DFT and TDDFT investigation of the Schiff base formed by tacrine and saccharin

Açar, Nursel; Selçuki, Cenk; Coşkun, Emine

doi:10.1007/s00894-016-3195-6

Cited by 17 publications

(11 citation statements)

References 68 publications

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“…hydrogen bonding) between solute and solvent molecules. Interestingly, inclusion of nonelectrostatic terms to IEF-PCM by SMD approach does not show any significant changes in the geometries in contrast to our former results [41]. It may be concluded that steric factors dominate over all other possible factors effecting geometries for the investigated systems.…”

Section: Resultscontrasting

confidence: 76%

“…3. In our former DFT study [41], our results indicate that formation of the TacSac complex requires energy (EC values vary between +5 to +12 kcal/mol) and is a nonspontaneous endergonic process with ΔΔG values around +10 kcal/mol. However, in current study, MP2 results revealed a quite oppposite tendency.…”

Section: Resultsmentioning

confidence: 63%

“…The initial geometries obtained from the conformational research in our previous work [41] were used for Tac, Sac and TacSac. The structures of investigated systems were visualized by Gaussview 5.0.9 [42].…”

Section: Methodsmentioning

confidence: 99%

“…There are many studies reported on tacrine and saccharin; but, neither experimental nor computational studies are reported on the tacrinesaccharin complex formed by the reaction of tacrine and saccharin to form an amidine (TacSac, Fig. 3) except our recent computational study [41]. We investigated the spectroscopic properties of TacSac using density functional theory (DFT) and timedependent density functional theory (TDDFT) with different functionals.…”

Section: Fig 2 Five Amidine Classes Described By Shriner and Neumannmentioning

confidence: 99%

“…This observation is similar to our former DFT results. In our previous study, we performed TD-DFT calculations to obtain UV-Vis spectra with different functionals on ground state geometries obtained at B3LYP/6-311++G(d,p) level using the first 40 singlet states [41]. The experimental and computational results were in good agreement but because of the discrepancies in the optimized TacSac geometries, the calculations were repeated with ground state geometries obtained at MP2/6-311++G(d,p) level.…”

Section: Etot (Zpe)mentioning

confidence: 99%

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The amidine formed by tacrine and saccharin revisited: An ab initio Investigation of Structural, Electronic and Spectroscopic Properties

Açar

2019

Turkish Computational and Theoretical Chemistry

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Computational study of tacrine and saccharin and their amidine complex (TacSac) was peformed by ab initio calculations including electron correlation. Structure, UV-Vis spectra and charge distribution of the amidine (TacSac) were investigated using ground state geometries optimized at MP2/6-311++G(d,p) level. The effects of solvent was investigated using polarizable continuum model (PCM) in conjunction with the solvation model based on density (SMD) approach. TacSac geometry remained same in gas phase and in H2O both with PCM and SMD models in contrast to former DFT results. The amidine is calculated to be stable indicating that former DFT calculations underestimated the stability of the investigated amidine. UV-Vis spectra and electronic transitions were calculated at CIS/6-311++G(d,p), B3LYP/6-311++G(d,p) and CAM-B3LYP/6-311++G(d,p) levels of theory and B3LYP gave the best results. TacSac has a peak at a higher wavelength enabling S0→S1 transition with a lower energy. S0→S1 transition corresponds to full charge transfer between HOMO and LUMO orbitals of TacSac in H2O. The ab initio results indicate that the TacSac system can be synthesized with an easy condensation reaction, and that the amidine product is a potential candidate for photochemical charge-transfer systems.

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Section: Resultscontrasting

confidence: 76%

Section: Resultsmentioning

confidence: 63%

Section: Methodsmentioning

confidence: 99%

Section: Fig 2 Five Amidine Classes Described By Shriner and Neumannmentioning

confidence: 99%

Section: Etot (Zpe)mentioning

confidence: 99%

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The amidine formed by tacrine and saccharin revisited: An ab initio Investigation of Structural, Electronic and Spectroscopic Properties

Açar

2019

Turkish Computational and Theoretical Chemistry

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Structure–activity relationship of tacrine and its analogues in relation to inhibitory activity against Alzheimer’s disease

et al. 2019

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An efficient eco-friendly, simple, and green synthesis of some new spiro-N-(4-sulfamoyl-phenyl)-1,3,4-thiadiazole-2-carboxamide derivatives as potential inhibitors of SARS-CoV-2 proteases: drug-likeness, pharmacophore, molecular docking, and DFT exploration

El-Saghier,

Enaili,

Abdou

et al. 2023

Mol Divers

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Introduction The coronavirus disease 2019 (COVID-19) pandemic has caused a global health crisis. The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is a highly contagious virus that can cause severe respiratory illness. There is no specific treatment for COVID-19, and the development of new drugs is urgently needed. Problem statement The SARS-CoV-2 main protease (Mpro) enzyme is a critical viral enzyme that plays a vital role in viral replication. The inhibition of Mpro enzyme can be an effective strategy for developing new COVID-19 drugs. Methodology An efficient operationally simple and convenient green synthesis method had been done towards a series of novel spiro-N-(4-sulfamoylphenyl)-2-carboxamide derivatives, in ethanol at room temperature in green conditions, up to 90% yield. The molecular structures of the synthesized compounds were verified using spectroscopic methods.The title compounds were subjected to in silico analysis, including Lipinski’s rule and ADMET prediction, in addition to pharmacophore modeling and molecular docking against the active site of SARS-CoV-2 target main protease (Mpro) enzyme (6LU7). Furthermore, both of the top-ranked compounds (5 and 6) and the standard Nirmatrelvir were subjected to DFT analysis. Findings The synthesized compounds exhibited good binding affinity to SARS-CoV-2 Mpro enzyme, with binding energy scores ranging from − 7.33 kcal/mol (compound 6) and − 7.22kcal/mol (compound 5) to − 6.54 kcal/mol (compounds 8 and 9). The top-ranked compounds (5 and 6) had lower HOMO–LUMO energy difference (ΔE) than the standard drug Nirmatrelvir. This highlights the potential and relevance of charge transfer at the molecular level. Recommendation These findings suggest that the synthesized spiro-N-(4-sulfamoylphenyl)-2-carboxamide derivatives could be potential candidates for COVID-19 drug development. To confirm these drugs' antiviral efficacy in vivo, more research is required. With very little possibility of failure, this proven method could aid in the search for the SARS-CoV-2 pandemic's desperately needed medications. Graphical abstract

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DFT and TDDFT investigation of the Schiff base formed by tacrine and saccharin

Cited by 17 publications

References 68 publications

The amidine formed by tacrine and saccharin revisited: An ab initio Investigation of Structural, Electronic and Spectroscopic Properties

The amidine formed by tacrine and saccharin revisited: An ab initio Investigation of Structural, Electronic and Spectroscopic Properties

Structure–activity relationship of tacrine and its analogues in relation to inhibitory activity against Alzheimer’s disease

An efficient eco-friendly, simple, and green synthesis of some new spiro-N-(4-sulfamoyl-phenyl)-1,3,4-thiadiazole-2-carboxamide derivatives as potential inhibitors of SARS-CoV-2 proteases: drug-likeness, pharmacophore, molecular docking, and DFT exploration

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