogous

Cited by 8 publications

References 42 publications

Integration of Hybridization Strategies in Pyridine–Urea Scaffolds for Novel Anticancer Agents: Design, Synthesis, and Mechanistic Insights

Integration of Hybridization Strategies in Pyridine–Urea Scaffolds for Novel Anticancer Agents: Design, Synthesis, and Mechanistic Insights

Theoretical analysis of expanded porphyrins: Aromaticity, stability, and optoelectronic properties

Exploration of the Mutual Effects Between Cation–π and Intramolecular Hydrogen Bond Interactions in the Different Complexes of Mesalazine with Metal Cations of Alkali and Alkaline-Earth: A DFT Study

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