Silicon Analogues of the Musk Odorant Versalide

Büttner, Matthias W.; Penka, Martin; Doszczak, Leszek; Kraft, Philip; Tacke, Reinhold

doi:10.1021/om060934h

Cited by 35 publications

(18 citation statements)

References 8 publications

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“…Gane et al attribute the musk odor perception to be symptomatic of groups responsible for a strong absorption within the 1,380-1,550 cm −1 IR region. Yet a broader examination of the IR and Raman absorptions of musks, including popular nitro-musks, structurally similar non-musks, and recently examined silio-musks (see [90]), show no clean relationship between musk odor and any single spectral feature.…”

Section: Methodsmentioning

confidence: 99%

Status of the Vibrational Theory of Olfaction

et al. 2018

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The vibrational theory of olfaction is an attempt to describe a possible mechanism for olfaction which is explanatory and provides researchers with a set of principles which permit predictions allowing for structure-odor relations. Similar theories have occurred several times throughout olfactory science; this theory has again recently come to prominence by Luca Turin, who suggested that inelastic electron tunneling is the method by which vibrations are detected by the olfactory receptors within the hose. This work is intended to convey to the reader an up-to-date account of the vibrational theory of olfaction, both the historical iterations as well as the present iteration. This text is designed to give a chronological account of both theoretical and experimental studies on the topic, while providing context, comments, and background where they were found to be needed.

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Section: Methodsmentioning

confidence: 99%

Status of the Vibrational Theory of Olfaction

et al. 2018

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“…In addition, computational studies of the model compounds 20a and 20b were performed (Figs. 2 and 3) [30].…”

Section: Compoundmentioning

confidence: 99%

“…The silicon analogue disila-versalide (17b), and its derivatives 18b and 19b were synthesized according to Scheme 9, and the C/Si analogues 17a/17b -19a/19b were studied for their olfactory properties ( Table 7), their lipophilicity, and their biodegradability [30]. In addition, computational studies of the model compounds 20a and 20b were performed (Figs.…”

Section: Compoundmentioning

confidence: 99%

Odorant Design Based on the Carbon/Silicon Switch Strategy

Tacke

Metz

2008

Chemistry & Biodiversity

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Silicon chemistry has been demonstrated to be a novel source of chemical diversity in odorant design. The carbon/silicon switch strategy, i.e., sila-replacement in known odorants, is one of the methods currently used for the development of silicon-based odorants. Examples resulting from this strategy are sila-coranol, sila-dimetol, sila-linalool, sila-muguetalcohol, sila-majantol, sila-hydratropyl acetate, sila-bourgeonal, sila-lilial, disila-versalide, and disila-okoumal.

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“…These silicon compounds are derivatives of 1 a and 2 a that contain silicon atoms instead of the carbon atoms C5 and C8 in the 5,6,7,8-tetrahydro-2-naphthyl group (see also refs. [13j, 14,15]). We report here on the syntheses of disila-TTNPB (1 b) and disila-3-methyl-TTNPB (2 b) and on the pharmacological properties of the C/Si analogues 1 a/1 b and 2 a/2 b.…”

Section: Introductionmentioning

confidence: 99%

Silicon Analogues of the Retinoid Agonists TTNPB and 3‐Methyl‐TTNPB, Disila‐TTNPB and Disila‐3‐methyl‐TTNPB: Chemistry and Biology

Büttner¹,

Burschka²,

Daiß³

et al. 2007

ChemBioChem

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Twofold sila-substitution (C/Si exchange) in the saturated ring of the tetrahydronaphthalene skeleton of the retinoid agonists TTNPB (1 a) and 3-methyl-TTNPB (2 a) leads to disila-TTNPB (1 b) and disila-3-methyl-TTNPB (2 b), respectively. The silicon compounds 1 b and 2 b were synthesized in multiple steps, and their identities were established by elemental analyses, multinuclear NMR experiments, and single-crystal X-ray diffraction studies. Like TTNPB (1 a) and 3-methyl-TTNPB (2 a), the analogous silicon-based arotinoids 1 b and 2 b are strong pan-RAR agonists and display the same strong differentiation and apoptosis-inducing activity in NB4 promyelocytic leukemia cells as the parent carbon compounds. These results are in keeping with the nearly isomorphous structures of 1 a and 1 b bound to the complex of the RARbeta ligand-binding domain with the nuclear receptor (NR) box 2 peptide of the SRC-1 coactivator. The contacts within the ligand-binding pocket are identical except for helix H11, for which two turns are shifted in the disila-TTNPB (1 b) complex. This study represents the first comprehensive structure-function analysis of a carbon/silicon switch in a signaling molecule and demonstrates that silicon analogues can have the same biological functionalities and conserved structures as their parent carbon compounds, and it illustrates at the same time that silicon analogues of biologically active compounds have the potential to induce alternative allosteric effects, as in the case of helix H11, which might allow for novel options in drug design.

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Silicon Analogues of the Musk Odorant Versalide

Cited by 35 publications

References 8 publications

Status of the Vibrational Theory of Olfaction

Status of the Vibrational Theory of Olfaction

Odorant Design Based on the Carbon/Silicon Switch Strategy

Silicon Analogues of the Retinoid Agonists TTNPB and 3‐Methyl‐TTNPB, Disila‐TTNPB and Disila‐3‐methyl‐TTNPB: Chemistry and Biology

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