Substituted 5-Nitro-1,3-dioxanes: Correlation of Chemical Structure and Antimicrobial Activity

Lappas, Lewis C.; Hirsch, Clarence A.; Winely, C. L.

doi:10.1002/jps.2600650910

Cited by 15 publications

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“…They have also been reported as biologically active compounds with anti-in ammatory properties, and effective modulators of multidrug resistance [3]. These compounds have also been considered for their enormous potential in terms of structural diversity, especially by substitution at positions 2 and 5 of the molecule [4,5]. 1,3 substituted molecules were found to display signi cant antifungal and antibacterial properties.…”

Section: Introductionmentioning

confidence: 99%

“…1,3 substituted molecules were found to display signi cant antifungal and antibacterial properties. Within this family of compounds, the most prominent have been the nitro and halonitro derivatives, especially because of their stability at a wider pH range (5)(6)(7)(8)(9). For instance, 5-bromo-5-nitro-1,3-dioxane (bronidox) exhibits a broad spectrum of antimicrobial activity [5] and is an important reagent for ion-radical and oxide-reduction type reactions [2 -6].…”

Section: Introductionmentioning

confidence: 99%

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Computational investigation of thermal decomposition mechanism of 5-nitro-5-R-1,3-dioxane compounds

2022

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This paper features the results of the computational study of thermal decomposition reaction of 5-nitro-5-R-1,3-dioxane compounds, with R=H, Br and CH 3 . Computational calculations were performed on M06-2X/6-311+G(d,p) in gas phase and also in solution with DMSO, at different temperatures. The kinetic and thermodynamic data obtained indicate a favoring of the reaction when the molecule presents a CH 3 substituent group in position 5 and when carried out in DMSO, the stability of the molecules in their energetic components was discussed, too. For R=H two different reaction mechanisms were proposed and studied. Wiberg bonds indices were obtained for the reactions studied and the results were examined in terms of bond formation and bond breaking progress as well.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Computational investigation of thermal decomposition mechanism of 5-nitro-5-R-1,3-dioxane compounds

2022

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ChemInform Abstract: SUBSTITUTED 5‐NITRO‐1,3‐DIOXANES‐ CORRELATION OF CHEMICAL STRUCTURE AND ANTIMICROBIAL ACTIVITY

Lappas¹,

Hirsch²,

Winely³

1977

Chemischer Informationsdienst

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Configurational analysis of diastereomeric open‐chain and cyclic nitro‐substituted diols by NMR spectroscopy

Sohár¹,

Mikite²,

Pelczer³

et al. 1984

Org. Magn. Reson.

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Nitro-substituted 1,3-dioxanes and pyrans with potential biological activity were synthesized. The relative configurations of the threo and erythro isomers of 2-nitro-l-phenylpropane-1,3-diol (the starting materials) and of 5-nitro-2,4-diphenyl-1,3-dioxane, the products formed with benzaldehyde, were determined by 'H and =C NMR spectroscopy. Ciamaldehyde and nitroethanol give a homologue of nitrophenylpropanediol, which exists as a mixture of two diastereomeric cyclic hemiacetals. After dissolving in CDCI,, the ratio of these components changes &om approximately 10 : 1 to 3 : 2 in a few days. The ethyl acetal of the hemiacetal is stereohomogeneous, and the ethoxy group is axial to the pyran ring owing to the anomeric effect. This configuration was proved by two-dimensional NMR measurement, permitting separate observation of the originally overlapping mnltiplets and direct reading of the H,H coupling constants.

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Substituted 5-Nitro-1,3-dioxanes: Correlation of Chemical Structure and Antimicrobial Activity

Cited by 15 publications

References 3 publications

Computational investigation of thermal decomposition mechanism of 5-nitro-5-R-1,3-dioxane compounds

Computational investigation of thermal decomposition mechanism of 5-nitro-5-R-1,3-dioxane compounds

ChemInform Abstract: SUBSTITUTED 5‐NITRO‐1,3‐DIOXANES‐ CORRELATION OF CHEMICAL STRUCTURE AND ANTIMICROBIAL ACTIVITY

Configurational analysis of diastereomeric open‐chain and cyclic nitro‐substituted diols by NMR spectroscopy

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