Synthesis and DFT calculation on novel derivatives of Bis (indolyl) methanes

Zarandi, Maryam; Beni, Alireza Salimi

doi:10.1016/j.molstruc.2016.04.082

Cited by 10 publications

(12 citation statements)

References 28 publications

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“…In the experimental spectra the symmetrical and asymmetrical stretching bands were observed in the ranges of 3100–3000, 3000–2900 and 2900–2800 cm −1 , respectively. The theoretically scaled frequency and the experimental data were in agreement [ 27 , 28 ].…”

Section: Resultsmentioning

confidence: 61%

“…The calculated band appeared in the range of 1360–1330 cm −1 , in other words, the theoretical and experimental values are in accordance. The B–C stretching band according to the literature is found in the range of 1080 and 1110 cm −1 or up to 1300 cm −1 [ 3 , 14 , 15 , 27 , 28 , 29 ]. For the studied molecules, the experimental bands were found close to 1090 cm −1 meanwhile the calculated values were around 1100–1070 cm −1 .…”

Section: Resultsmentioning

confidence: 96%

“…The C=C stretching and bending in aromatic compounds are usually found between 1620–1680 cm −1 and 1500–1700 cm −1 , respectively. In the target compounds, intense bands around 1700 cm −1 were obtained in the experimental procedure and in the computed values these were perceived in the range of 1630–1580 cm −1 ; these correspond to the symmetrical stretching of the indolylic moiety and the benzene ring [ 27 , 28 ]. An experimental band around 1600 cm −1 was assigned to the asymmetrical stretch of the indole and the benzene ring, in addition to the bending of C–H and N–H bonds, that were correlated with the theoretical values at 1580–1490 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

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A DFT Study of the Geometrical, Spectroscopical and Reactivity Properties of Diindolylmethane-Phenylboronic Acid Hybrids

et al. 2017

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The structure of the ortho-, meta- and para- hybrid diindolylmethane-phenylboronic acids and their interactions were optimized with by a quantum chemical method, using density functional theory at the (DFT) level. Thus, infrared bands were assigned based on the scaled theoretical wavenumbers by correlating the respective experimental data of the molecules. In addition, the corresponding 1H-/13C-/11B-NMR experimental and theoretical chemical shifts were correlated. The target molecules showed a poor treatment of the OH shifts in the GIAO method due to the absence of explicit solvent effects in these calculations; therefore, they were explicitly considered with acetone molecules. Moreover, the electron density at the hydrogen bond critical point increased, generating stabilization energy, from weak to moderate or weak to strong, serving as an indicator of the strength of the hydrogen bond between the different intermolecular interactions. Finally, some properties related to the reactive behavior of the target molecules associated with their cytotoxic effects and metabolic pathways were also calculated.

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Section: Resultsmentioning

confidence: 61%

Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

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A DFT Study of the Geometrical, Spectroscopical and Reactivity Properties of Diindolylmethane-Phenylboronic Acid Hybrids

et al. 2017

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“…A broad peak observed at 3432 cm −1 with 100% PED contribution in FT‐IR spectrum was identified as NH stretching frequency which is theoretically calculated at 3613 cm −1 . The effect of NH…π interaction influences the NH stretching frequency and shifted to the lower frequency region 34,35 . The NH in plane bending vibration was calculated at 1422 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

Vibrational, spectroscopic, chemical reactivity, molecular docking and in vitro anticancer activity studies against A549 lung cancer cell lines of 5‐Bromo‐indole‐3‐carboxaldehyde

S¹,

A²,

Kaviyarasu

2020

J of Molecular Recognition

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Spectroscopic investigations are performed for 5‐Bromo‐1H‐indole‐carboxaldehyde by using experimental (FT‐IR, FT‐Raman) and theoretical (DFT) calculations. Vibrational assignments of the fundamental modes were assigned on the basis of Potential energy distribution (PED) calculations. Electron Localization Function (ELF) and Local Orbital Localizer (LOL) studies were performed to visualize the electron delocalization in the molecule. Frontier molecular orbitals (FMOs) and related molecular properties were computed. The electron‐hole distribution of the molecule was also computed using Multiwfn 3.3.9 software to predict the charge transfer within the molecule. The total and partial density of states (TDOS and PDOS) and also the overlap population density of states (OPDOS) spectra were simulated. UV‐Vis spectrum of the compound was also recorded. The reactive sites of the compound were studied from the MEP and Fukui function analysis. The charge delocalization and stability of the title molecule were investigated using natural bond orbital (NBO) analysis. The lung cancer activity of the title compound against p53 tumor suppressor proteins was studied using molecular docking analysis. The in‐vitro cytotoxic activity of the molecule against human pulmonary lung cancer cell lines (A549) was determined by MTT assay.

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“…The N H in-plane bending vibration was reported in the wavenumber region of 1412 to 1415 cm −1 . 41,42 The strong peak was observed at 1436 cm −1 in FT-IR, and FT-Raman spectrum corresponds to N H in-plane bending mode. The corresponding mode was calculated as 1431 cm −1 with 20% contribution in total PED.…”

Section: N H Vibrationmentioning

confidence: 99%

Spectroscopic characterization, DFT studies, molecular docking and cytotoxic evaluation of 4‐nitro‐indole‐3‐carboxaldehyde: A potent lung cancer agent

Jeyaseelan¹,

Benial²

2020

J of Molecular Recognition

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The 4-nitro-1H-indole-carboxaldehyde (NICA) molecule was characterized experimentally using FT-IR, FT-Raman and UV-Vis spectra, and it was studied theoretically using DFT calculations. The optimized structure of the NICA molecule was determined by DFT calculations using B3LYP functional with cc-pVTZ basis set. The electron localization function (ELF) and local orbital localizer (LOL) studies were performed to visualize the electron delocalization in the molecule. The experimental and theoretical wavenumbers of the title molecule were assigned using VEDA 4.0 program. The charge delocalization and stability of the title molecule were investigated using natural bond orbital (NBO) analysis. Frontier molecular orbitals (FMOs) and related molecular properties were calculated. UV-Vis spectrum was calculated theoretically and validated experimentally. The reactive sites of the molecule were studied from the MEP surface and Fukui function analysis. The molecular docking analysis reveals that the NICA ligand shows better inhibitory activity against RAS, which causes lung cancer. The in vitro cytotoxic activity of the molecule against human lung cancer cell lines (A549) was determined by MTT assay. Thus, the NICA molecule can be used as a potential candidate for the development of the drug against lung cancer.

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Synthesis and DFT calculation on novel derivatives of Bis (indolyl) methanes

Cited by 10 publications

References 28 publications

A DFT Study of the Geometrical, Spectroscopical and Reactivity Properties of Diindolylmethane-Phenylboronic Acid Hybrids

A DFT Study of the Geometrical, Spectroscopical and Reactivity Properties of Diindolylmethane-Phenylboronic Acid Hybrids

Vibrational, spectroscopic, chemical reactivity, molecular docking and in vitro anticancer activity studies against A549 lung cancer cell lines of 5‐Bromo‐indole‐3‐carboxaldehyde

Spectroscopic characterization, DFT studies, molecular docking and cytotoxic evaluation of 4‐nitro‐indole‐3‐carboxaldehyde: A potent lung cancer agent

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