Computational study of substituent effects on the acidity, toxicity and chemical reactivity of bacteriostatic sulfonamides

Soriano-Correa, Catalina; Barrientos-Salcedo, Carolina; Francisco‐Márquez, Misaela; Sainz‐Díaz, C. Ignacio

doi:10.1016/j.jmgm.2018.02.006

Cited by 46 publications

(6 citation statements)

References 46 publications

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“…To get further insights into the molecular properties and to explain the structure–activity relationship of Oxazosulfyl analogues, we studied the electronic characteristics of selected compounds ( A5 , A18 , A20 , and Oxazosulfyl). According to the frontier molecular orbital theory proposed by Kenichi Fukui, the biological activity of molecules is linked to the ability of a molecule to provide and accept electrons, respectively, and is reflected by the calculated HOMO and LUMO energies . As shown in Figure , most occupations of the HOMOs and LUMOs of the ethylsulfonylpyridine compounds are localized around the benzoxazole and the substituted pyridine ring.…”

Section: Resultsmentioning

confidence: 99%

“…According to the frontier molecular orbital theory proposed by Kenichi Fukui, the biological activity of molecules is linked to the ability of a molecule to provide and accept electrons, respectively, and is reflected by the calculated HOMO and LUMO energies. 44 As shown in Figure 5, most occupations of the HOMOs and LUMOs of the ethylsulfonylpyridine compounds are localized around the benzoxazole and the substituted pyridine ring. Also, it is worth noting that some LUMOs were distributed in the ethanesulfonyl moiety as well, implying that this substituent probably makes a major contribution to the insecticidal activity.…”

Section: -(5-(tert-butyldimethylsilyl)-3-(ethylsulfonyl)pyridin-2-yl)...mentioning

confidence: 97%

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Synthesis and Biological Activity of Silicon-Containing Ethylsulfonylpyridine Insecticides

Xu,

Quan,

et al. 2023

J. Agric. Food Chem.

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Ethylsulfonylpyridines are a novel chemical class of insecticides with excellent broad-spectrum activity and an unprecedented mode of action. With the objective of discovering novel ethylsulfonylpyridines with a broader spectrum, wider range of uses, and/or improved properties, we have started a research program aimed at introducing silicon motifs and studying their biological effects. We designed a series of Oxazosulfyl analogues where the hydrogen atom at the 5-position of the pyridyl moiety is replaced by a trialkylsilyl group and prepared these compounds applying denovo synthetic methodology. Our novel ethylsulfonylpyridines exhibit excellent insecticidal activities. The best compound, A18, resulting from our research exhibited an LC 50 value of 0.30 mg/L against Plutella xylostella and reached the activity level of the commercial standard Oxazosulfyl. Our findings confirmed our working hypothesis that at the 5-position of the pyridyl moiety larger groups with different hydrophobic, electronic, and steric properties are tolerated.

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Section: Resultsmentioning

confidence: 99%

Section: -(5-(tert-butyldimethylsilyl)-3-(ethylsulfonyl)pyridin-2-yl)...mentioning

confidence: 97%

Synthesis and Biological Activity of Silicon-Containing Ethylsulfonylpyridine Insecticides

Xu,

Quan,

et al. 2023

J. Agric. Food Chem.

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“…These two orbitals are most interacting in the complex, and thus called frontier orbitals. [45][46][47][48] The energy gaps were computed at LANL2DZ basis set. In Scheme 1 Synthesis scheme of complex 1. complex 1, the HOMO and LUMO energies are −5.19 and −1.27 eV, respectively, leading to an energy gap of 3.92 eV (Fig.…”

Section: Computational Studiesmentioning

confidence: 99%

A novel cobalt(ii) acetate complex bearing lutidine ligand: a promising electrocatalyst for oxygen evolution reaction

et al. 2023

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“…In previous works we showed that the substitution of groups in the SO 2 N1H moiety for one of the H atoms on N1 may influence the tendency of the second H atom to participate in hydrogen bonding, that is, this region is an important interaction site. Also, the influence of the substituent group may be steric or electronic, as well as the bulky functional groups might be expected to hinder the approach of an amide H atom to the sulfonamide O atom of a neighboring molecule [ 11 ]. However, the functional group may, through the inductive effect or resonance effects at the molecular level, increase or reduce the electron density on the amide nitrogen, and consequently affecting the strength of the hydrogen bonds that might form.…”

Section: Introductionmentioning

confidence: 99%

Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations

Sainz‐Díaz

Luz

Barrientos-Salcedo

et al. 2022

J Comput Aided Mol Des

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Sulfonamides are an important class of therapeutic agents. The increase in the number of new sulfonamide derivatives makes it necessary to study more rationally the chemical structure, because the solid forms often display different mechanical, thermal and physicochemical properties that can influence the bioavailability and stability of the drugs; consequently, the polymorphic structures are of great interest to the pharmaceutical industry because of their ability to modify the physical properties of the active pharmaceutical ingredient. The molecular interactions of these drugs in their crystal lattice are important for the stability of the crystals and polymorphism and for preparing composite complexes for optimizing the use of these drugs. In this work, the crystal structure of these drugs and crystal polymorphism is investigated. So, the crystal forms of antibiotics derivatives of the sulfonamides, sulfamethoxazole, sulfamethazine, sulfachloropyridazine, and sulfacetamide are studied at the molecular and supramolecular level by using computational modeling approach at quantum mechanical level. The spectroscopic properties of these systems are also studied explaining assignments of previous experimental data. The results of DFT calculations reproduce the crystal structures of sulfonamides determined experimentally and the polymorphism in these molecules have been clarified. Likewise, the main intermolecular interactions in all crystal forms of these sulfonamides are H-bonds among the sulfonic and amino groups and SNH groups, and also some π-π interactions. Also, these 3-D periodical models allow the exploration of the intermolecular interactions included in the crystal structures and some of these interactions can alter the vibration modes of the molecules. Therefore, the use of these models can be useful for experimental spectroscopy studies where use actual crystal solids.

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Computational study of substituent effects on the acidity, toxicity and chemical reactivity of bacteriostatic sulfonamides

Cited by 46 publications

References 46 publications

Synthesis and Biological Activity of Silicon-Containing Ethylsulfonylpyridine Insecticides

Synthesis and Biological Activity of Silicon-Containing Ethylsulfonylpyridine Insecticides

A novel cobalt(ii) acetate complex bearing lutidine ligand: a promising electrocatalyst for oxygen evolution reaction

Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations

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