Molecular conformational analysis, vibrational spectra, NBO, NLO, HOMO–LUMO and molecular docking studies of ethyl 3-(E)-(anthracen-9-yl)prop-2-enoate based on density functional theory calculations

Mary, Y. Sheena; Varghese, Hema Tresa; Panicker, C. Yohannan; Thiemann, Thies; Al‐Saadi, Abdulaziz A.; Popoola, Saheed A.; Alsenoy, C. Van; Jasem, Yosef Al

doi:10.1016/j.saa.2015.05.092

Cited by 47 publications

(11 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These values were obtained from zero-point corrected electronic energies for the fully optimized configurations of the three set of bipyridine derivatives. The results obtained for hydroxo derivatives of bipyridine as listed in Table 2, affirms the orthosubstituted configurations as the most stable, followed by the para (1.99 kcal/mol), while the meta counterpart (4.62 kcal/mol) was the least stable conformer [39][40][41]. The stability of ortho configuration over para and meta could be attributed to the electron donating ability of -OH species, which in principle shows activating effect in the order of ortho > para > meta.…”

Section: Stabilitysupporting

confidence: 53%

DFT evaluation of the effects of OH, NH₂ and Br substituents on the properties of 2,2′-bipyridine derivatives

Popoola

Al-Harbi

Al-Rashidi

et al. 2020

Journal of Taibah University for Science

Self Cite

View full text Add to dashboard Cite

A theoretical assessment of the effects of the OH, NH 2 and Br substituents on the properties of 2,2-bipyridine has been carried out using density functional theory approach. The substituents were found to alter both electronic and structural properties of substituted 2,2-bipyridine with the inductive and resonance effects playing significant roles. For the relative stability study, an order of ortho > para > meta was predicted for each set of the 2,2-bipyridine derivatives with the ortho conformers being more stable by 4.62, 6.54 and 2.18 kcal/mol than the meta counterparts of the hydroxo, amino and bromo configurations respectively. On the part of electronic property, the electron donating / withdrawing tendency of the substituents was crucial in making electrons available to the bipyridine system. A general reduction in HOMO-LUMO energy gap was noticed upon substitution with the NH 2 substituent having greater effect. Furthermore, the calculated reactivity parameters of the 2,2-bipyridine were altered by substitution with-OH and-NH 2 substituents causing reduction in ionization potential (IP) and absolute electronegativity (χ) while the-Br substituent did otherwise. For the solubility simulation, a more negative G solution was predicted for the hydroxo and amino derivatives at the para position, but reverse was the case for the bromo counterpart. In the case of the optical property, the range separated Time-dependent (LC-TDDFT) calculation revealed that the shifts in absorption λ max caused by the substitution is both substituent and position dependent.

show abstract

Section: Stabilitysupporting

confidence: 53%

DFT evaluation of the effects of OH, NH₂ and Br substituents on the properties of 2,2′-bipyridine derivatives

Popoola

Al-Harbi

Al-Rashidi

et al. 2020

Journal of Taibah University for Science

Self Cite

View full text Add to dashboard Cite

show abstract

“…The band gap between HOMO and LUMO is around 4.35 eV which represents eventual charge transfer of electrons in the molecule. HOMO and LUMO energy values are also used to find electronegativity, global chemical reactivity descriptors as hardness, chemical potential, and electrophilicity index [23]. To understand the various concepts of pharmacological characteristic of the molecule, several chemical reactivity descriptors are computed by using HOMO and LUMO energies, the ionization energy and electron affinity can be I = −E HOMO = 6.23 eV and A = −E LUMO = 1.88 eV [24].…”

