Vitamin E models. Conformational analysis and stereochemistry of tetralin, chroman, thiochroman and selenochroman

Setiadi, David H.; Chass, Gregory A.; Torday, Ladislaus L.; Varró, András; Papp, Julius Gy.

doi:10.1016/s0166-1280(02)00299-3

Cited by 18 publications

(14 citation statements)

References 14 publications

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“…Our theoretical results indicated that the so-called “half-boat” conformation is the highly preferred low-energy form Figure 3 a which is in agreement with experimental data obtained for structurally related compounds [ 32 , 33 , 34 ]. Considering that all these compounds adopt similar low flexible conformations, it is clear that this would not be the cause of the different activities displayed against fungi.…”

Section: Resultssupporting

confidence: 90%

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

et al. 2013

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Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5–17 obtained from 1–3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.

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Section: Resultssupporting

confidence: 90%

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

et al. 2013

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“…The values of the torsion angles, C5-C10-C9-C8, C10-C9-C8-C7 and C9-C8-C7-C6, in the nonaromatic fused ring slightly deviated from those for nonsubstituted tetralin (Table S1). [11] Crystal packing and intermolecular interactions. The studied compound crystallized in the monoclinic P21/c space group.…”

Section: Resultsmentioning

confidence: 99%

Self‐Assembly and Biorecognition of a Spirohydantoin Derived from α‐Tetralone: Interplay between Chirality and Intermolecular Interactions

et al. 2020

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“…Setiadi et al . studied the molecular geometries and activation energy for ring inversions of chroman on a DFT level of theory.…”

Section: Introductionmentioning

confidence: 99%

Determination of the relationship between theoretical vibrational frequencies and experimental IR absorbance bands in organic molecules: computational study of oxane, chromane and flavan

Kuo

Bezuidenhoudt

Conradie

2013

J. Phys. Org. Chem.

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The most stable isomers of oxane, chroman and flavan as basic building blocks for flavonoids were determined by density functional methods. Excellent agreement between the theoretical vibrational frequencies and the experimental infrared (IR) absorbance spectra were obtained. Similarities and differences between the spectra of chroman and flavan were identified. The difference in the IR spectra of the two conformers of flavan, mainly related to the vibration of atoms near the stereogenic centre, makes it possible to distinguish between them. Copyright © 2013 John Wiley & Sons, Ltd.

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Vitamin E models. Conformational analysis and stereochemistry of tetralin, chroman, thiochroman and selenochroman

Cited by 18 publications

References 14 publications

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Self‐Assembly and Biorecognition of a Spirohydantoin Derived from α‐Tetralone: Interplay between Chirality and Intermolecular Interactions

Determination of the relationship between theoretical vibrational frequencies and experimental IR absorbance bands in organic molecules: computational study of oxane, chromane and flavan

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