Molecular docking, spectroscopic studies on 4-[2-(Dipropylamino) ethyl]-1,3-dihydro-2H-indol-2-one and QSAR study of a group of dopamine agonists by density functional method

Kuruvilla, Tintu K.; Muthu, S.; Prasana, Johanan Christian; George, Jacob; Saji, Rinnu Sara; S, Ben Geoffrey A; David, Rolf

doi:10.1016/j.saa.2019.117185

Cited by 8 publications

(4 citation statements)

References 29 publications

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“…The biological activity of a compound is closely related to its electronic structure. The importance of HOMO and LUMO with regard to that issue has been emphasized many times by several authors [24,49,50]. In particular, the HOMO orbital energy, E HOMO , can be correlated with the electron-donating character, in that the higher (less negative) the energy, the more electron donating ability of the molecule.…”

Section: Resultsmentioning

confidence: 99%

“…The DFT results were used in the QSAR analysis, among others, for the evaluation of antibacterial activities against Gram-positive ( Staphylococcus aureus ) and Gram-negative bacteria ( Klebsiella pneumonia , Proteus bacilli , and Shigella flexneri ) of quinazolinone compounds [23]. In turn, Kuruvilla et al [24] calculated, inter alia, the HOMO and LUMO energies using the DFT method, and the obtained results were used in the QSAR analysis to understand the stability, reactivity, and bioactivity of the test compound (4-[2-(Dipropylamino) ethyl]-1,3-dihydro-2H-indol-2-one).…”

Section: Introductionmentioning

confidence: 99%

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Meat Proteins as Dipeptidyl Peptidase IV Inhibitors and Glucose Uptake Stimulating Peptides for the Management of a Type 2 Diabetes Mellitus In Silico Study

et al. 2019

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Diabetes mellitus is a non-communicable disease entity currently constituting one of the most significant health problems. The development of effective therapeutic strategies for the prevention and/or treatment of diabetes mellitus based on the selection of methods to restore and maintain blood glucose homeostasis is still in progress. Among the different courses of action, inhibition of dipeptidyl peptidase IV (DPP-IV) can improve blood glucose control in diabetic patients. Pharmacological therapy offering synthetic drugs is commonly used. In addition to medication, dietary intervention may be effective in combating metabolic disturbances caused by diabetes mellitus. Food proteins as a source of biologically active sequences are a potential source of anti-diabetic peptides (DPP-IV inhibitors and glucose uptake stimulating peptides). This study showed that in silico pork meat proteins digested with gastrointestinal enzymes are a potential source of bioactive peptides with a high potential to control blood glucose levels in patients with type 2 diabetes mellitus. Analysis revealed that the sequences released during in silico digestion were small dipeptides (with an average weight of 270.07 g mol−1), and most were poorly soluble in water. The selected electron properties of the peptides with the highest bioactivity index (i.e., GF, MW, MF, PF, PW) were described using the DFT method. The contribution of hydrophobic amino acids, in particular Phe and Trp, in forming the anti-diabetic properties of peptides released from pork meat was emphasized.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Meat Proteins as Dipeptidyl Peptidase IV Inhibitors and Glucose Uptake Stimulating Peptides for the Management of a Type 2 Diabetes Mellitus In Silico Study

et al. 2019

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“…The energy difference between HOMO and LUMO gives us the HOMO-LUMO energy gap [15] . The HOMO-LUMO energy gap plays a significant role in determining the bioactivity due to charge transfer within the molecule [16] . A molecule with high HOMO-LUMO energy gap is more stable and less reactive while a low HOMO-LUMO energy gap indicates towards its reactivity.…”

Section: Resultsmentioning

confidence: 99%

DFT study on the structural and chemical properties of Janus kinase inhibitor drug Baricitinib

Sonia

Devi

Karlo

2022

Materials Today: Proceedings

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“…Obviously, the target compound 3a had the highest ΔE of HOMO-LUMO gap, which indicated that it may have lower insecticidal and Factors (steric effects and electron donation/withdrawing properties) of 3a-g influencing the electron structure/insecticidal and fungicidal activities are described in Figures S1 and S2. According to molecular orbital theory, the highest occupied molecular orbital (HOMO) and the lowest occupied molecular orbital (LUMO) play key roles in the biological activities of agrochemicals [37,38]. HOMO represents the electron-donating ability of molecules and higher HOMO energy (EHOMO) indicates the electrons in molecules become unstable and, thus, result in the loss of electrons easily.…”

Section: Quantum Chemistry Calculations Of the Geometry And Electroni...mentioning

confidence: 99%

Design, Synthesis, and Evaluation of X-ray Crystal Structure, Biological Activities, DFT Calculations, and Molecular Docking of Phenyl Imidazolidin-2-One Derivatives

et al. 2020

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Eight phenyl imidazolinone derivatives were synthesized from N2-(2,4-dimethylphenyl)-N1-methyformamidine (DPMF) via scaffold-hopping method using the ring-closure approach. The prepared compounds were verified using 1H and 13C NMR and HRMS spectroscopies. The structure of compound 3c was confirmed by single-crystal X-ray diffraction analysis. The mean plane of the phenyl and imidazolinone moieties was almost coplanar with an angle of 8.85(4)°. In the crystal, molecules were interlinked with intermolecular hydrogen bonds (N–H···O and C–H···O), generating a network structure. Additionally, compound 3f displayed the highest insecticidal activity (86.7%) against Plutella xylostella at 600 mg/L, which was significantly higher than the insecticidal activity (23.0%) of DPMF. Also, compound 3d displayed good fungicidal activities against Phytophthora capsici, Phytophthora sojae, and Phytophthora infestans. Density functional theory (DFT) calculations were performed to explain the insecticidal and fungicidal activities of phenyl imidazolidin-2-one derivatives, especially potent compounds 3f and 3d. Moreover, the binding modes of compounds 3a–h and DPMF against octopamine receptor of Plutella xylostella were studied by homology modeling and molecular docking. Therefore, a preliminary structure–activity relationship (SAR) was derived and discussed. These results encourage the exploration of novel insecticides and fungicides based on DPMF.

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Molecular docking, spectroscopic studies on 4-[2-(Dipropylamino) ethyl]-1,3-dihydro-2H-indol-2-one and QSAR study of a group of dopamine agonists by density functional method

Cited by 8 publications

References 29 publications

Meat Proteins as Dipeptidyl Peptidase IV Inhibitors and Glucose Uptake Stimulating Peptides for the Management of a Type 2 Diabetes Mellitus In Silico Study

Meat Proteins as Dipeptidyl Peptidase IV Inhibitors and Glucose Uptake Stimulating Peptides for the Management of a Type 2 Diabetes Mellitus In Silico Study

DFT study on the structural and chemical properties of Janus kinase inhibitor drug Baricitinib

Design, Synthesis, and Evaluation of X-ray Crystal Structure, Biological Activities, DFT Calculations, and Molecular Docking of Phenyl Imidazolidin-2-One Derivatives

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