Structural, spectroscopic and molecular docking studies on 2-amino-3-chloro-5-trifluoromethyl pyridine: A potential bioactive agent

Asath, R. Mohamed; Premkumar, R.; Mathavan, T.; Benial, A. Milton Franklin

doi:10.1016/j.saa.2016.11.037

Cited by 57 publications

(13 citation statements)

References 41 publications

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“…The corresponding modes were observed at 1286 and 1228 cm −1 in FT‐IR spectrum and 1318, 1289, 1230, and 1139 cm −1 in FT‐Raman spectrum. The CH out of plane bending vibration occurs in the region of 950‐600 cm −1 40 . In BICA molecule, the calculated CH out of plane bending vibrational modes was observed at 939, 916, and 829 cm −1 .…”

Section: Resultsmentioning

confidence: 89%

“…The corresponding mode was observed at 3104 cm −1 in FT‐IR and 3186, 3106 cm −1 in FT‐Raman spectra with 100% and 93% PED contribution. The aromatic CH in‐plane bending frequencies appear in the region 1500‐1100 cm −1 40 . The CH in plane bending vibrational mode was calculated at 1303, 1292, 1219 and 1146 cm −1 .…”

Section: Resultsmentioning

confidence: 95%

“…The HOMO‐LUMO molecular orbitals and their resulting energy gap of the molecule help to characterize the chemical reactivity and kinetic stability of the molecule 40 . The HOMO and LUMO plots in the Figure 5, which shows the charge transfer within molecule.…”

Section: Resultsmentioning

confidence: 99%

“…Local reactivity descriptors such as Fukui functions (

f_{k}^{+}, f_{k}^{-}, f_{k}^{0}

), local softness (

s_{k}^{+}, s_{k}^{-}, s_{k}^{0}

) and dual descriptor ( Δf k ) were proposed to describe the site selectivity or local reactivity of the molecule. The values of Fukui functions (

f_{k}^{+}, f_{k}^{-}, f_{k}^{0}

) were calculated from the equations,

f_{k}^{+} = q_{k} ((), N + 1) - q_{k} ((), N) for nucleophilic attack

f_{k}^{_} = q_{k} ((), N - 1) - q_{k} ((), N) for electrophilic attack

f_{k}^{0} = q_{k} ((), N + 1) - q_{k} ((), N - 1) for radical attack,

where N, N‐1, N+1 are the total electrons in neutral, cation and anion site of the molecule respectively 40,45 . The values of

f_{k}^{+}

f_{k}^{_}

and

f_{k}^{0}

describe the reactivity of k th atom towards nucleophilic attack (acting as an electrophile), electrophilic attack (acting as a nucleophile), and free radical attack (acting as a free radical).…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

“…Local reactivity descriptors such as Fukui functions (

f_{k}^{+}, f_{k}^{-}, f_{k}^{0}

), local softness (

s_{k}^{+}, s_{k}^{-}, s_{k}^{0}

) and dual descriptor ( Δf k ) were proposed to describe the site selectivity or local reactivity of the molecule. The values of Fukui functions (

f_{k}^{+}, f_{k}^{-}, f_{k}^{0}

) were calculated from the equations,

f_{k}^{+} = q_{k} ((), N + 1) - q_{k} ((), N) for nucleophilic attack

f_{k}^{_} = q_{k} ((), N - 1) - q_{k} ((), N) for electrophilic attack

f_{k}^{0} = q_{k} ((), N + 1) - q_{k} ((), N - 1) for radical attack,

where N, N‐1, N+1 are the total electrons in neutral, cation and anion site of the molecule respectively 40,45 . The values of

f_{k}^{+}

f_{k}^{_}

and

f_{k}^{0}

describe the reactivity of k th atom towards nucleophilic attack (acting as an electrophile), electrophilic attack (acting as a nucleophile), and free radical attack (acting as a free radical).…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

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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“…The symmetric N–H stretching mode of vibration is observed at 3320 cm −1 in FTIR with strong intensity. The NH 2 deformation or scissoring mode of vibration usually falls in the range 1650–1580 cm −1 [25,26]. In case of 4-amino-2-methylquinoline, the vibrational mode at 1659 cm −1 is assigned to NH 2 deformation mode [27].…”

Section: Resultsmentioning

confidence: 99%

Quantum chemical studies and spectroscopic investigations on 2-amino-3-methyl-5-nitropyridine by density functional theory

Sivaprakash

Prakash²,

Mohan³

2019

Heliyon

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Quantum chemical calculations on energy and molecular structure of 2-amino-3-methyl-5-nitropyridine (2A3M5NP) have been attempted by implementing DFT/B3LYP method using 6-311G (d,p), 6-311G++ (d,p) and cc-pVTZ basis sets. The optimized geometry and the vibrational analysis for energetically most stable configuration, are carried out theoretically by using B3LYP/cc-pVTZ basis set. The computed vibrational frequencies were scaled by using scaling factors and compared with the experimental Fourier Transform Infra-Red (FTIR) solid phase spectrum in the region 4000-400 cm −1 and FT-Raman spectrum in the region 4000-100 cm −1 . The complete vibrational assignments, analysis and correlation of fundamental modes of the compound have been carried out using the potential energy distribution (PED). The intramolecular charge transfer, hyperconjugative interaction of the compound is investigated from natural bonding orbital (NBO) analysis. The UV-Visible spectrum of 2A3M5NP was obtained with ethanol as a solvent. The electronic properties such as HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) energies are determined by B3LYP/cc-pVTZ basis set. The electronic absorption spectrum of the compound was studied from UV-Visible analysis by using time-dependent density functional theory (TD-DFT). The electron density distribution and chemical reactive sites of 2A3M5NP were analyzed from molecular electrostatic potential (MEP) analysis and frontier molecular orbital (FMO) analysis.

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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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Structural, spectroscopic and molecular docking studies on 2-amino-3-chloro-5-trifluoromethyl pyridine: A potential bioactive agent

Cited by 57 publications

References 41 publications

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

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

Quantum chemical studies and spectroscopic investigations on 2-amino-3-methyl-5-nitropyridine by density functional theory

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

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