A Short Asymmetric Synthesis of (+)-Lyoniresinol Dimethyl Ether

Assoumatine, Tokouré; Datta, Probal K.; Hooper, Timothy S.; Yvon, Brigitte L.; Charlton, James L.

doi:10.1021/jo0497454

Cited by 24 publications

(14 citation statements)

References 23 publications

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“…This assignment was also supported by the NOESY correlations of H-7′ with H 2 -9′, and H-8′ with H-2′ (H-6)′. Finally, the negative optical rotation of 1 demonstrated the 7′ R ,8′ S absolute configuration of 1 [18,19]. Hence, compound 1 was defined as (−)-(7′ R ,8′ S )- N -[2-(4-hydroxyphenyl)-ethyl]-4,4′,9′-trihydroxy-3,5,3′,5′-tetramethoxy-2,7′-cyclolignan-7-en-9-amide.…”

Section: Resultsmentioning

confidence: 68%

Lignans from the Twigs of Litsea cubeba and Their Bioactivities

Xia

Wang

et al. 2019

Molecules

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Litsea cubeba, an important medicinal plant, is widely used as a traditional Chinese medicine and spice. Using cytotoxicity-guided fractionation, nine new lignans 1–9 and ten known analogues 10–19 were obtained from the EtOH extract of the twigs of L. cubeba. Their structures were assigned by extensive 1D- and 2D-NMR experiments, and the absolute configurations were resolved by specific rotation and a combination of experimental and theoretically calculated electronic circular dichroism (ECD) spectra. In the cytotoxicity assay, 7′,9-epoxylignans with feruloyl or cinnamoyl groups (compounds 7–9, 13 and 14) were selectively cytotoxic against NCI-H1650 cell line, while the dibenzylbutyrolactone lignans 17–19 exerted cytotoxicities against HCT-116 and A2780 cell lines. The results highlighted the structure-activity relationship importance of a feruloyl or a cinnamoyl moiety at C-9′ or/and C-7 ketone in 7′,9-epoxylignans. Furthermore, compound 11 was moderate active toward protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 13.5 μM, and compounds 4–6, 11 and 12 displayed inhibitory activity against LPS-induced NO production in RAW264.7 macrophages, with IC50 values of 46.8, 50.1, 58.6, 47.5, and 66.5 μM, respectively.

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Section: Resultsmentioning

confidence: 68%

Lignans from the Twigs of Litsea cubeba and Their Bioactivities

Xia

Wang

et al. 2019

Molecules

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“…Therefore, in this investigation, four azetidine-steroid derivatives were synthesized to evaluate their inotropic activity using a heart failure model. The first stage was achieved via preparation of an ether-steroid derivative (figure 1); it is important to mention that there are several methods for the preparation of ether groups which involve a series of reagents such as Me3SiCN, [25] K2CO3/acetone, [26] tetrahydrofuranlithium-aluminum hydride, [27] Me3SiCl, [28] K3PO4-DMF, [29] ethyl cinnamate [30] and others. In this investigation, an ether-steroid derivative (2) was prepared from estrone and p-nitrobenzoyl azide in the presence of dimethyl sulfoxide.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of new azetidine‐steroid derivative with inotropic activity in a heart failure model

Figueroa‐Valverde

María

Díaz-Cedillo

et al. 2020

Vietnam Journal of Chemistry

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Several steroid derivatives have prepared as inotropic drugs; however, there are few reports on azetidine‐steroid derivatives with inotropic activity. The aim of this study was to synthesize four azetidine‐steroid derivatives (compounds 3 to 6) to evaluate their biological activity on left ventricular pressure. The first stage was achieved by preparation of azetidine‐derivatives using reactions of etherification and addition. The second stage involves the evaluation of biological activity from azetidine derivatives on left ventricular pressure in a heart failure model using estrone as control. The results showed that only compound 3 increases left ventricular pressure compared with estrone, compounds 2 and 4 to 6. In conclusion, the positive inotropic effect exerted by compound 3 depends on the functional groups involved in their chemical structure.

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“…Aly (2003) used a strategy involving reaction of a diethyl phthalate with a 2-aminophenol derivative to generate the lactone and lactam functions. Assoumatine et al (2004) applied the analogous reaction of a succinate diester with aamino alcohol derivative. Conceptually the system might also be constructed from a phthaloyl -amino alcohol, for example (II), by intramolecular nucleophilic attack of the derived side chain alkoxide on a carbonyl group, involving carbon-oxygen bond formation followed by carbon-nitrogen bond cleavage to yield the eight-membered ring system (III).…”

Section: Commentmentioning

confidence: 99%

(S)-N-(1-Benzyl-2-hydroxyethyl)phthalamic acid

et al. 2005

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Key indicatorsSingle-crystal X-ray study T = 298 K Mean (C-C) = 0.012 Å Disorder in main residue R factor = 0.075 wR factor = 0.130 Data-to-parameter ratio = 8.3For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2005 International Union of Crystallography Printed in Great Britain -all rights reservedA feature of the structure of the title compound, C 17 H 17 NO 4 , is the three-dimensional connectivity generated by intermolecular hydrogen bonds.

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A Short Asymmetric Synthesis of (+)-Lyoniresinol Dimethyl Ether

Cited by 24 publications

References 23 publications

Lignans from the Twigs of Litsea cubeba and Their Bioactivities

Lignans from the Twigs of Litsea cubeba and Their Bioactivities

Design and synthesis of new azetidine‐steroid derivative with inotropic activity in a heart failure model

(S)-N-(1-Benzyl-2-hydroxyethyl)phthalamic acid

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