Section: Frontier Molecular Orbital Analysismentioning

confidence: 99%

Conformational Stability, TGA, and Molecular Docking Investigations of p-Coumaric Acid with Special Relevance to Anti-Cancer and Antibacterial Activity

et al. 2017

View full text Add to dashboard Cite

In this work an attempt is made to analysis of the possible different conformers of p-coumaric acid (PCA) by using density functional method. The total energy of four possible conformers were calculated by using B3LYP/6-311G(d,p) method. Computational result identifies that the most stable conformer of PCA is C2. The formation of inter-and intra-molecular hydrogen bonding between -OH and -COOH group gave the evidence for dimer formation for PCA molecule. The highest occupied-lowest unoccupied molecular orbital analysis shows that the negative electrostatic region situated over the -COOH group and positive electrostatic potential region are localized on ring system and all hydrogen. The PCA has been screened to anti-microbial activity and found to exhibit antibacterial effects. Molecular docking results suggest that PCA may exhibit inhibitory activity against lung cancer protein and may act as potential against lung cancer.

show abstract

“…It has been observed in Fig. 6 that the three molecules have very close values for ξHOMO and also for ξLUMO so they have a very close reactivity, that expresses the proximity of the pharmacological effect (Mary et al, 2015) of these molecules towards the receptor site.…”

Section: Resultsmentioning

confidence: 86%

The Development of New Molecules Having Antiemetic Activity Using Molecular Modeling

Kanouni¹,

Benguerba²

2019

Current Research in Bioinformatics

View full text Add to dashboard Cite

The solubility of a drug in water or in the blood represents the most desired parameter in medicine. Our aim is to obtain molecules with properties more effective than those of metoclopramide. In this work, two molecules with high solubility are constructed. Metoclopramide (a benzamide derivative) is a dopamine receptor antagonist used as an antiemetic drug. Its solubility in water is 200 mg/L at 25°C. In this work, we will develop two other molecules that have the same therapeutic activity of metoclopramide with a higher solubility in water, therefore in the blood, without affecting the other properties. The two molecules developed by molecular modeling with a chemical modification of the OH group of metoclopramide have a high solubility: approximately 3 times and 8 times that of metoclopramide. For the other physicochemical properties, there is a great similarity between the molecules. Thus, the two proposed molecules will have antiemetic activity, the second molecule will be more favorable because of its higher solubility and the number of HBA and HBD.

show abstract

Molecular conformational analysis, vibrational spectra, NBO, NLO, HOMO–LUMO and molecular docking studies of ethyl 3-(E)-(anthracen-9-yl)prop-2-enoate based on density functional theory calculations

Cited by 47 publications

References 50 publications

DFT evaluation of the effects of OH, NH₂ and Br substituents on the properties of 2,2′-bipyridine derivatives

DFT evaluation of the effects of OH, NH₂ and Br substituents on the properties of 2,2′-bipyridine derivatives

Conformational Stability, TGA, and Molecular Docking Investigations of p-Coumaric Acid with Special Relevance to Anti-Cancer and Antibacterial Activity

The Development of New Molecules Having Antiemetic Activity Using Molecular Modeling

Contact Info

Product

Resources

About

Molecular conformational analysis, vibrational spectra, NBO, NLO, HOMO–LUMO and molecular docking studies of ethyl 3-(E)-(anthracen-9-yl)prop-2-enoate based on density functional theory calculations

Cited by 47 publications

References 50 publications

DFT evaluation of the effects of OH, NH2 and Br substituents on the properties of 2,2′-bipyridine derivatives

DFT evaluation of the effects of OH, NH2 and Br substituents on the properties of 2,2′-bipyridine derivatives

Conformational Stability, TGA, and Molecular Docking Investigations of p-Coumaric Acid with Special Relevance to Anti-Cancer and Antibacterial Activity

The Development of New Molecules Having Antiemetic Activity Using Molecular Modeling

Contact Info

Product

Resources

About

DFT evaluation of the effects of OH, NH₂ and Br substituents on the properties of 2,2′-bipyridine derivatives

DFT evaluation of the effects of OH, NH₂ and Br substituents on the properties of 2,2′-bipyridine derivatives