DFT, Hirshfeld surfaces, spectral and in vivo cytotoxic studies of 7a-Aza-B-homostigmast-5-eno [7a,7-d] tetrazole

Alam, Mahboob; Nami, Shahab A.A.; Khan, Mohd. Shahid; Ahmad, Shabbir; Lee, Dong‐Ung

doi:10.1016/j.molstruc.2015.07.017

Cited by 22 publications

(3 citation statements)

References 38 publications

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“…The calculated chemical shifts of carboxylic carbon atoms are predicted at 176.17 (C3) and 175.17 (C7) ppm. This is because carbonyl carbon atoms are connected to more electronegative oxygen atom that withdraws the electron from the carbon atom [64]. The signals due to carbon atoms (C]N, C]CeN) of ring were found at 162.79 and 154.97 ppm which correspond to C26 and C20 of pyrimidine moiety respectively.…”

Section: C and 1 H Nmr Spectramentioning

confidence: 99%

Growth, structure, Hirshfeld surface and spectroscopic properties of 2-amino-4-hydroxy-6-methylpyrimidinium-2,3-pyrazinedicorboxylate single crystal

Faizan

Ahmad

Afroz

et al. 2018

Journal of Molecular Structure

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The present work is focused on the crystal structure, vibrational spectroscopy and DFT calculations of hydrogen bonded 2,3-pyrazinedicorboxylic acid and 2-amino-4-hydroxy-6-methylpyrimidine (PDCA À .AHMP þ) crystal. The crystal structure has been determined using single crystal X-ray diffraction analysis which shows that the crystal belongs to monoclinic space group P2 1 /n. The PDCA À .AHMP þ crystal has been characterized by FTIR, FT-Raman and FT-NMR spectroscopic techniques. The FTIR and FT-Raman spectra of the complex have unique spectroscopic feature as compared with those of the starting material to confirm salt formation. The theoretical vibrational studies have been performed to understand the modes of the vibrations of asymmetric unit of the complex by DFT methods. Hirschfeld surface and 2D fingerprint plots analyses were carried out to investigate the intermolecular interactions and its contribution in the building of PDCA À .AHMP þ crystal. The experimental and simulated 13 C and 1 H NMR studies have assisted in structural analysis of PDCA À .AHMP þ crystal. The electronic spectroscopic properties of the complex were explored by the experimental as well as theoretical electronic spectra simulated using TD-DFT/IEF-PCM method at B3LYP/6-311þþG (d,p) level of theory. In addition, frontier molecular orbitals, molecular electrostatic potential map (MEP) and nonlinear optical (NLO) properties using DFT method have been also presented.

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Section: C and 1 H Nmr Spectramentioning

confidence: 99%

Growth, structure, Hirshfeld surface and spectroscopic properties of 2-amino-4-hydroxy-6-methylpyrimidinium-2,3-pyrazinedicorboxylate single crystal

Faizan

Ahmad

Afroz

et al. 2018

Journal of Molecular Structure

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“…The drift of the investigational values obtained by experimentation is primarily due to the structural features and the physical state of the sample . The C−O stretching vibrations of the acetoxy group bonded to position 3 of the steroidal skeleton display of two asymmetric coupled vibrations i. e., CH 3 ‐C(=O)‐O‐ and –C(=O)‐O−C‐(steroidal skeleton), the first stretching is more significant.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic Identifications, Molecular Docking, Neuronal Growth and Enzyme Inhibitory Activities of Steroidal Nitro Olefin: Quantum Chemical Study

Alam

Park

2019

ChemistrySelect

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FT‐IR, NMR and ultraviolet spectroscopy by means of DFT / B3LYP‐6‐311G(d, p), molecular docking and biological activity of 6‐nitrocolest‐5‐en‐3‐beta‐yl acetate (steroid nitro‐olefin) was reported in this article. The optimized molecular geometric structure and its associated parameters including vibrational frequencies, carbon and 1H NMR data of the title compound in ground electronic state was obtained at DFT approach applying B3LYP/6‐311G(d,p). The ultraviolet absorbance data is obtained at TDB3LYP/6‐311G(d,p) basis set. The present computational data are found in reasonable agreement with the experimental results. Simulated electronic and NMR (1H and 13C) spectra have been reported in solution phase. Parameters like thermodynamic quantities, dipole moment, FMO energies, MEP and global reactivity descriptors of steroid nitro olefin were determined at same level of theory. The neuromodulatory effect of the compound on central nervous system development of rat embryonic hippocampal neurons has been studied. Based on the outcome; compound demonstrated suppression activity despite the promotion of neuronal cytoarchitecture leading to a negative effect on hippocampal neurons. The nature of the compound found to be toxic to the cells. Besides, steroid compound is also used to perform inhibitory activity against acetylcholinesterase (AChE) compared to the reference drug i. e. Galanthamine. The molecular docking of the synthesized compound is carried out with the structure of the acetylcholinesterase (PDB: 1DX6) protein to check the mode of interactions.

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“…Also Electron withdrawing substituents shift the equilibrium the azide isomer, in some cases, the tetrazole isomer cannot be isolated. The molecular structure, IR, NMR spectra and various other molecular properties of 7a-Aza-B-homostigmast-5-eno tetrazole have been computed using B3LYP method with 6-311G(2d,p) level of theory by Mahboob Alam and coworkers [11]. They simulated the NMR spectra in gaseous and solution phase (using PCM model) by GIAO approach at same level of theory.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure, NMR, FMO, MEP and NBO Analysis of ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate Based on HF and DFT Calculations

2017

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In the present work, for the first time the quantum calculations of Ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate are evaluated using the HF and B3LYP methods with 6-311++G** basis set. The geometry of the title compound was optimized by B3LYP/6-311++G** level of theory. The theoretical 1 H and 13 C NMR chemical shift values of the title compound are calculated and compared with the experimental results. The computed data are in good agreement with the experimental data. Frontier molecular orbitals (FMOs), molecular electrostatic potential (MEP), energy gap between HOMO and LUMO, electronic properties, thermodynamic parameters, natural charges distribution (NBO charges) and NBO analysis were investigated and discussed by theoretical calculations. KEYWORDSTetrazole DFT natural charge NBO analysis electronic properties Graphical AbstractMolecular structure, NMR, FMO… P a g e | 33

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DFT, Hirshfeld surfaces, spectral and in vivo cytotoxic studies of 7a-Aza-B-homostigmast-5-eno [7a,7-d] tetrazole

Cited by 22 publications

References 38 publications

Growth, structure, Hirshfeld surface and spectroscopic properties of 2-amino-4-hydroxy-6-methylpyrimidinium-2,3-pyrazinedicorboxylate single crystal

Growth, structure, Hirshfeld surface and spectroscopic properties of 2-amino-4-hydroxy-6-methylpyrimidinium-2,3-pyrazinedicorboxylate single crystal

Spectroscopic Identifications, Molecular Docking, Neuronal Growth and Enzyme Inhibitory Activities of Steroidal Nitro Olefin: Quantum Chemical Study

Molecular Structure, NMR, FMO, MEP and NBO Analysis of ethyl-(Z)-3-phenyl-2-(5-phenyl-2H-1,2,3,4-tetraazol-2-yl)-2-propenoate Based on HF and DFT Calculations

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