Quantitative structure-activity relationships of cardiotonic steroids using empirical molecular electrostatic potentials and semiempirical molecular orbital calculations

Bohl, Martin; Ponsold, K.; Reck, G.

doi:10.1016/0022-4731(84)90299-1

Cited by 9 publications

(6 citation statements)

References 32 publications

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“…Molecular electrostatic potentials (MEP) have been shown to correlate with experimentally based quantities such as σ I , σ R , p K a , α, and β (solvatochromic H bond donor and acceptor parameters). Thus, it is probably not surprising that MEP values, often minima or maxima, have been shown to relate to biological properties such as inotropes, the methylation of DNA bases, anti-HIV activity, and several other responses. , Charged partial surface areas have been computed and applied to the prediction of a variety of experimental physicochemical properties, − and although they have not been applied extensively to biological properties it has been suggested that they have much potential in this area . Blaney and co-workers have reported a system for the comparison of molecular surface properties and have shown the application of electrostatic potential and shape properties to the study of β-lactam antibiotics and phosphodiesterase inhibitors.…”

Section: Calculated Propertiesmentioning

confidence: 99%

The Characterization of Chemical Structures Using Molecular Properties. A Survey

Livingstone

1999

J. Chem. Inf. Comput. Sci.

245

155

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Section: Calculated Propertiesmentioning

confidence: 99%

The Characterization of Chemical Structures Using Molecular Properties. A Survey

Livingstone

1999

J. Chem. Inf. Comput. Sci.

245

155

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“…Thus, it can be asserted that MESP values have been shown to be well related to biological properties. [26][27][28]. Table 6.…”

Section: Electronic Spectra and Electronic Propertiesmentioning

confidence: 99%

Structural, Electronic, and Vibrational Properties of Isoniazid and Its Derivative N-Cyclopentylidenepyridine-4-carbohydrazide: A Quantum Chemical Study

Pandey¹,

Bajpai

Baboo

et al. 2014

Journal of Theoretical Chemistry

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Isoniazid (Laniazid, Nydrazid), also known as isonicotinylhydrazine (INH), is an organic compound that is the first-line medication in prevention and treatment of tuberculosis. The optimized geometry of the isoniazid and its derivative N-cyclopentylidenepyridine-4-carbohydrazide molecule has been determined by the method of density functional theory (DFT). For both geometry and total energy, it has been combined with B3LYP functionals having LANL2DZ and 6-311 G (d, p) as the basis sets. Using this optimized structure, we have calculated the infrared wavenumbers and compared them with the experimental data. The calculated wavenumbers by LANL2DZ are in an excellent agreement with the experimental values. On the basis of fully optimized ground-state structure, TDDFT//B3LYP/LANL2DZ calculations have been used to determine the low-lying excited states of isoniazid and its derivative. Based on these results, we have discussed the correlation between the vibrational modes and the crystalline structure of isoniazid and its derivative. A complete assignment is provided for the observed FTIR spectra. The molecular HOMO, LUMO composition, their respective energy gaps, and MESP contours/surfaces have also been drawn to explain the activity of isoniazid and its derivative.

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“…For any nucleophilic substitution reaction near oxygen (closed contour area), an amount of energy equal to the shielded potential energy surface is required; however remaining part of the molecule is suitable for electrophilic substitution reaction. us it can be asserted that MESP values have been shown to be well related to the biological properties [33][34][35].…”

Section: Some Other Modes Of Vibration At Lower Frequencies Amentioning

confidence: 99%

Quantum Mechanical Study on the Structure and Vibrational Spectra of Cyclobutanone and 1,2-Cyclobutanedione

Pandey

Dwivedi

Misra

2013

Journal of Spectroscopy

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For 1,2-cyclobutanedione and cyclobutanone, we have carried out a comparative study of different methods like B3LYP, LSDA, and B3PW91 of DFT using 6-31G (d, p) basis set and MP2 method. On comparing these methods we find that B3PW91 method is closer to the experimental one. So by using B3PW91 method, we have made a comparative study of their structures, normal mode analysis, and other properties of the two derivatives of cyclobutane. The molecular HOMO, LUMO composition, their respective energy gaps, and MESP contours/surfaces have also been drawn to explain the activity of 1,2-cyclobutanedione and cyclobutanone.

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Quantitative structure-activity relationships of cardiotonic steroids using empirical molecular electrostatic potentials and semiempirical molecular orbital calculations

Cited by 9 publications

References 32 publications

The Characterization of Chemical Structures Using Molecular Properties. A Survey

The Characterization of Chemical Structures Using Molecular Properties. A Survey

Structural, Electronic, and Vibrational Properties of Isoniazid and Its Derivative N-Cyclopentylidenepyridine-4-carbohydrazide: A Quantum Chemical Study

Quantum Mechanical Study on the Structure and Vibrational Spectra of Cyclobutanone and 1,2-Cyclobutanedione

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